Enhanced Characterization of the Smell of Death by Comprehensive Two-Dimensional Gas Chromatography-Time-of-Flight Mass Spectrometry (GCxGC-TOFMS)
Identifieur interne : 000201 ( Pmc/Corpus ); précédent : 000200; suivant : 000202Enhanced Characterization of the Smell of Death by Comprehensive Two-Dimensional Gas Chromatography-Time-of-Flight Mass Spectrometry (GCxGC-TOFMS)
Auteurs : Jessica Dekeirsschieter ; Pierre-Hugues Stefanuto ; Catherine Brasseur ; Eric Haubruge ; Jean-François FocantSource :
- PLoS ONE [ 1932-6203 ] ; 2012.
Abstract
Soon after death, the decay process of mammalian soft tissues begins and leads to the release of cadaveric volatile compounds in the surrounding environment. The study of postmortem decomposition products is an emerging field of study in forensic science. However, a better knowledge of the smell of death and its volatile constituents may have many applications in forensic sciences. Domestic pigs are the most widely used human body analogues in forensic experiments, mainly due to ethical restrictions. Indeed, decomposition trials on human corpses are restricted in many countries worldwide. This article reports on the use of comprehensive two-dimensional gas chromatography coupled with time-of-flight mass spectrometry (GCxGC-TOFMS) for thanatochemistry applications. A total of 832 VOCs released by a decaying pig carcass in terrestrial ecosystem,
Url:
DOI: 10.1371/journal.pone.0039005
PubMed: 22723918
PubMed Central: 3377612
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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Enhanced Characterization of the Smell of Death by Comprehensive Two-Dimensional Gas Chromatography-Time-of-Flight Mass Spectrometry (GCxGC-TOFMS)</title><author><name sortKey="Dekeirsschieter, Jessica" sort="Dekeirsschieter, Jessica" uniqKey="Dekeirsschieter J" first="Jessica" last="Dekeirsschieter">Jessica Dekeirsschieter</name><affiliation><nlm:aff id="aff1"><addr-line>Department of Functional and Evolutionary Entomology, Gembloux Agro-Bio Tech, University of Liege, Gembloux, Belgium</addr-line></nlm:aff></affiliation></author><author><name sortKey="Stefanuto, Pierre Hugues" sort="Stefanuto, Pierre Hugues" uniqKey="Stefanuto P" first="Pierre-Hugues" last="Stefanuto">Pierre-Hugues Stefanuto</name><affiliation><nlm:aff id="aff2"><addr-line>Department of Chemistry, Organic and Biological Analytical Chemistry, CART, University of Liege, Liege, Belgium</addr-line></nlm:aff></affiliation></author><author><name sortKey="Brasseur, Catherine" sort="Brasseur, Catherine" uniqKey="Brasseur C" first="Catherine" last="Brasseur">Catherine Brasseur</name><affiliation><nlm:aff id="aff2"><addr-line>Department of Chemistry, Organic and Biological Analytical Chemistry, CART, University of Liege, Liege, Belgium</addr-line></nlm:aff></affiliation></author><author><name sortKey="Haubruge, Eric" sort="Haubruge, Eric" uniqKey="Haubruge E" first="Eric" last="Haubruge">Eric Haubruge</name><affiliation><nlm:aff id="aff1"><addr-line>Department of Functional and Evolutionary Entomology, Gembloux Agro-Bio Tech, University of Liege, Gembloux, Belgium</addr-line></nlm:aff></affiliation></author><author><name sortKey="Focant, Jean Francois" sort="Focant, Jean Francois" uniqKey="Focant J" first="Jean-François" last="Focant">Jean-François Focant</name><affiliation><nlm:aff id="aff2"><addr-line>Department of Chemistry, Organic and Biological Analytical Chemistry, CART, University of Liege, Liege, Belgium</addr-line></nlm:aff></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PMC</idno><idno type="pmid">22723918</idno><idno type="pmc">3377612</idno><idno type="url">http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3377612</idno><idno type="RBID">PMC:3377612</idno><idno type="doi">10.1371/journal.pone.0039005</idno><date when="2012">2012</date><idno type="wicri:Area/Pmc/Corpus">000201</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Corpus" wicri:corpus="PMC">000201</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">Enhanced Characterization of the Smell of Death by Comprehensive Two-Dimensional Gas Chromatography-Time-of-Flight Mass Spectrometry (GCxGC-TOFMS)</title><author><name sortKey="Dekeirsschieter, Jessica" sort="Dekeirsschieter, Jessica" uniqKey="Dekeirsschieter J" first="Jessica" last="Dekeirsschieter">Jessica Dekeirsschieter</name><affiliation><nlm:aff id="aff1"><addr-line>Department of Functional and Evolutionary Entomology, Gembloux Agro-Bio Tech, University of Liege, Gembloux, Belgium</addr-line></nlm:aff></affiliation></author><author><name sortKey="Stefanuto, Pierre Hugues" sort="Stefanuto, Pierre Hugues" uniqKey="Stefanuto P" first="Pierre-Hugues" last="Stefanuto">Pierre-Hugues Stefanuto</name><affiliation><nlm:aff id="aff2"><addr-line>Department of Chemistry, Organic and Biological Analytical Chemistry, CART, University of Liege, Liege, Belgium</addr-line></nlm:aff></affiliation></author><author><name sortKey="Brasseur, Catherine" sort="Brasseur, Catherine" uniqKey="Brasseur C" first="Catherine" last="Brasseur">Catherine Brasseur</name><affiliation><nlm:aff id="aff2"><addr-line>Department of Chemistry, Organic and Biological Analytical Chemistry, CART, University of Liege, Liege, Belgium</addr-line></nlm:aff></affiliation></author><author><name sortKey="Haubruge, Eric" sort="Haubruge, Eric" uniqKey="Haubruge E" first="Eric" last="Haubruge">Eric Haubruge</name><affiliation><nlm:aff id="aff1"><addr-line>Department of Functional and Evolutionary Entomology, Gembloux Agro-Bio Tech, University of Liege, Gembloux, Belgium</addr-line></nlm:aff></affiliation></author><author><name sortKey="Focant, Jean Francois" sort="Focant, Jean Francois" uniqKey="Focant J" first="Jean-François" last="Focant">Jean-François Focant</name><affiliation><nlm:aff id="aff2"><addr-line>Department of Chemistry, Organic and Biological Analytical Chemistry, CART, University of Liege, Liege, Belgium</addr-line></nlm:aff></affiliation></author></analytic><series><title level="j">PLoS ONE</title><idno type="eISSN">1932-6203</idno><imprint><date when="2012">2012</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><p>Soon after death, the decay process of mammalian soft tissues begins and leads to the release of cadaveric volatile compounds in the surrounding environment. The study of postmortem decomposition products is an emerging field of study in forensic science. However, a better knowledge of the smell of death and its volatile constituents may have many applications in forensic sciences. Domestic pigs are the most widely used human body analogues in forensic experiments, mainly due to ethical restrictions. Indeed, decomposition trials on human corpses are restricted in many countries worldwide. This article reports on the use of comprehensive two-dimensional gas chromatography coupled with time-of-flight mass spectrometry (GCxGC-TOFMS) for thanatochemistry applications. A total of 832 VOCs released by a decaying pig carcass in terrestrial ecosystem, <italic>i.e</italic>. a forest biotope, were identified by GCxGC-TOFMS. These postmortem compounds belong to many kinds of chemical class, mainly oxygen compounds (alcohols, acids, ketones, aldehydes, esters), sulfur and nitrogen compounds, aromatic compounds such as phenolic molecules and hydrocarbons. The use of GCxGC-TOFMS in study of postmortem volatile compounds instead of conventional GC-MS was successful.</p></div></front><back><div1 type="bibliography"><listBibl><biblStruct><analytic><author><name sortKey="Vass, Aa" uniqKey="Vass A">AA Vass</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Vass, Aa" uniqKey="Vass A">AA Vass</name></author><author><name sortKey="Barshick, Sa" uniqKey="Barshick S">SA Barshick</name></author><author><name sortKey="Sega, G" uniqKey="Sega G">G Sega</name></author><author><name sortKey="Caton, J" uniqKey="Caton J">J Caton</name></author><author><name sortKey="Skeen, Jt" uniqKey="Skeen J">JT Skeen</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Statheropoulos, M" uniqKey="Statheropoulos M">M Statheropoulos</name></author><author><name sortKey="Spiliopoulou, C" uniqKey="Spiliopoulou C">C Spiliopoulou</name></author><author><name sortKey="Agapiou, A" uniqKey="Agapiou A">A 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<front><journal-meta><journal-id journal-id-type="nlm-ta">PLoS One</journal-id><journal-id journal-id-type="iso-abbrev">PLoS ONE</journal-id><journal-id journal-id-type="publisher-id">plos</journal-id><journal-id journal-id-type="pmc">plosone</journal-id><journal-title-group><journal-title>PLoS ONE</journal-title></journal-title-group><issn pub-type="epub">1932-6203</issn><publisher><publisher-name>Public Library of Science</publisher-name><publisher-loc>San Francisco, USA</publisher-loc></publisher></journal-meta><article-meta><article-id pub-id-type="pmid">22723918</article-id><article-id pub-id-type="pmc">3377612</article-id><article-id pub-id-type="publisher-id">PONE-D-12-06649</article-id><article-id pub-id-type="doi">10.1371/journal.pone.0039005</article-id><article-categories><subj-group subj-group-type="heading"><subject>Research Article</subject></subj-group><subj-group subj-group-type="Discipline-v2"><subject>Biology</subject><subj-group><subject>Anatomy and Physiology</subject><subj-group><subject>Neurological System</subject><subj-group><subject>Sensory Physiology</subject></subj-group></subj-group></subj-group><subj-group><subject>Biochemistry</subject></subj-group><subj-group><subject>Zoology</subject></subj-group></subj-group><subj-group subj-group-type="Discipline-v2"><subject>Chemistry</subject><subj-group><subject>Analytical Chemistry</subject></subj-group><subj-group><subject>Applied Chemistry</subject></subj-group><subj-group><subject>Chemical Biology</subject></subj-group><subj-group><subject>Chromatography</subject></subj-group><subj-group><subject>Geochemistry</subject></subj-group><subj-group><subject>Medicinal Chemistry</subject></subj-group><subj-group><subject>Organic Chemistry</subject></subj-group></subj-group><subj-group subj-group-type="Discipline-v2"><subject>Medicine</subject><subj-group><subject>Mental Health</subject><subj-group><subject>Psychology</subject><subj-group><subject>Sensory Perception</subject></subj-group></subj-group></subj-group><subj-group><subject>Anatomy and Physiology</subject><subj-group><subject>Neurological System</subject><subj-group><subject>Sensory Physiology</subject></subj-group></subj-group><subj-group><subject>Sensory Systems</subject></subj-group></subj-group></subj-group><subj-group subj-group-type="Discipline-v2"><subject>Social and Behavioral Sciences</subject><subj-group><subject>Psychology</subject><subj-group><subject>Sensory Perception</subject></subj-group></subj-group></subj-group></article-categories><title-group><article-title>Enhanced Characterization of the Smell of Death by Comprehensive Two-Dimensional Gas Chromatography-Time-of-Flight Mass Spectrometry (GCxGC-TOFMS)</article-title><alt-title alt-title-type="running-head">Characterization of the Smell of Death</alt-title></title-group><contrib-group><contrib contrib-type="author"><name><surname>Dekeirsschieter</surname><given-names>Jessica</given-names></name><xref ref-type="aff" rid="aff1"><sup>1</sup></xref></contrib><contrib contrib-type="author"><name><surname>Stefanuto</surname><given-names>Pierre-Hugues</given-names></name><xref ref-type="aff" rid="aff2"><sup>2</sup></xref></contrib><contrib contrib-type="author"><name><surname>Brasseur</surname><given-names>Catherine</given-names></name><xref ref-type="aff" rid="aff2"><sup>2</sup></xref></contrib><contrib contrib-type="author"><name><surname>Haubruge</surname><given-names>Eric</given-names></name><xref ref-type="aff" rid="aff1"><sup>1</sup></xref></contrib><contrib contrib-type="author"><name><surname>Focant</surname><given-names>Jean-François</given-names></name><xref ref-type="aff" rid="aff2"><sup>2</sup></xref><xref ref-type="corresp" rid="cor1"><sup>*</sup></xref></contrib></contrib-group><aff id="aff1"><label>1</label><addr-line>Department of Functional and Evolutionary Entomology, Gembloux Agro-Bio Tech, University of Liege, Gembloux, Belgium</addr-line></aff><aff id="aff2"><label>2</label><addr-line>Department of Chemistry, Organic and Biological Analytical Chemistry, CART, University of Liege, Liege, Belgium</addr-line></aff><contrib-group><contrib contrib-type="editor"><name><surname>Matsunami</surname><given-names>Hiroaki</given-names></name><role>Editor</role><xref ref-type="aff" rid="edit1"></xref></contrib></contrib-group><aff id="edit1">Duke University, United States of America</aff><author-notes><corresp id="cor1">* E-mail: <email>JF.Focant@ulg.ac.be</email></corresp><fn fn-type="con"><p>Conceived and designed the experiments: JD EH JFF. Performed the experiments: JD PHS CB. Analyzed the data: JD PHS. Contributed reagents/materials/analysis tools: JD PHS CB EH JFF. Wrote the paper: JD PHS JFF.</p></fn></author-notes><pub-date pub-type="collection"><year>2012</year></pub-date><pub-date pub-type="epub"><day>18</day><month>6</month><year>2012</year></pub-date><volume>7</volume><issue>6</issue><elocation-id>e39005</elocation-id><history><date date-type="received"><day>5</day><month>3</month><year>2012</year></date><date date-type="accepted"><day>16</day><month>5</month><year>2012</year></date></history><permissions><copyright-statement>Dekeirsschieter et al. This is an open-access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited.</copyright-statement><copyright-year>2012</copyright-year></permissions><abstract><p>Soon after death, the decay process of mammalian soft tissues begins and leads to the release of cadaveric volatile compounds in the surrounding environment. The study of postmortem decomposition products is an emerging field of study in forensic science. However, a better knowledge of the smell of death and its volatile constituents may have many applications in forensic sciences. Domestic pigs are the most widely used human body analogues in forensic experiments, mainly due to ethical restrictions. Indeed, decomposition trials on human corpses are restricted in many countries worldwide. This article reports on the use of comprehensive two-dimensional gas chromatography coupled with time-of-flight mass spectrometry (GCxGC-TOFMS) for thanatochemistry applications. A total of 832 VOCs released by a decaying pig carcass in terrestrial ecosystem, <italic>i.e</italic>. a forest biotope, were identified by GCxGC-TOFMS. These postmortem compounds belong to many kinds of chemical class, mainly oxygen compounds (alcohols, acids, ketones, aldehydes, esters), sulfur and nitrogen compounds, aromatic compounds such as phenolic molecules and hydrocarbons. The use of GCxGC-TOFMS in study of postmortem volatile compounds instead of conventional GC-MS was successful.</p></abstract><counts><page-count count="16"></page-count></counts></article-meta></front><body><sec id="s1"><title>Introduction</title><p>The decay process of vertebrates begins rapidly after death (<italic>i.e.</italic> four minutes after death) <xref ref-type="bibr" rid="pone.0039005-Vass1">[1]</xref> and leads to the release of postmortem compounds in the ecosystem <xref ref-type="bibr" rid="pone.0039005-Vass2">[2]</xref>–<xref ref-type="bibr" rid="pone.0039005-Statheropoulos1">[3]</xref>. These cadaveric compounds, mainly volatile organic compounds (<italic>i.e.</italic> VOCs), are by- or end-products of the decay process <xref ref-type="bibr" rid="pone.0039005-Vass2">[2]</xref>, <xref ref-type="bibr" rid="pone.0039005-Packowski1">[4]</xref>. They come from the catabolism of the four major categories of biological macromolecules in living organisms: proteins, nucleic acid, lipids and carbohydrates <xref ref-type="bibr" rid="pone.0039005-Vass2">[2]</xref>–<xref ref-type="bibr" rid="pone.0039005-Statheropoulos1">[3]</xref>. The principal decay pathways and the metabolic origin of the main vertebrate postmortem volatiles were reviewed by Dent and colleagues <xref ref-type="bibr" rid="pone.0039005-Dent1">[5]</xref>, Boumba and colleagues <xref ref-type="bibr" rid="pone.0039005-Boumba1">[6]</xref> and recently by Paczkoski and Schütz <xref ref-type="bibr" rid="pone.0039005-Packowski1">[4]</xref>. However, the metabolic origin of many cadaveric compounds is still unknown <xref ref-type="bibr" rid="pone.0039005-Packowski1">[4]</xref>, <xref ref-type="bibr" rid="pone.0039005-Statheropoulos2">[7]</xref>. Only a few research groups have studied the postmortem VOCs emanating from human remains <xref ref-type="bibr" rid="pone.0039005-Vass3">[8]</xref>–<xref ref-type="bibr" rid="pone.0039005-DeGreef1">[13]</xref> and animal carcasses (pig <xref ref-type="bibr" rid="pone.0039005-Statheropoulos2">[7]</xref>, <xref ref-type="bibr" rid="pone.0039005-Dekeirsschieter1">[14]</xref>–<xref ref-type="bibr" rid="pone.0039005-Akdeniz1">[15]</xref>, mouse <xref ref-type="bibr" rid="pone.0039005-Kalinova1">[16]</xref>, rabbit <xref ref-type="bibr" rid="pone.0039005-Hdrich1">[17]</xref>). Nevertheless, the majority of these studies is focused on burial decomposition or in closed environments (“body bag”) and limits the access to the corpse for the necrofauna, mainly insects <xref ref-type="bibr" rid="pone.0039005-Statheropoulos2">[7]</xref>–<xref ref-type="bibr" rid="pone.0039005-Statheropoulos4">[11]</xref>. The available information concerning postmortem chemistry of above-ground decomposition is rather limited. Numerous applications would however benefit from a better understanding of the postmortem volatiles emitted during the decay process.</p><p>The cadaveric VOCs find applications in forensic sciences and the etiology of death <xref ref-type="bibr" rid="pone.0039005-Statheropoulos1">[3]</xref>, in training of cadaver dogs (human remains detection or HRD detection) <xref ref-type="bibr" rid="pone.0039005-Hoffman1">[12]</xref>–<xref ref-type="bibr" rid="pone.0039005-DeGreef1">[13]</xref>, <xref ref-type="bibr" rid="pone.0039005-Oesterhelweg1">[18]</xref>–<xref ref-type="bibr" rid="pone.0039005-Komar1">[20]</xref>, in the development of cadaveric material detection devices <xref ref-type="bibr" rid="pone.0039005-Vass3">[8]</xref>–<xref ref-type="bibr" rid="pone.0039005-Statheropoulos3">[10]</xref>, <xref ref-type="bibr" rid="pone.0039005-Hdrich1">[17]</xref> (electrochemical sensors (“electronic nose”) <xref ref-type="bibr" rid="pone.0039005-Vass3">[8]</xref>–<xref ref-type="bibr" rid="pone.0039005-Vass4">[9]</xref>, <xref ref-type="bibr" rid="pone.0039005-Hdrich1">[17]</xref>, <xref ref-type="bibr" rid="pone.0039005-Qu1">[21]</xref>, in exploiting insect olfaction (biosensor or biodetector <xref ref-type="bibr" rid="pone.0039005-Packowski1">[4]</xref>, <xref ref-type="bibr" rid="pone.0039005-LeBlanc1">[22]</xref>–<xref ref-type="bibr" rid="pone.0039005-Frederickx1">[23]</xref>) or in the determination of the post-mortem interval (PMI) <xref ref-type="bibr" rid="pone.0039005-Vass1">[1]</xref>, <xref ref-type="bibr" rid="pone.0039005-Statheropoulos1">[3]</xref>–<xref ref-type="bibr" rid="pone.0039005-Packowski1">[4]</xref>. The smell of death is constituted by a blend of chemical compounds changing over time and according to animal remains <xref ref-type="bibr" rid="pone.0039005-Vass3">[8]</xref>–<xref ref-type="bibr" rid="pone.0039005-Vass4">[9]</xref>, <xref ref-type="bibr" rid="pone.0039005-Dekeirsschieter1">[14]</xref>. Indeed, a recent study has shown that the odor of human remains is different from that of animals <xref ref-type="bibr" rid="pone.0039005-DeGreef1">[13]</xref>.</p><p>For the analysis of cadaveric VOCs, gas chromatography (GC) coupled to mass spectrometry (MS) is the technique of choice <xref ref-type="bibr" rid="pone.0039005-Statheropoulos1">[3]</xref>, <xref ref-type="bibr" rid="pone.0039005-Statheropoulos2">[7]</xref>–<xref ref-type="bibr" rid="pone.0039005-DeGreef1">[13]</xref>, <xref ref-type="bibr" rid="pone.0039005-Notter1">[24]</xref>. However, the volatile profile of the decomposition odor is constituted by a large number of VOCs <xref ref-type="bibr" rid="pone.0039005-Vass3">[8]</xref>–<xref ref-type="bibr" rid="pone.0039005-Vass4">[9]</xref> and GC easily suffers from peak capacity limitations. The complexity of volatile postmortem samples requires the use of more complex analytical methods. For example, GC is unable to detect quantitatively both short and long chain acids (<italic>e.g</italic>. present in decomposition fluid) due to the polarity difference in the molecules <xref ref-type="bibr" rid="pone.0039005-Swann1">[25]</xref>–<xref ref-type="bibr" rid="pone.0039005-Robards1">[26]</xref>. Comprehensive two-dimensional gas chromatography (GCxGC) has been developed to meet an increasing need for complex sample analysis and to address limitations such as peak capacity, dynamic range and restricted specificity of one-dimensional (conventional) GC systems (1D-GC) (<italic>i.e.</italic> to improve the global efficiency of the separation). GCxGC can be defined as a chromatographic technique during which a sample is subjected to two different separation processes coupled online <xref ref-type="bibr" rid="pone.0039005-Giddings1">[27]</xref> and as a result every compound is characterized by a retention time in each dimension (<sup>1</sup>t<sub>R</sub> and <sup>1</sup>t<sub>R</sub>) <xref ref-type="bibr" rid="pone.0039005-Packowski1">[4]</xref>. In practice, the end of the first dimension (<sup>1</sup>D) column is placed in a temperature controlled interface named ‘the modulator’ and further serially connected to the second dimension (<sup>2</sup>D) column. The cryogenic modulator ensures high sampling rates and transfer of the sample to <sup>2</sup>D column <xref ref-type="bibr" rid="pone.0039005-Ledford1">[28]</xref>. The entire <sup>1</sup>D chromatogram is thus ‘sliced’ following a modulation period (P<sub>M</sub>) of a few seconds and sent into <sup>2</sup>D for a fast GC-type separation, resulting in peak widths of 200–600 ms <xref ref-type="bibr" rid="pone.0039005-Focant1">[29]</xref>. By fine-tuning of the GC phase combination, compounds potentially still coeluting at the end of the <sup>1</sup>D separation can be separated on the basis of their different behavior as regards of the <sup>2</sup>D phase. Globally, the separation power is increased and the sensitivity is also enhanced by cryogenic zone compression <xref ref-type="bibr" rid="pone.0039005-Phillips1">[30]</xref>, <xref ref-type="bibr" rid="pone.0039005-Patterson1">[31]</xref>. In terms of detector, in addition to flame-ionization and other element selective detectors, various mass-spectrometric (MS) detectors, providing structural information (an additional dimension), can be used since the first coupling was reported in early 2000 <xref ref-type="bibr" rid="pone.0039005-vanDeursen1">[32]</xref>. Although double focusing sector, quadrupole, and ion traps are popular MS detectors for GC, they have limited use in GCxGC because of their relatively slow scanning rates, compared to fast acquisition time-of-flight (TOF) MS better suited to characterize very narrow <sup>2</sup>D peaks. Additionally, the absence of concentration skewing in the TOFMS instrument ensures spectral continuity and allows mass spectral deconvolution of coeluting chromatographic peaks characterized by different fragmentation patterns <xref ref-type="bibr" rid="pone.0039005-Focant2">[33]</xref>. This capability allows the identification of different compounds if the peak apexes of coeluting analytes are at least separated by three scans and differ somewhat in their mass spectra. The use of deconvoluted ion current (DIC) makes the TOFMS almost like a third dimension for the separation system. Consequently, the GC×GC–TOFMS coupling is a powerful instrument combining improved chromatographic resolution of the GC × GC and the analytical resolving power of the TOFMS <xref ref-type="bibr" rid="pone.0039005-Focant3">[34]</xref>–<xref ref-type="bibr" rid="pone.0039005-Focant4">[35]</xref>. GCxGC-TOFMS, has thus been used to analyze complex samples in various fields <xref ref-type="bibr" rid="pone.0039005-Semard1">[36]</xref>, including VOC analyses <xref ref-type="bibr" rid="pone.0039005-Cardeal1">[37]</xref>–<xref ref-type="bibr" rid="pone.0039005-Cordero1">[39]</xref>.</p><table-wrap id="pone-0039005-t001" position="float"><object-id pub-id-type="doi">10.1371/journal.pone.0039005.t001</object-id><label>Table 1</label><caption><title>The five decompositional stages defined in this study and their descriptions.</title></caption><alternatives><graphic id="pone-0039005-t001-1" xlink:href="pone.0039005.t001"></graphic><table frame="hsides" rules="groups"><colgroup span="1"><col align="left" span="1"></col><col align="center" span="1"></col><col align="center" span="1"></col></colgroup><thead><tr><td align="left" rowspan="1" colspan="1">Decompositional stage</td><td align="left" rowspan="1" colspan="1">Description</td><td align="left" rowspan="1" colspan="1">Literature report</td></tr></thead><tbody><tr><td align="left" rowspan="1" colspan="1">(1) <italic>Fresh</italic></td><td align="left" rowspan="1" colspan="1">From death until the first signs of bloating</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Vass1">[1]</xref>, <xref ref-type="bibr" rid="pone.0039005-GillKing1">[49]</xref>, <xref ref-type="bibr" rid="pone.0039005-Gennard1">[52]</xref>, <xref ref-type="bibr" rid="pone.0039005-Reed1">[54]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1">Autolysis</td><td align="left" rowspan="1" colspan="1"></td></tr><tr><td align="left" rowspan="1" colspan="1">(2) <italic>Bloated</italic></td><td align="left" rowspan="1" colspan="1">Putrefaction mechanism generates accumulation of breakdown gases causingbloating of the corpse. The first signs of the bloated stage appear in the abdomen.Then the whole body swells</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Vass1">[1]</xref>, <xref ref-type="bibr" rid="pone.0039005-Gennard1">[52]</xref>, <xref ref-type="bibr" rid="pone.0039005-Reed1">[54]</xref>, <xref ref-type="bibr" rid="pone.0039005-Galloway1">[56]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1">Anaerobic fermentations</td><td align="left" rowspan="1" colspan="1"></td></tr><tr><td align="left" rowspan="1" colspan="1">(3) <italic>Active decay</italic></td><td align="left" rowspan="1" colspan="1">Darkening of the skin</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Vass1">[1]</xref>, <xref ref-type="bibr" rid="pone.0039005-Gennard1">[52]</xref>, <xref ref-type="bibr" rid="pone.0039005-Reed1">[54]</xref>, <xref ref-type="bibr" rid="pone.0039005-Galloway1">[56]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1">The skin is breaking up and the body began to deflate. Protein sources arebroken down into fatty acids and other decomposition products such as skatole,indole, cadaverine, putrescine</td><td align="left" rowspan="1" colspan="1"></td></tr><tr><td align="left" rowspan="1" colspan="1">(4) <italic>Advanced decay</italic></td><td align="left" rowspan="1" colspan="1">Corpse dries and the remains are skin, cartilage, hair, bones and some fragmentsof flesh</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Gennard1">[52]</xref>, <xref ref-type="bibr" rid="pone.0039005-Reed1">[54]</xref>, <xref ref-type="bibr" rid="pone.0039005-Galloway1">[56]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1">(5) <italic>Dry remains or skeletonisation</italic></td><td align="left" rowspan="1" colspan="1">The only remains are bones and hair</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Gennard1">[52]</xref>, <xref ref-type="bibr" rid="pone.0039005-Reed1">[54]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1">Diagenesis</td><td align="left" rowspan="1" colspan="1"></td></tr></tbody></table></alternatives></table-wrap><fig id="pone-0039005-g001" position="float"><object-id pub-id-type="doi">10.1371/journal.pone.0039005.g001</object-id><label>Figure 1</label><caption><title>Temperature recordings in the forest biotope on the lateral cage of the pig carcass.</title></caption><graphic xlink:href="pone.0039005.g001"></graphic></fig><fig id="pone-0039005-g002" position="float"><object-id pub-id-type="doi">10.1371/journal.pone.0039005.g002</object-id><label>Figure 2</label><caption><title>Typical decay stages followed by the pig carcass in a forest biotope.</title></caption><graphic xlink:href="pone.0039005.g002"></graphic></fig><fig id="pone-0039005-g003" position="float"><object-id pub-id-type="doi">10.1371/journal.pone.0039005.g003</object-id><label>Figure 3</label><caption><title>GCxGC-TOFMS apex plot of a sample (1<sup>st</sup> of May) of the advanced decay stage.</title><p>All t<sub>R</sub> are in seconds. (A) 633 hits were identified after raw data processing. (B) 218 peaks were identified after removal of column bleed (rectangle region), solvent signals (circled region), and analytes present in the reference blank samples. (C) chromatographic distribution of the 42 specific VOC compounds present in that particular sample and in at least three other samples (♦Alcohols; + Aldehydes; ○ Amides; • Amines; △ Aromatic compounds; Υ Carboxylic acids; × Ester; – Ketones; ▴ Sulfur compounds; − Others compounds).</p></caption><graphic xlink:href="pone.0039005.g003"></graphic></fig><table-wrap id="pone-0039005-t002" position="float"><object-id pub-id-type="doi">10.1371/journal.pone.0039005.t002</object-id><label>Table 2</label><caption><title>List of occurrences for the detected postmortem chemical compounds by GCxGC-TOFMS.</title></caption><alternatives><graphic id="pone-0039005-t002-2" xlink:href="pone.0039005.t002"></graphic><table frame="hsides" rules="groups"><colgroup span="1"><col align="left" span="1"></col><col align="center" span="1"></col><col align="center" span="1"></col><col align="center" span="1"></col><col align="center" span="1"></col></colgroup><thead><tr><td align="left" rowspan="1" colspan="1">8 occurrences</td><td align="left" rowspan="1" colspan="1">7 occurrences</td><td align="left" rowspan="1" colspan="1">6 occurrences</td><td align="left" rowspan="1" colspan="1">5 occurrences</td><td align="left" rowspan="1" colspan="1">4 occurrences</td></tr></thead><tbody><tr><td align="left" rowspan="1" colspan="1">✓1H-indole</td><td align="left" rowspan="1" colspan="1">✓1-Pentene, 2-methyl-</td><td align="left" rowspan="1" colspan="1">✓1-Butanol</td><td align="left" rowspan="1" colspan="1">✓1-Octanol</td><td align="left" rowspan="1" colspan="1">✓1-Hexen-3-ol</td></tr><tr><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1">✓1,2,3-Propanetriol</td><td align="left" rowspan="1" colspan="1">✓Butanoic acid</td><td align="left" rowspan="1" colspan="1">✓1-Propanol, 2-methyl-</td><td align="left" rowspan="1" colspan="1">✓1-Pentanol, 4-methyl-</td></tr><tr><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1">✓Ethanol</td><td align="left" rowspan="1" colspan="1">✓Propanoic acid, 2-methyl-</td><td align="left" rowspan="1" colspan="1">✓Butanoic acid, 2-methyl</td><td align="left" rowspan="1" colspan="1">✓2-Hexanol</td></tr><tr><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1">✓Phenol, 4-methyl-</td><td align="left" rowspan="1" colspan="1">✓Disulfide, dimethyl</td><td align="left" rowspan="1" colspan="1">✓Butanoic acid, 3-methyl</td><td align="left" rowspan="1" colspan="1">✓2-Hexen-1-ol</td></tr><tr><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1">✓Acetaldehyde</td><td align="left" rowspan="1" colspan="1">✓Trisulfide, dimethyl</td><td align="left" rowspan="1" colspan="1">✓Pentanoic acid</td><td align="left" rowspan="1" colspan="1">✓Hexanoic acid</td></tr><tr><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1">✓1-Butanamine, 3-methyl-</td><td align="left" rowspan="1" colspan="1">✓Benzenemethanol, à-methyl-</td><td align="left" rowspan="1" colspan="1">✓Pentanoic acid, 4-methyl-</td></tr><tr><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1">✓2-Propanol, 1-amino-</td><td align="left" rowspan="1" colspan="1">✓Pyrazine, tetramethyl-</td><td align="left" rowspan="1" colspan="1">✓Naphthalene, 2,6-diisopropyl</td></tr><tr><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1">✓Formamide, N-butyl-</td><td align="left" rowspan="1" colspan="1">✓Pyrazine, trimethyl-</td><td align="left" rowspan="1" colspan="1">✓Quinazoline, 2,4-dimethyl-</td></tr><tr><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1">✓Formamide, N,N-dimethyl-</td><td align="left" rowspan="1" colspan="1">✓1-Butanol, 4-Amino-</td><td align="left" rowspan="1" colspan="1">✓Quinoline</td></tr><tr><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1">✓1,3-Dioxolane, 2-acetyl-</td><td align="left" rowspan="1" colspan="1">✓Formamide, N-methyl-</td><td align="left" rowspan="1" colspan="1">✓Acetic acid, ethyl ester</td></tr><tr><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1">✓Trimethylamine</td><td align="left" rowspan="1" colspan="1">✓Butanoic acid, 3-methyl-, butyl ester</td></tr><tr><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1">✓Nonanal</td><td align="left" rowspan="1" colspan="1">✓Dothiepin*</td></tr><tr><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1">✓2-Octanone</td><td align="left" rowspan="1" colspan="1">✓2-Piperidinone</td></tr><tr><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1">✓2-Undecanone</td><td align="left" rowspan="1" colspan="1">✓Acetamide, N-methyl-</td></tr><tr><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1">✓Butyl isocyanatoacetate</td><td align="left" rowspan="1" colspan="1">✓Butanamide</td></tr><tr><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1">✓Hydroperoxide, 1-ethylbutyl</td><td align="left" rowspan="1" colspan="1">✓Formamide, N-phenyl-</td></tr><tr><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1">✓Hexanamide, N-methyl</td></tr><tr><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1">✓Methanamine, N,N-dimethyl-</td></tr><tr><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1">✓Benzaldehyde</td></tr><tr><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1">✓Heptanal</td></tr><tr><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1">✓Nonenal</td></tr><tr><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1">✓Propanal, 2,2-dimethyl-</td></tr><tr><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1">✓2-Nonanone</td></tr><tr><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1">✓3-Octanone</td></tr><tr><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1">✓Cyclohexanone</td></tr><tr><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1">✓Ethanone, 1-phenyl-</td></tr><tr><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1">✓Propane, 1-bromo-2-methyl-</td></tr><tr><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1">✓Hydroperoxide, 1-methylbutyl</td></tr><tr><td align="left" rowspan="1" colspan="1"><bold>1 compound</bold></td><td align="left" rowspan="1" colspan="1"><bold>5 compounds</bold></td><td align="left" rowspan="1" colspan="1"><bold>10 compounds</bold></td><td align="left" rowspan="1" colspan="1"><bold>16 compounds</bold></td><td align="left" rowspan="1" colspan="1"><bold>28 compounds</bold></td></tr></tbody></table></alternatives><table-wrap-foot><fn id="nt101"><label></label><p>•Dothiepin is not considered as a cadaveric compound.</p></fn></table-wrap-foot></table-wrap><p>Here, we report on a first field trial using GCxGC-TOFMS for the study of postmortem VOCs released by above-ground decomposition of pig carcasses, using it as a human body analogue.</p></sec><sec sec-type="materials|methods" id="s2"><title>Materials and Methods</title><sec id="s2a"><title>1. Animal Model and Field Site</title><p>Domestic pig (<italic>Sus scrofa domesticus</italic> L.) (25 kg) was used to surrogate human models mainly for physiological, biochemical, ethical, legal and economic reasons <xref ref-type="bibr" rid="pone.0039005-Swann1">[25]</xref>, <xref ref-type="bibr" rid="pone.0039005-Grassberger1">[40]</xref>–<xref ref-type="bibr" rid="pone.0039005-Schoenly1">[45]</xref>. Unlike other animals, pigs are considered to be an acceptable substitute due to their similarity to humans in body mass (torso in weight), skin structure, fat to muscle ratio and hair coverage <xref ref-type="bibr" rid="pone.0039005-Dent1">[5]</xref>, <xref ref-type="bibr" rid="pone.0039005-Swann1">[25]</xref>, <xref ref-type="bibr" rid="pone.0039005-Schoenly1">[45]</xref>–<xref ref-type="bibr" rid="pone.0039005-Schotsmans1">[46]</xref>. The greatest dissimilarity between pigs and humans are the bones, which have a different microstructure <xref ref-type="bibr" rid="pone.0039005-Schotsmans1">[46]</xref>–<xref ref-type="bibr" rid="pone.0039005-Harsanyi1">[47]</xref>. The piglet was killed by a penetrative captive bolt and disposed in the experimental site within the next 4 hours. Immediately after the euthanasia, the pig carcass was packed in a double plastic bag to avoid any insect colonization before laying on the experimental biotope. This study was approved by the committee on the Ethics of Animal Experiments of the University Faculty of Agricultural Sciences of Gembloux (since 2009, Gembloux Agro-Bio Tech, University of Liege).</p><p>The study site was a forest biotope, located in Belgium (Lambert-coordinates: 141512.00/149844.00) with pedunculate oaks (<italic>Quercus robur</italic> L.), European beeches (<italic>Fagus sylvatica</italic> L.) and sycamore maples (<italic>Acer pseudoplatanus</italic> L.). This field study was conducted with the permission of the forest administrator.</p><p>The decaying pig was placed in metal mesh cages (180 cm×90 cm×90 cm) to avoid scavenging by carnivores. The experiment was conducted during six weeks in spring 2007 (March 29-May 11). As control samples, volatile collection of the atmospheric VOCs was performed simultaneously to the pig samples, at 50 m from the decomposing swine carcass.</p><p>As temperature is one of the most important parameters influencing the decomposition rate <xref ref-type="bibr" rid="pone.0039005-Vass1">[1]</xref>–<xref ref-type="bibr" rid="pone.0039005-Vass2">[2]</xref>, <xref ref-type="bibr" rid="pone.0039005-Anderson2">[48]</xref>–<xref ref-type="bibr" rid="pone.0039005-Campobasso1">[50]</xref>, the ambient air temperature was automatically measured once an hour using a data logger (Testo 175-T1® temperature data logger, Germany) placed on the lateral side of the cage, at a height of 75 cm. The daily mean temperature was calculated on the basis of ambient air temperature recorded at a time interval of 24 hours. Other environmental parameters (humidity, wind velocity, wind direction) were recorded thanks to Vantage Pro Plus™ Stations® (Davis, Hayward, CA, USA).</p><fig id="pone-0039005-g004" position="float"><object-id pub-id-type="doi">10.1371/journal.pone.0039005.g004</object-id><label>Figure 4</label><caption><title>Number of released compounds according to the decay stages and postmortem time.</title></caption><graphic xlink:href="pone.0039005.g004"></graphic></fig><fig id="pone-0039005-g005" position="float"><object-id pub-id-type="doi">10.1371/journal.pone.0039005.g005</object-id><label>Figure 5</label><caption><title>Spatial distribution of Y-variables in a score-plot based on relative area of VOCs.</title></caption><graphic xlink:href="pone.0039005.g005"></graphic></fig><fig id="pone-0039005-g006" position="float"><object-id pub-id-type="doi">10.1371/journal.pone.0039005.g006</object-id><label>Figure 6</label><caption><title>Distribution of chemical classes according to postmortem time (days).</title></caption><graphic xlink:href="pone.0039005.g006"></graphic></fig><table-wrap id="pone-0039005-t003" position="float"><object-id pub-id-type="doi">10.1371/journal.pone.0039005.t003</object-id><label>Table 3</label><caption><title>Volatile chemicals released in the headspace of decaying pig carcass according to the decay stages, ordered by chemical families.</title></caption><alternatives><graphic id="pone-0039005-t003-3" xlink:href="pone.0039005.t003"></graphic><table frame="hsides" rules="groups"><colgroup span="1"><col align="left" span="1"></col><col align="center" span="1"></col><col align="center" span="1"></col><col align="center" span="1"></col><col align="center" span="1"></col><col align="center" span="1"></col></colgroup><thead><tr><td align="left" rowspan="1" colspan="1">VOCs</td><td colspan="4" align="left" rowspan="1">Decay stages</td><td align="left" rowspan="1" colspan="1">Literature report</td></tr><tr><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1">Fresh</td><td align="left" rowspan="1" colspan="1">Bloated</td><td align="left" rowspan="1" colspan="1">Active decay</td><td align="left" rowspan="1" colspan="1">Advanced decay</td><td align="left" rowspan="1" colspan="1"></td></tr></thead><tbody><tr><td align="left" rowspan="1" colspan="1"><bold>Alkanes</bold></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td></tr><tr><td align="left" rowspan="1" colspan="1">Butane</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Hdrich1">[17]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1">Cyclopentane, butyl-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Dodecane</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Statheropoulos2">[7]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1">Eicosane</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Dekeirsschieter1">[14]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1">Heneicosane</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Heptacosane</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Heptane, 2,4-dimethyl-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Statheropoulos1">[3]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1">Hexadecane</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Prada1">[59]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1">Nonane</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Statheropoulos2">[7]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1">Octane</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Statheropoulos1">[3]</xref>, <xref ref-type="bibr" rid="pone.0039005-Statheropoulos3">[10]</xref>–<xref ref-type="bibr" rid="pone.0039005-Statheropoulos4">[11]</xref>, <xref ref-type="bibr" rid="pone.0039005-Hdrich1">[17]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1">Tetradecane</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Statheropoulos2">[7]</xref>, <xref ref-type="bibr" rid="pone.0039005-Prada1">[59]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1">Tricosane</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Tridecane, 4-methyl-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Undecane</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Statheropoulos2">[7]</xref>–<xref ref-type="bibr" rid="pone.0039005-Vass4">[9]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1">Undecane, 2,5-dimethyl-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1"><bold>Alkenes</bold></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td></tr><tr><td align="left" rowspan="1" colspan="1">1-Butene, 3-methyl-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">1-Decene</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">1-Pentene, 2-methyl-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">1,3,6-Octatriene, 3,7-dimethyl-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">α-Phellandrene</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">α-Pinene</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Statheropoulos1">[3]</xref>, <xref ref-type="bibr" rid="pone.0039005-Statheropoulos2">[7]</xref>, <xref ref-type="bibr" rid="pone.0039005-Akdeniz1">[15]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1">γ-Terpinene</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">α-Thujene</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">o-Xylene</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Statheropoulos1">[3]</xref>, <xref ref-type="bibr" rid="pone.0039005-Statheropoulos2">[7]</xref>, <xref ref-type="bibr" rid="pone.0039005-Vass4">[9]</xref>, <xref ref-type="bibr" rid="pone.0039005-Statheropoulos4">[11]</xref>, <xref ref-type="bibr" rid="pone.0039005-DeGreef1">[13]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1">p-Xylene</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Statheropoulos1">[3]</xref>, <xref ref-type="bibr" rid="pone.0039005-Vass3">[8]</xref>–<xref ref-type="bibr" rid="pone.0039005-DeGreef1">[13]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1"><bold>Alcohols</bold></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td></tr><tr><td align="left" rowspan="1" colspan="1">1-Butanol</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Statheropoulos1">[3]</xref>–<xref ref-type="bibr" rid="pone.0039005-Dent1">[5]</xref>, <xref ref-type="bibr" rid="pone.0039005-Statheropoulos2">[7]</xref>, <xref ref-type="bibr" rid="pone.0039005-DeGreef1">[13]</xref>–<xref ref-type="bibr" rid="pone.0039005-Dekeirsschieter1">[14]</xref>, <xref ref-type="bibr" rid="pone.0039005-Hdrich1">[17]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1">1-Heptanol</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Akdeniz1">[15]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1">1-Hexanol</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Statheropoulos1">[3]</xref>–<xref ref-type="bibr" rid="pone.0039005-Packowski1">[4]</xref>, <xref ref-type="bibr" rid="pone.0039005-Statheropoulos2">[7]</xref>, <xref ref-type="bibr" rid="pone.0039005-Hoffman1">[12]</xref>–<xref ref-type="bibr" rid="pone.0039005-DeGreef1">[13]</xref>, <xref ref-type="bibr" rid="pone.0039005-Akdeniz1">[15]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1">1-Hexen-3-ol</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">1-Octanol</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Packowski1">[4]</xref>, <xref ref-type="bibr" rid="pone.0039005-Hoffman1">[12]</xref>–<xref ref-type="bibr" rid="pone.0039005-DeGreef1">[13]</xref>, <xref ref-type="bibr" rid="pone.0039005-Akdeniz1">[15]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1">1-Pentanol</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Statheropoulos1">[3]</xref>–<xref ref-type="bibr" rid="pone.0039005-Packowski1">[4]</xref>, <xref ref-type="bibr" rid="pone.0039005-Boumba1">[6]</xref>, <xref ref-type="bibr" rid="pone.0039005-Vass4">[9]</xref>, <xref ref-type="bibr" rid="pone.0039005-Hoffman1">[12]</xref>–<xref ref-type="bibr" rid="pone.0039005-Dekeirsschieter1">[14]</xref>, <xref ref-type="bibr" rid="pone.0039005-Hdrich1">[17]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1">1-Pentanol, 4-methyl-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">1-Propanol, 2-methyl-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Statheropoulos1">[3]</xref>–<xref ref-type="bibr" rid="pone.0039005-Packowski1">[4]</xref>, <xref ref-type="bibr" rid="pone.0039005-Boumba1">[6]</xref>–<xref ref-type="bibr" rid="pone.0039005-Statheropoulos2">[7]</xref>, <xref ref-type="bibr" rid="pone.0039005-Dekeirsschieter1">[14]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1">1-Tridecanol</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">1,2,3-Propanetriol</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">2-Hexanol</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">2-Hexen-1-ol</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">3-Hexanol</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">3-Hexene-2,5-diol</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">7-Octen-4-ol</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Cyclohexanol</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Cyclopentanedecaol</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Ethanol</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Statheropoulos1">[3]</xref>–<xref ref-type="bibr" rid="pone.0039005-Boumba1">[6]</xref>, <xref ref-type="bibr" rid="pone.0039005-Statheropoulos4">[11]</xref>, <xref ref-type="bibr" rid="pone.0039005-DeGreef1">[13]</xref>–<xref ref-type="bibr" rid="pone.0039005-Akdeniz1">[15]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1"><bold>carboxylic acids</bold></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td></tr><tr><td align="left" rowspan="1" colspan="1">2,3-Dihydroxysuccinic acid</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">3-Pentenoic acid, 4-methyl-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Butanoic acid</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Vass1">[1]</xref>, <xref ref-type="bibr" rid="pone.0039005-Statheropoulos1">[3]</xref>–<xref ref-type="bibr" rid="pone.0039005-Dent1">[5]</xref>, <xref ref-type="bibr" rid="pone.0039005-Hoffman1">[12]</xref>–<xref ref-type="bibr" rid="pone.0039005-Dekeirsschieter1">[14]</xref>, <xref ref-type="bibr" rid="pone.0039005-Hdrich1">[17]</xref>, <xref ref-type="bibr" rid="pone.0039005-Swann1">[25]</xref>, <xref ref-type="bibr" rid="pone.0039005-GillKing1">[49]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1">Butanoic acid, 2-methyl</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Statheropoulos1">[3]</xref>, <xref ref-type="bibr" rid="pone.0039005-Vass4">[9]</xref>, <xref ref-type="bibr" rid="pone.0039005-Dekeirsschieter1">[14]</xref>, <xref ref-type="bibr" rid="pone.0039005-Hdrich1">[17]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1">Butanoic acid, 3-methyl- (iso-valeric)</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Dekeirsschieter1">[14]</xref>, <xref ref-type="bibr" rid="pone.0039005-Swann1">[25]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1">Butyric acid, γ-amino-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Heptanoic acid</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Hexadecanoic acid (palimitic)</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Vass2">[2]</xref>, <xref ref-type="bibr" rid="pone.0039005-Packowski1">[4]</xref>, <xref ref-type="bibr" rid="pone.0039005-Swann1">[25]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1">Hexanoic acid (caproic)</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Packowski1">[4]</xref>, <xref ref-type="bibr" rid="pone.0039005-Hoffman1">[12]</xref>–<xref ref-type="bibr" rid="pone.0039005-Dekeirsschieter1">[14]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1">Isobutanoic acid, α-Amino</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Octanoic acid (caprylic)</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Vass2">[2]</xref>, <xref ref-type="bibr" rid="pone.0039005-DeGreef1">[13]</xref>–<xref ref-type="bibr" rid="pone.0039005-Dekeirsschieter1">[14]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1">Pentanoic acid (valeric)</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Hoffman1">[12]</xref>–<xref ref-type="bibr" rid="pone.0039005-Dekeirsschieter1">[14]</xref>, <xref ref-type="bibr" rid="pone.0039005-Swann1">[25]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1">Pentanoic acid, 4-methyl- (iso-caproic)</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Dekeirsschieter1">[14]</xref>, <xref ref-type="bibr" rid="pone.0039005-Swann1">[25]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1">Propanoic acid, 2-methyl- (iso-butyric)</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Dekeirsschieter1">[14]</xref>, <xref ref-type="bibr" rid="pone.0039005-Swann1">[25]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1">Propanoic acid, 2,2-dimethyl-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">succinic acid, 2,3-dihydroxy-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1"><bold>Aromatic coumpounds</bold></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td></tr><tr><td align="left" rowspan="1" colspan="1">1(3H)-Isobenzofuranone</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">1H-Indole</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Statheropoulos1">[3]</xref>–<xref ref-type="bibr" rid="pone.0039005-Dent1">[5]</xref>, <xref ref-type="bibr" rid="pone.0039005-Hoffman1">[12]</xref>–<xref ref-type="bibr" rid="pone.0039005-Akdeniz1">[15]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1">1H-Indole, 3-methyl-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">1H-Pyrrole, 2,5-dimethyl-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Benzene, 1-methyl-4-(1-methylethyl)-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Dekeirsschieter1">[14]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1">Benzene, 1-methylethyl-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Benzene, ethyl-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Benzene, methyl-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Benzeneethanol</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Benzenemethanol</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Benzenemethanol, α-methyl-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Furan, 2-pentyl-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Hoffman1">[12]</xref>–<xref ref-type="bibr" rid="pone.0039005-DeGreef1">[13]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1">Isoquinoline</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Naphthalene</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Packowski1">[4]</xref>, <xref ref-type="bibr" rid="pone.0039005-Statheropoulos2">[7]</xref>–<xref ref-type="bibr" rid="pone.0039005-Vass4">[9]</xref>, <xref ref-type="bibr" rid="pone.0039005-Statheropoulos4">[11]</xref>, <xref ref-type="bibr" rid="pone.0039005-DeGreef1">[13]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1">Naphthalene, 2,6-diisopropyl</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Phenol, 2-ethyl-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Phenol, 4-ethyl-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Akdeniz1">[15]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1">Phenol, 4-methyl-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Packowski1">[4]</xref>, <xref ref-type="bibr" rid="pone.0039005-Statheropoulos4">[11]</xref>, <xref ref-type="bibr" rid="pone.0039005-DeGreef1">[13]</xref>–<xref ref-type="bibr" rid="pone.0039005-Akdeniz1">[15]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1">2-phenylethanol</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Dekeirsschieter1">[14]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1">Pyrazine, 2-butyl-3,5-dimethyl</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Pyrazine, 2,3-dimethyl-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Pyrazine, 2,5-dimethyl-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Pyrazine, 2,6-dimethyl-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Pyrazine, 3-ethyl-2,5-dimethyl-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Pyrazine, 3,5-diethyl-2-methyl-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Pyrazine, methyl-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Pyrazine, tetramethyl-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Pyrazine, trimethyl-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Dekeirsschieter1">[14]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1">Pyridine, 2-methyl-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Pyridine, 2,6-dimethyl-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Quinazoline</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Dekeirsschieter1">[14]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1">Quinazoline, 2,4-dimethyl-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Quinazoline, 4-methyl-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Quinoline</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1"><bold>Esters</bold></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td></tr><tr><td align="left" rowspan="1" colspan="1">1,2-Benzenedicarboxylic acid, dihexyl ester</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">2-Propenoic acid, 3-methoxybutyl ester</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">3-Hexen-1-ol, acetate</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">3-octanyl acetate</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Acetic acid, butoxyhydroxy-, butyl ester</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Acetic acid, ethyl ester</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Statheropoulos1">[3]</xref>, <xref ref-type="bibr" rid="pone.0039005-Statheropoulos2">[7]</xref>, <xref ref-type="bibr" rid="pone.0039005-Hdrich1">[17]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1">Allyl tert-Butyl carbonate</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Butanoic acid, 1-methylpropyl ester</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Butanoic acid, 3-methyl-, butyl ester</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Butanoic acid, butyl ester</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Packowski1">[4]</xref>, <xref ref-type="bibr" rid="pone.0039005-Vass4">[9]</xref>, <xref ref-type="bibr" rid="pone.0039005-Hoffman1">[12]</xref>, <xref ref-type="bibr" rid="pone.0039005-Dekeirsschieter1">[14]</xref>, <xref ref-type="bibr" rid="pone.0039005-Hdrich1">[17]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1">Butyl 2-methylbutanoate</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Dekeirsschieter1">[14]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1">Ethyl Acetate</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-DeGreef1">[13]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1">Formic acid, ethenyl ester</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Hexadecanoic acid, ethyl ester</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Hexanoic acid, butyl ester</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Oxalic acid, hexyl propyl ester</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Propanoate, 2-hexen-1-ol</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Propanoic acid, 2-hydroxy-2-methyl-, ethyl ester</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Propanoic acid, 2-hydroxy-2-methyl-, methyl ester</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Propanoic acid, 2-methyl-, butyl ester</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Propanoic acid, butyl ester</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Vinyl butyrate</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1"><bold>Sulfur compounds</bold></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td></tr><tr><td align="left" rowspan="1" colspan="1">Benzenesulfonic acid, 4-hydroxy-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Dicyclohexyldisulphide</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Disulfide, dimethyl</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Statheropoulos1">[3]</xref>–<xref ref-type="bibr" rid="pone.0039005-Dent1">[5]</xref>, <xref ref-type="bibr" rid="pone.0039005-Statheropoulos2">[7]</xref>–<xref ref-type="bibr" rid="pone.0039005-Hdrich1">[17]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1">Dothiepin</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Methane, sulfonylbis-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Sulfone, butyl isopropyl</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Sulfurous acid, dicyclohexyl ester</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Trisulfide, dimethyl</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Statheropoulos1">[3]</xref>–<xref ref-type="bibr" rid="pone.0039005-Dent1">[5]</xref>, <xref ref-type="bibr" rid="pone.0039005-Statheropoulos2">[7]</xref>–<xref ref-type="bibr" rid="pone.0039005-Statheropoulos4">[11]</xref>, <xref ref-type="bibr" rid="pone.0039005-DeGreef1">[13]</xref>–<xref ref-type="bibr" rid="pone.0039005-Kalinova1">[16]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1"><bold>Nitrogen compounds</bold></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td></tr><tr><td align="left" rowspan="1" colspan="1">1-Butanamine, 3-methyl-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">1-Butanol, 4-Amino-</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">1-Decanamine</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">1-Heptadecanamine</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">2-Piperidinone</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Dekeirsschieter1">[14]</xref>–<xref ref-type="bibr" rid="pone.0039005-Akdeniz1">[15]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1">2-Propanol, 1-amino-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">2,3-Butanediol, dinitrate</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">2,3-Dihydrooxazole, 2-t-butyl-4-(1-hydroxy-1-methylethyl)-3-methoxycarbonyl-5-methyl-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">5,5-Dimethylimidazolidin-2,4-diimine</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Acetamide</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Dekeirsschieter1">[14]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1">Acetamide, N-methyl-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Dekeirsschieter1">[14]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1">Acetamide, N,N-dimethyl-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Vass4">[9]</xref>, <xref ref-type="bibr" rid="pone.0039005-Dekeirsschieter1">[14]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1">Acetic acid, [(aminocarbonyl)amino]oxo-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Benzaldehyde, 2-amino-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Butanamide</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Dekeirsschieter1">[14]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1">Butanamide, 3-methyl-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Dekeirsschieter1">[14]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1">Formamide, (2-acetylphenyl)-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Formamide, N-(2-methylpropyl)-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Formamide, N-butyl-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Formamide, N-methyl-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Formamide, N-phenyl-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Formamide, N,N-dimethyl-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Statheropoulos2">[7]</xref>, <xref ref-type="bibr" rid="pone.0039005-Dekeirsschieter1">[14]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1">Heptanonitrile</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Hexanamide</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Hexanamide, N-methyl</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Methanamine, N,N-dimethyl-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Methanediamine, N,N,N',N'-tetramethyl-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-DeGreef1">[13]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1">N-Methylvaleramide</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Pentanamide</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Propanamide</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Dekeirsschieter1">[14]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1">Propanamide, 2-methyl-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Propanamide, N-methyl-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Dekeirsschieter1">[14]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1">Propanamide, N,2-dimethyl-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Propanenitrile, 3-dimethylamino-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Propylamine</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Propylamine, N,N,2,2-tetramethyl-, N-oxide</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Trimethylamine</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Packowski1">[4]</xref>, <xref ref-type="bibr" rid="pone.0039005-Statheropoulos2">[7]</xref>, <xref ref-type="bibr" rid="pone.0039005-DeGreef1">[13]</xref>–<xref ref-type="bibr" rid="pone.0039005-Dekeirsschieter1">[14]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1"><bold>Aldehydes</bold></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td></tr><tr><td align="left" rowspan="1" colspan="1">2-Butenal, 3-methyl-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">2-Octenal</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Hoffman1">[12]</xref>–<xref ref-type="bibr" rid="pone.0039005-DeGreef1">[13]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1">Acetaldehyde</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Statheropoulos1">[3]</xref>, <xref ref-type="bibr" rid="pone.0039005-Hdrich1">[17]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1">Benzaldehyde</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Statheropoulos1">[3]</xref>–<xref ref-type="bibr" rid="pone.0039005-Packowski1">[4]</xref>, <xref ref-type="bibr" rid="pone.0039005-Statheropoulos2">[7]</xref>–<xref ref-type="bibr" rid="pone.0039005-Vass3">[8]</xref>, <xref ref-type="bibr" rid="pone.0039005-Hoffman1">[12]</xref>–<xref ref-type="bibr" rid="pone.0039005-Dekeirsschieter1">[14]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1">Heptanal</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Vass2">[2]</xref>, <xref ref-type="bibr" rid="pone.0039005-Packowski1">[4]</xref>, <xref ref-type="bibr" rid="pone.0039005-Vass4">[9]</xref>, <xref ref-type="bibr" rid="pone.0039005-Hoffman1">[12]</xref>–<xref ref-type="bibr" rid="pone.0039005-Dekeirsschieter1">[14]</xref>, <xref ref-type="bibr" rid="pone.0039005-Prada1">[59]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1">Hexanal</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Statheropoulos1">[3]</xref>–<xref ref-type="bibr" rid="pone.0039005-Packowski1">[4]</xref>, <xref ref-type="bibr" rid="pone.0039005-Statheropoulos3">[10]</xref>, <xref ref-type="bibr" rid="pone.0039005-Hoffman1">[12]</xref>–<xref ref-type="bibr" rid="pone.0039005-DeGreef1">[13]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1">Methylglyoxal</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Nonanal</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Packowski1">[4]</xref>, <xref ref-type="bibr" rid="pone.0039005-Vass3">[8]</xref>–<xref ref-type="bibr" rid="pone.0039005-Vass4">[9]</xref>, <xref ref-type="bibr" rid="pone.0039005-Hoffman1">[12]</xref>–<xref ref-type="bibr" rid="pone.0039005-DeGreef1">[13]</xref>, <xref ref-type="bibr" rid="pone.0039005-Hdrich1">[17]</xref>, <xref ref-type="bibr" rid="pone.0039005-Prada1">[59]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1">Nonenal</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Octanal</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Hoffman1">[12]</xref>–<xref ref-type="bibr" rid="pone.0039005-DeGreef1">[13]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1">Pentanal, 2-methyl-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Propanal</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Propanal, 2-hydroxy-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Propanal, 2,2-dimethyl-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1"><bold>Ketones</bold></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td></tr><tr><td align="left" rowspan="1" colspan="1">1-Octen-3-one</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">2-Cyclohexen-1-one, 3-methyl-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">2-Decanone</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Akdeniz1">[15]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1">2-Heptanone</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Statheropoulos1">[3]</xref>–<xref ref-type="bibr" rid="pone.0039005-Packowski1">[4]</xref>, <xref ref-type="bibr" rid="pone.0039005-Hoffman1">[12]</xref>–<xref ref-type="bibr" rid="pone.0039005-Dekeirsschieter1">[14]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1">2-Hexanone</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Statheropoulos1">[3]</xref>, <xref ref-type="bibr" rid="pone.0039005-Statheropoulos3">[10]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1">2-Nonanone</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Vass1">[1]</xref>, <xref ref-type="bibr" rid="pone.0039005-Packowski1">[4]</xref>, <xref ref-type="bibr" rid="pone.0039005-Vass4">[9]</xref>, <xref ref-type="bibr" rid="pone.0039005-Statheropoulos4">[11]</xref>, <xref ref-type="bibr" rid="pone.0039005-DeGreef1">[13]</xref>–<xref ref-type="bibr" rid="pone.0039005-Akdeniz1">[15]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1">2-Octanone</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Akdeniz1">[15]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1">2-Propanone, 1-phenyl-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">2-Undecanone</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">2,3-Octadione</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">2,4,6-Cycloheptatrien-1-one</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">2,5-Cyclohexadiene-1,4-dione</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">2,5-Hexanedione</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">2(3H)-Furanone, 5-butyldihydro- 2</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">2(3H)-Furanone, dihydro-5-methyl-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">3-Hexanone</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">3-Hexanone, 2-hydroxy-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">3-Octanone</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">3-Pentanone, 2-hydroxy</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">3-Penten-2-one, 4-methyl-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">4-Penten-2-one, 4-methyl-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">5-Hepten-2-one, 6-methyl</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-DeGreef1">[13]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1">Ç-Valerolactone</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Cyclohept-4-enone</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Cyclohexanone</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Statheropoulos1">[3]</xref>–<xref ref-type="bibr" rid="pone.0039005-Packowski1">[4]</xref>, <xref ref-type="bibr" rid="pone.0039005-Statheropoulos2">[7]</xref>, <xref ref-type="bibr" rid="pone.0039005-Hoffman1">[12]</xref>–<xref ref-type="bibr" rid="pone.0039005-DeGreef1">[13]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1">Cyclopentanone</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Cyclopentanone, 2-(1-methylpropyl)-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Ethanone, 1-phenyl-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1"><xref ref-type="bibr" rid="pone.0039005-Vass1">[1]</xref>, <xref ref-type="bibr" rid="pone.0039005-Statheropoulos4">[11]</xref>, <xref ref-type="bibr" rid="pone.0039005-DeGreef1">[13]</xref>–<xref ref-type="bibr" rid="pone.0039005-Dekeirsschieter1">[14]</xref></td></tr><tr><td align="left" rowspan="1" colspan="1">exo-5-Methyl-2-oxabicyclo[4.1.0]heptan-3-one</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Tridecan-2-one, 10-Methyl</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1"><bold>Ethers</bold></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td></tr><tr><td align="left" rowspan="1" colspan="1">1,3-Dioxolane, 2-acetyl-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">2-Propanol, 1-propoxy-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Ethene, methoxy-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Furan, 2-butyltetrahydro-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Furan, 2,3-dihydro-2,5-dimethyl-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Oxirane, 2,3-dimethyl-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Oxiranemethanol</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">halogen compounds</td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td></tr><tr><td align="left" rowspan="1" colspan="1">1-Chloroheptylacetate</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">1-Iodo-2-methylundecane</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Acetamidine, hydrochloride-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Butane, 1-bromo-2-methyl-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Propane, 1-bromo-2-methyl-</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1"><bold>Other compounds</bold></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td><td align="left" rowspan="1" colspan="1"></td></tr><tr><td align="left" rowspan="1" colspan="1">Butyl isocyanatoacetate</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Cyanic acid, 2-methylpropyl ester</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Cyanic acid, propyl ester</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Hydroperoxide, 1-ethylbutyl</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Hydroperoxide, 1-methylbutyl</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr><tr><td align="left" rowspan="1" colspan="1">Hydroperoxide, 1-methylpentyl</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">–</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">▴</td><td align="left" rowspan="1" colspan="1">N.R.</td></tr></tbody></table></alternatives><table-wrap-foot><fn id="nt102"><label></label><p>(▴) indicated a VOC detected or (-) for a VOC not detected. The column “literature report” lists the VOCs referenced in peer-reviewed literature (number correspond to the different papers concerning the decompositional chemistry and are listed in “References” section or not referenced (N.R.).</p></fn></table-wrap-foot></table-wrap></sec><sec id="s2b"><title>2. Volatile Collection</title><p>A dynamic sampling technique was used to collect volatile organic compounds released by the decaying pig carcass. The VOCs were collected in the headspace of the decaying pig with a pump device for 1 hour at 1 Lmin<sup>−1</sup> every two days during the field experiment. Simultaneously to the cadaveric VOC collection, air samples were collected as blank references. VOCs were trapped on cartridges, constituted of glass and Teflon®, containing a 40 µg SuperQ® adsorbent filter (80–100 mesh, Alltech Associates, Inc. Deerfield, IL, USA). The sorbent cartridge was connected to the pump device with Teflon® tubing and a glass funnel. The air sampling device (funnel and the sorbent cartridge) was disposed close to the abdominal cavity of the carcass (±3 cm).In the laboratory, VOCs were solvent eluted from the SuperQ® adsorbent with 150 µl of diethyl ether (HPLC grade, Sigma-Aldrich SA, Bornem, Belgium) and capped in GC-type vials. Before chromatographic analyses, liquid volatile samples were conserved at −80°C.</p></sec><sec id="s2c"><title>3. Chemicals</title><p>All solvents were Pestanal reagents (Riedel-de Haën, Seelze, Germany). Liquid nitrogen was purchased from Air Liquide (Liege, Belgium). Chromatographic pure grade helium gas, 99.9999%, was purchased from Air Products (Vilvoorde, Belgium).</p></sec><sec id="s2d"><title>4. Measurement by GCxGC-TOFMS</title><p>The GCxGC-TOFMS instrument was the Pegasus 4D (LECO Corp., St Joseph, MI, USA). This system is based on a non-moving quad-jet modulator consisting of two permanent cold nitrogen jets and two pulsed hot-air jets, which are responsible for the trapping and refocusing of compounds eluting from the first dimension (<sup>1</sup>D) column. This modulator was mounted in an Agilent 7890 GC oven and liquid nitrogen was used to create the cold jets. The column set was made of a 30 m Rtx®-5 (0.18 mm ID×0.20 µm df) (Restek Corp., Bellefonte, PA, USA) in the first dimension (<sup>1</sup>D) and a 1.0 m Rxi®-17 (0.10 mm ID×0.08 µm df) (SGE, Austin, TX, USA) in the second dimension (<sup>2</sup>D). The two columns were connected using a universal glass press tight connector (Restek Corp.). The modulation period (P<sub>M</sub>) was 4 s. The hot pulse duration was 600 ms. Helium was used as the carrier gas at a constant flow rate of 1 ml/min. 1 µl of the final extract in diethyl ether was injected into a split/splitless injector held at 200°C in splitless mode and equipped with a Double Gooseneck Restek liner. The primary oven was programmed as follows: 40°C for 5 min, at 5°C/min to 220°C and held for 5 min. The secondary oven temperature offset was 5°C, with a parallel temperature program. The modulator temperature offset was 10°C. The MS transfer line temperature was 225°C. A solvent delay of 300 seconds was used. The ion source temperature was 250°C with an electron impact (EI) energy of 70 eV. The collected mass range was 35–600 amu. The acquisition rate was 100 scans per second and the detector voltage was 1500 V.</p></sec><sec id="s2e"><title>5. Data Processing</title><p>Data processing and display of the GCxGC chromatograms were achieved using the integrated LECO ChromaTOF™ software, version 4.33. Peak apexes of deconvoluted signals were found automatically and were further corrected manually when required. The <sup>2</sup>D chromatographic peaks were recombined based on their second dimension retention time (<sup>2</sup>t<sub>R</sub>) and mass spectral similarity. Mass spectral data (DIC) were compared to the Wiley (2008) and the NIST (2008) libraries for temptative identification (similarity >700 and reverse match >900). Moreover, the area of each peak was calculated based on the apex mass reconstruction trace to increase the specificity during the comparison. All sample-blank couples were analyzed using the “Reference” option of the software to compare every sample to its blank. This part of the software is based on an algorithmic comparison of the data sets <xref ref-type="bibr" rid="pone.0039005-Leco1">[51]</xref>. To analyze one sample-blank couple, the comparison is based on both <sup>1</sup>t<sub>R</sub> and <sup>2</sup>t<sub>R</sub>, as well as the respective area and mass spectra data of each peak. The main comparison parameters were fixed at a tolerable shift of 8 seconds on <sup>1</sup>t<sub>R</sub> (twice P<sub>M</sub> value) and 0.2 seconds on <sup>2</sup>t<sub>R</sub>, and a tolerance of 50% absolute variation on the area. Following this comparison exercise, every single peak was categorized in one of the following groups: match (the compound is found in both injections), not found (the compound is only present in the sample), out of tolerance (the compound is present in both injections but at a different concentration level), and unknown (the compound is only present in the blank). The compounds sorted in the “not found” and “out of tolerance” (with a concentration under 10%) groups were classified as specific to the decomposition process.</p></sec><sec id="s2f"><title>6. Decomposition Stages</title><p>The decomposition process was observed according to different stages. We decided to discriminate five major decompositional stages based on different visual criteria adapted from the literature <xref ref-type="bibr" rid="pone.0039005-Campobasso1">[50]</xref>, <xref ref-type="bibr" rid="pone.0039005-Gennard1">[52]</xref>–<xref ref-type="bibr" rid="pone.0039005-Goff1">[58]</xref>: (1) fresh, (2) bloated, (3) active decay, (4) advanced decay and (5) dry remains. The decay stages are presented in <xref ref-type="table" rid="pone-0039005-t001">Table 1</xref>.</p></sec><sec id="s2g"><title>7. Statistical Analysis</title><p>In order to analyze the spatial distribution of our data set, a statistical analysis was conducted through multivariate principal component analysis (PCA) (Minitab® v15.1, State College, PA, USA). The original data set is a matrix of c×n (c = objects, n = variables) corresponding to a matrix of 12×225. Chemical compounds emitted only once were excluded from the multivariate analysis. The relative area of the chromatogram's peak corresponding to VOC was used for the multivariate analysis.</p></sec></sec><sec id="s3"><title>Results</title><sec id="s3a"><title>1. Environmental Parameters</title><p>The mean atmospheric temperature measured during the decay process was 13.1°C. <xref ref-type="fig" rid="pone-0039005-g001">Figure 1</xref> shows the temperature recordings in the forest site. The mean atmospheric maximal temperature was 20.2°C whereas the mean atmospheric minimal temperature was 6.7°C. The mean relative humidity was 68.3%. Local atmospheric temperature and relative humidity values were different to seasonal averages reported for the last 20 years by the royal Belgian meteorological institute (KMI-IRM). Mean atmospheric temperature from the Belgian KMI-IRM archives for spring 2007 (March to May) was 12.3°C (14.3°C for April and 14.6 for May 2007) whereas seasonal average was 9.5°C (9°C for April and 12.7°c for May). The maximal mean temperature from the Belgian KMI-IRM archives, for April 2007, was 20.5°C and 19°C for May. The minimal mean temperature from the Belgian KMI-IRM archives was 7.6°C for April 2007 and 10.3°C for May. The seasonal average for maximal temperature was 13.1°C for April and 17.2°C for May. For minimal temperature, the seasonal average was 5°C for April and 8.3°C for May. Spring 2007 was the warmest season since 100 years. Mean relative humidity from the Belgian KMI-IRM archives was 62% for April 2007 and 75% for May whereas seasonal averages were respectively 76.6% and 75.5%. Moreover, there was no day of precipitations during April 2007.</p></sec><sec id="s3b"><title>2. Decay Stages</title><p><xref ref-type="fig" rid="pone-0039005-g002">Figure 2</xref> illustrates the decay stages followed by the swine carcass in the forest biotope. The “fresh” stage began the day of the death (March 29, 2007) until 2<sup>nd</sup> of April, <italic>i.e.</italic> five postmortem days. The “bloating” stage began on the 3<sup>rd</sup> of April and finished on the 17<sup>th</sup> of April, the duration of the bloating stage was fifteen days. The “active decay” stage began on the 18<sup>th</sup> of April until the 30<sup>th</sup> of April. The duration of the active decay stage was thirteen days. The “advanced decay” stage began on the 1<sup>st</sup> of May until the 11<sup>th</sup> of May; this decomposition stage had duration of eleven days. The decay process was followed during six postmortem weeks.</p></sec><sec id="s3c"><title>3. Two-dimensional Chromatographic Screening</title><p><xref ref-type="fig" rid="pone-0039005-g003">Figure 3</xref> shows the GCxGC apex plot of a sample (1<sup>st</sup> of May) of the advanced decay stage. <xref ref-type="fig" rid="pone-0039005-g003">Figure 3A</xref> clearly illustrates the added value of GCxGC for such analyses for which classical GC would suffer from repeated co-elution issues (same <sup>1</sup>t<sub>R</sub>). After processing, the peak table of this chromatogram contained 633 hits. Hits included in the circled region could easily and repeatably be attributed to the extraction solvent. Hits included in the rectangle region were related to column bleed. After further removal of the hits present in the reference samples, 218 peaks were isolated (<xref ref-type="fig" rid="pone-0039005-g003">Figure 3B</xref>). Amongst these peaks, 42 were specifically found with at least 4 occurrences in other sample extracts (e.g. part of the 60 compounds listed in <xref ref-type="table" rid="pone-0039005-t002">Table 2</xref>, see next paragraph). <xref ref-type="fig" rid="pone-0039005-g003">Figure 3C</xref> illustrates their distribution over the chromatographic space. All samples were processed the same way before compilation of the list of specific compounds.</p></sec><sec id="s3d"><title>4. Cadaveric Volatile Organic Compounds</title><p>More than 4,000 hits were reported from extract analyses. After clean-up of the lists from compounds present in reference soils, as well as from GC column bleed related and potential peak artifacts, a list of 830 VOCs specifically released under the pig decomposition process was extracted by GCxGC-TOFMS. Almost all chemical families of VOCs were represented (in parentheses, the number of chemical compounds identified): alkanes (<italic>i.e.</italic> saturated hydrocarbons) (82), alkenes (<italic>i.e</italic>. unsaturated hydrocarbons) (50), alcohols (64), carboxylic acids (45), aromatic compounds (84), esters (87), sulfur compounds (31), nitrogen compounds (141), aldehydes (32), ketones (110), halogen compounds (42), ethers (32) and unclassed compounds (30). <xref ref-type="table" rid="pone-0039005-t003">Table 3</xref> presents the 225 cadaveric VOCs which have at least two occurrences during the decay process; 605 chemical compounds were detected only once. Among these 225 chemical compounds, 1H-indole was the compound with the highest occurrence (eight occurrences), followed by five compounds with seven occurrences (2-methyl-1-pentene; 1,2,3-propanetriol; ethanol; 4-methylphenol and acetaldehyde). Ten compounds were found 6 times, for example: 1-butanol, butanoic acid, 2-methylpropanoic acid, DMDS (<italic>i.e</italic>. dimethyldisulfide) and DMTS (<italic>i.e.</italic> dimethyltrisulfide), 1-amino-2-propanol, N-butylformamide and N,N-formamide. Sixteen compounds had five occurrences, for instance: 2- and 3-methylbutanoic acid, pentanoic acid, trimethylamine, 2-octanone and 2-undecanone, nonanal. An exhaustive list of compound occurrences (only the chemical volatiles with four to eight occurrences) is compiled in <xref ref-type="table" rid="pone-0039005-t002">Table 2</xref>. <xref ref-type="fig" rid="pone-0039005-g004">Figure 4</xref> shows the number of cadaveric volatile chemicals released by sampling date. The highest number of postmortem compounds was monitored during the decay stages, more precisely during the active decay stage and early advanced decay stage. The active decay is the decompositional stage with the strongest olfactive signature as many chemicals were detected. On the contrary, few volatiles were detected during the fresh stage (one day postmortem time). Additionally, no decompositional odor was perceptible to the human sense of smell in the very early decompositional stages. The number of cadaveric VOCs increased with the course of time and decreased with the disappearance of soft tissues (advanced decay). The PCA diagram (<xref ref-type="fig" rid="pone-0039005-g005">Figure 5</xref>) shows the distribution of the postmortem time (dates) in a score-plot (F1, σ = 57.501; F2, σ = 26.086). The fresh and bloated stages are less differentiated from the decay stages. <xref ref-type="fig" rid="pone-0039005-g006">Figure 6</xref> shows the repartition of chemical families detected in the headspace of decaying swine carcass by postmortem time. The volatile pattern of decaying pig carcass changes over time. One day post-mortem (30<sup>th</sup> of March), alkene was the predominant chemical class with γ-terpinene and o-xylene. In the fresh decay stage (5 postmortem days), alcohol was the predominant chemical class with mainly 1-butanol. 8 postmortem days, the presence of alcohols decreased and ketones became the main chemical class with principally cyclohexanone (≈ 20% of the total of emitted volatiles) and 4-methyl-3-pent-2-one. Aldehydes (hexanal, pentadecanal, 2,2-dimethylpropanal, 3-methylbutanal, acetaldehyde) were also more abundant and represented approximately 15% of the total of emitted volatiles. Furthermore, in bloated stage, alcohols represent more than a third of the volatile emissions whereas carboxylic acids represented 35% with mainly one chemical compound (borinic acid, diethyl-). Nitrogen compounds became more important and represented moreover 10% of the total of volatile emissions. 15 postmortem days, aldehydes, aromatic and sulfur compounds were the main chemical classes. 2,2 dimethylpropanal was the predominant aldehyde and represented a third of the total of volatile emissions whereas 1H-indole (aromatic compound) represented approximately a quarter of the volatile emissions. With regards to sulfur compounds, dimethyltrisulfide (<italic>i.e.</italic> DMTS) and butyl isopropylsulfone were the predominant compounds detected. During the active decay stage, nitrogen compounds (1-butanol, 4-amino; trimethylamine) and sulfur compounds (DMTS ≈ 23% of the total of volatile emissions of 22 postmortem days) are the main chemical families. Butanoic acid (carboxylic acid) became more important in the volatile emissions. 26 postmortem days, 75% of the volatile emissions were carboxylic acids with 3-methylbutanoic acid (<italic>i.e</italic>. isovaleric acid), butanoic acid, 2-methylbutanoic acid, 2-methylpropanoic acid (<italic>i.e.</italic> isobutyric acid), 4-methylpentanoic acid (<italic>i.e.</italic> isocaproic acid). Many aromatic compounds (37 chemical compounds) were also detected on the 26 postmortem days, but the main compound was 4-methylphenol (<italic>i.e. p</italic>-cresol). 29 postmortem days, the main chemical class was still the carboxylic acids (butanoic acid, 2- and 3-methylbutanoic acid, 2-methylpropanoic acid) with moreover 80% of the total of volatile emissions. In the early advanced decay stage (33 to 36 postmortem days), the presence of carboxylic acids decreased and the predominant chemical classes were ketones and alkanes. Further in the advanced decay stage, the alkanes increased; the main saturated hydrocarbon was 1,3-diethylcyclopentane (≈50% of the total of volatile emissions of 36 postmortem days). Carboxylic acids, approximately 20% of the total of volatile emissions, were still present but to a lesser extent. 40 postmortem days, sulfur compounds were the predominant chemical class with 4-hydroxybenzenesulfonic acid and dimethyldisulfide (DMDS), which represented more than 60% of the volatile emissions. Aldehydes (mainly nonanal) and aromatic compounds (mainly 1H-indole) intervened respectively for 9% and 14% of the total of volatile emissions. Later in the advanced decay stage (43 postmortem days)), sulfur compounds (main compound: DMDS) decreased whereas ketones (2-hexanone, 3-hexanone and cyclohexanone), nitrogen compounds and carboxylic acid increased (2,3-dihydroxysuccinic acid).</p></sec></sec><sec id="s4"><title>Discussion</title><p>In previous study on swine decay chemistry (above ground decomposition in a forest biotope) <xref ref-type="bibr" rid="pone.0039005-Dekeirsschieter1">[14]</xref>, only 85 specific cadaveric volatiles were identified with conventional GC-MS whereas approximately ten times more compounds were detected with two-dimensional GCxGC-TOFMS (832 VOCs). Moreover, no cadaveric compounds were detected with conventional GC-quadrupole(q)MS during the first postmortem week (fresh decay and beginning of the bloated stages) <xref ref-type="bibr" rid="pone.0039005-Dekeirsschieter1">[14]</xref> whereas cadaveric volatiles were detected from the first postmortem day with bi-dimensional gas chromatography. This is most probably to be attributed to the enhanced chromatographic resolution and detectability of the zone-compressed peaks. <xref ref-type="fig" rid="pone-0039005-g003">Figure 3A</xref> also illustrates that separating column bleed and/or solvent related peaks in the second dimension contributes to better peak identification. Furthermore, the use of the chromatographic space rather than a classical chromatographic temporal line allows classes of compounds to be separated from each other (<xref ref-type="fig" rid="pone-0039005-g003">Figure 3C</xref>). Amides, aromatics, carboxylic acids exhibit different retention behaviors towards the <sup>2</sup>D GC phase. The availability of two t<sub>R</sub> values is an additional piece of information to potentially identify compounds with lower similarity values versus library spectra. The separation could still be improved for alcohols, ketones, carboxylic acids, and aldehydes, but the current situation is clearly improved compared to a situation where all peaks would be present on the top of each other on the x-axis of the chromatogram. For now, the deconvolution software of the TOFMS system can separate them for individual identification.</p><p>Other studies on the swine cadaveric decompositional process <xref ref-type="bibr" rid="pone.0039005-Statheropoulos2">[7]</xref>, <xref ref-type="bibr" rid="pone.0039005-Dekeirsschieter1">[14]</xref> or human decay <xref ref-type="bibr" rid="pone.0039005-Statheropoulos2">[7]</xref>–<xref ref-type="bibr" rid="pone.0039005-Hoffman1">[12]</xref> used GC-qMS <xref ref-type="bibr" rid="pone.0039005-Statheropoulos2">[7]</xref>–<xref ref-type="bibr" rid="pone.0039005-DeGreef1">[13]</xref>, <xref ref-type="bibr" rid="pone.0039005-Akdeniz1">[15]</xref>, <xref ref-type="bibr" rid="pone.0039005-Hdrich1">[17]</xref> or GC-TOFMS <xref ref-type="bibr" rid="pone.0039005-Statheropoulos2">[7]</xref> to analyze the decompositional odor. However, fewer cadaveric compounds were detected with GC-MS or GC-TOFMS than the two-dimensional gas chromatography. For example, in the Decompositional Odor Analysis Database (DOA Database), 478 specific volatile compounds associated with buried human remains were recovered <xref ref-type="bibr" rid="pone.0039005-Vass3">[8]</xref>–<xref ref-type="bibr" rid="pone.0039005-Vass4">[9]</xref> whereas Statheropoulos and colleagues <xref ref-type="bibr" rid="pone.0039005-Statheropoulos1">[3]</xref> detected more than 80 VOCs on putrefied human remains and 150 VOCs were identified on pig carcasses closed in a “body bag” during the early stages of decay <xref ref-type="bibr" rid="pone.0039005-Statheropoulos2">[7]</xref>. The volatile profiles of different types of human remain (blood, bones, adipose, teeth, skin, body fat, <italic>etc</italic>.), placed in small sealed vials, were constituted of 33 specific VOCs <xref ref-type="bibr" rid="pone.0039005-Hoffman1">[12]</xref>.</p><p>A recent study <xref ref-type="bibr" rid="pone.0039005-Kalinova1">[16]</xref> used the two dimensional GCxGC-TOFMS analysis to study the chemical composition of volatiles emanating from fresh laboratory mouse carcasses during the early decay stages. A fresh killed mouse (0–30 min old) emits the same volatile pattern as a living mouse. As the decay progresses, only sulfur compounds (S-VOCs) were detected during the first three days of postmortem time. In older mice carcasses, other decompositional by-products were identified such as aromatic phenolic compounds (indole, scatole), amines and mercaptoacetic acid <xref ref-type="bibr" rid="pone.0039005-Kalinova1">[16]</xref>. However, the olfactive signature of decaying mouse carcasses was not completely described and, except for S-VOCs, few cadaveric compounds were referenced in Kalinova and colleagues’ <xref ref-type="bibr" rid="pone.0039005-Kalinova1">[16]</xref> study. Again, their volatile samplings on mouse models were made in a small closed environment with solid-phase microextraction (SPME) during the beginning of the decompositional process, which may explain the differences. Indeed, postmortem volatiles may be concentrated in closed environments and are detectable earlier.</p><p>There is a large discrepancy in decomposition odor compounds reported in the literature <xref ref-type="bibr" rid="pone.0039005-DeGreef1">[13]</xref>. This difference could be explained by the various analytical protocols, including volatile extractions (sampling techniques and sorbent materials) and analytical separations, used to study the postmortem volatiles of vertebrate tissues <xref ref-type="bibr" rid="pone.0039005-Packowski1">[4]</xref>, <xref ref-type="bibr" rid="pone.0039005-Prada1">[59]</xref>. Moreover, the result of volatile analysis from decomposition of mammalian soft tissues is also influenced by abiotic factors such as temperature and moisture <xref ref-type="bibr" rid="pone.0039005-Packowski1">[4]</xref>. The use of different mammalian models or remains (tissues samples <italic>vs.</italic> whole corpses) could also lead to differences in cadaveric volatile profiles. There are some recommendations to examine the potential differences between human and animal models <xref ref-type="bibr" rid="pone.0039005-Swann1">[25]</xref>. Indeed, the olfactive signature of decaying pig carcasses shows similarities with the smell of human decomposition in terms of released chemical compounds <xref ref-type="bibr" rid="pone.0039005-DeGreef1">[13]</xref>–<xref ref-type="bibr" rid="pone.0039005-Dekeirsschieter1">[14]</xref>, but also dissimilarities <xref ref-type="bibr" rid="pone.0039005-DeGreef1">[13]</xref>. Recent research in this field indicated that the odor from human remains is different from that of animals <xref ref-type="bibr" rid="pone.0039005-DeGreef1">[13]</xref>. Two compounds were exclusively found on human remains and not on animal samples: styrene and benzoic acid methyl ester <xref ref-type="bibr" rid="pone.0039005-DeGreef1">[13]</xref>. These two compounds were not detected in our pig decaying samples. However, the principal identified cadaveric VOCs are, in general, in agreement with previous studies conducted on pig decaying carcasses <xref ref-type="bibr" rid="pone.0039005-Statheropoulos2">[7]</xref>, <xref ref-type="bibr" rid="pone.0039005-Dekeirsschieter1">[14]</xref>–<xref ref-type="bibr" rid="pone.0039005-Akdeniz1">[15]</xref>. These cadaveric compounds come from the chemical breakdown of the principal body constituents: proteins, lipids, nucleic acid and carbohydrates <xref ref-type="bibr" rid="pone.0039005-Vass2">[2]</xref>–<xref ref-type="bibr" rid="pone.0039005-Statheropoulos1">[3]</xref>, <xref ref-type="bibr" rid="pone.0039005-Swann1">[25]</xref>. Indole and other phenolic compounds (<italic>e.g</italic>. <italic>p</italic>-cresol) might originate from protein and fat decomposition <xref ref-type="bibr" rid="pone.0039005-Vass1">[1]</xref>, <xref ref-type="bibr" rid="pone.0039005-Statheropoulos2">[7]</xref>. Indeed, proteolysis (<italic>i.e.</italic> the breakdown of proteins by the action of bacterial enzymes <xref ref-type="bibr" rid="pone.0039005-Dent1">[5]</xref>, <xref ref-type="bibr" rid="pone.0039005-Evans1">[60]</xref>) yields gases, diamines (cadaverine, putrescine), sulfur compounds and phenolic compounds including indole and skatole <xref ref-type="bibr" rid="pone.0039005-Vass1">[1]</xref>, <xref ref-type="bibr" rid="pone.0039005-Statheropoulos1">[3]</xref>, <xref ref-type="bibr" rid="pone.0039005-Dent1">[5]</xref>, <xref ref-type="bibr" rid="pone.0039005-Evans1">[60]</xref>–<xref ref-type="bibr" rid="pone.0039005-Vass5">[61]</xref>.</p><p>Skatole (<italic>i.e.</italic> 3-methylindole) was not detected in the present study, confirming the findings of the previous study <xref ref-type="bibr" rid="pone.0039005-Dekeirsschieter1">[14]</xref>. In addition, cadaverine and putrescine were not detected as cadaveric VOCs in this study. The absence of these biogenic amines, usually associated with the decay process <xref ref-type="bibr" rid="pone.0039005-Vass2">[2]</xref>, <xref ref-type="bibr" rid="pone.0039005-GillKing1">[49]</xref>, is also confirmed in previous studies on volatile chemistry of human decay <xref ref-type="bibr" rid="pone.0039005-Statheropoulos1">[3]</xref>, <xref ref-type="bibr" rid="pone.0039005-Vass3">[8]</xref>–<xref ref-type="bibr" rid="pone.0039005-Vass4">[9]</xref> or swine decay <xref ref-type="bibr" rid="pone.0039005-Statheropoulos2">[7]</xref>, <xref ref-type="bibr" rid="pone.0039005-Dekeirsschieter1">[14]</xref>. Indeed, biogenic amines have a low volatility and therefore are not frequently identified with gas chromatography <xref ref-type="bibr" rid="pone.0039005-Packowski1">[4]</xref>. Liquid chromatography (LC) is more suitable to detect biogenic amines <xref ref-type="bibr" rid="pone.0039005-Packowski1">[4]</xref>. Even so, 2-piperidone, a cadaverine metabolite <xref ref-type="bibr" rid="pone.0039005-Callery1">[62]</xref>, was detected in our cadaveric emanation. Sulfur compounds such as DMDS and DMTS are very frequent biomarkers in cadaveric samples of vertebrate tissues <xref ref-type="bibr" rid="pone.0039005-Statheropoulos1">[3]</xref>–<xref ref-type="bibr" rid="pone.0039005-Dent1">[5]</xref>, <xref ref-type="bibr" rid="pone.0039005-Statheropoulos2">[7]</xref>–<xref ref-type="bibr" rid="pone.0039005-Hdrich1">[17]</xref>. Volatile sulfur compounds (VSCs or S-VOCs) come from the microbial breakdown of sulfur-containing amino acids (cysteine, methionine) <xref ref-type="bibr" rid="pone.0039005-Statheropoulos2">[7]</xref>. The oxygenated compounds (organic acids, alcohols <xref ref-type="bibr" rid="pone.0039005-Statheropoulos1">[3]</xref>, <xref ref-type="bibr" rid="pone.0039005-Dent1">[5]</xref>, <xref ref-type="bibr" rid="pone.0039005-GillKing1">[49]</xref>, ketones, aldehydes, esters and ethers <xref ref-type="bibr" rid="pone.0039005-Statheropoulos1">[3]</xref>) come from the carbohydrate decomposition. The breakdown of nucleic acids provides nitrogenous bases, phosphates and sugars <xref ref-type="bibr" rid="pone.0039005-Vass2">[2]</xref> whereas lipid degradation produces mainly fatty acids, hydrocarbons, oxygenated, phosphorus and nitrogen compounds <xref ref-type="bibr" rid="pone.0039005-Statheropoulos1">[3]</xref>, <xref ref-type="bibr" rid="pone.0039005-GillKing1">[49]</xref>. Nevertheless, it is important to remember that for some cadaveric compounds the pathways of their formation are not known in detail or are still completely unknown <xref ref-type="bibr" rid="pone.0039005-Packowski1">[4]</xref>, <xref ref-type="bibr" rid="pone.0039005-Statheropoulos2">[7]</xref>.</p><p>It is interesting to note that the dothiepin (also called dosulepin <xref ref-type="bibr" rid="pone.0039005-Chen1">[63]</xref>: 3-(dibenzo[b,e]thiepin-11(6H)-ylidene)-N,Ndimethylpropylamine <xref ref-type="bibr" rid="pone.0039005-Lambourn1">[64]</xref>–<xref ref-type="bibr" rid="pone.0039005-Keller1">[65]</xref>) was frequently found in our postmortem volatile samples. However, dothiepin is not a specific cadaveric VOC. Dothiepin is a tricyclic antidepressant with tranquilizing properties <xref ref-type="bibr" rid="pone.0039005-Chen1">[63]</xref>–<xref ref-type="bibr" rid="pone.0039005-Keller1">[65]</xref>. This compound was probably dosed antemortem to the pig by the veterinarian to improve the animal welfare. Indeed, psychotherapeutic drugs such as tricyclic antidepressants can be used to eliminate the anxiety-related behavior of animals <xref ref-type="bibr" rid="pone.0039005-Sorensen1">[66]</xref>. To the best of our knowledge, this is the first time that drug was detected on a decaying corpse with headspace collection and bi-dimensional gas chromatography. Nevertheless, some basic drugs, including dothiepin, could be detected in postmortem blood samples using gas chromatography coupled to mass spectrometry with ion trap detection <xref ref-type="bibr" rid="pone.0039005-Paterson1">[67]</xref>. The headspace detection of volatile compounds of forensic interest (<italic>e.g.</italic> drugs, ethanol) on decaying corpse opens up new possibilities in forensic toxicology. Recent research has been conducted into the development of direct headspace sampling methods to analyze volatile compounds of forensic interest in human biological fluids <xref ref-type="bibr" rid="pone.0039005-Kusano1">[68]</xref>–<xref ref-type="bibr" rid="pone.0039005-Kovatsi1">[69]</xref>.</p><p>In conclusion, this study provides the first documentation of the use of GCxGC-TOFMS to analyze pig decaying volatile compounds. The use of comprehensive GC could improve the characterization of the smell of death in terms of volatile constitution, rather than conventional GC. Indeed, the complexity of postmortem volatile samples requires more complex analytical methods <xref ref-type="bibr" rid="pone.0039005-Swann1">[25]</xref>. Concerning data analysis, it would be interesting to include chemometrics analysis in future work. Nevertheless, the solvent extraction of the volatile organic compounds from the sorbent cartridges as well as the storage of the liquid fraction prior analyses is not adequate for the most volatile polar compounds, compared to the use of thermal desorption techniques, which is currently under investigation. However, our results demonstrated that bi-dimensional gas chromatography coupled with time-of-flight mass spectrometry is a powerful tool to analyze the volatile cadaveric emissions.</p></sec></body><back><ack><p>Restek Corp. is acknowledged for providing GC columns and other chromatographic consumables. Yves Brostaux (Department of Applied Statistics, Computer Science and Mathematics, Gembloux Agro-Bio Tech, University of Liege) is acknowledged for his help in statistical data treatment.</p></ack><fn-group><fn fn-type="conflict"><p><bold>Competing Interests: </bold>The authors have declared that no competing interests exist.</p></fn><fn fn-type="financial-disclosure"><p><bold>Funding: </bold>Jessica Dekeirsschieter was financially supported by a PhD grant from the Fonds pour la formation à la Recherche dans l’Industrie et l’Agriculture (F.R.I.A.), Belgium. Catherine Brasseur and Pierre-Hugues Stefanuto were financially supported by a teaching assistant PhD grant from the Chemistry Department of the University of Liège. 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