Structure-odor relationships of linalool, linalyl acetate and their corresponding oxygenated derivatives
Identifieur interne : 000063 ( Pmc/Curation ); précédent : 000062; suivant : 000064Structure-odor relationships of linalool, linalyl acetate and their corresponding oxygenated derivatives
Auteurs : Shaimaa A. Elsharif [Allemagne] ; Ashutosh Banerjee [Allemagne] ; Andrea Buettner [Allemagne]Source :
- Frontiers in Chemistry [ 2296-2646 ] ; 2015.
Abstract
Linalool
Url:
DOI: 10.3389/fchem.2015.00057
PubMed: 26501053
PubMed Central: 4594031
Links toward previous steps (curation, corpus...)
- to stream Pmc, to step Corpus: Pour aller vers cette notice dans l'étape Curation :000063
Links to Exploration step
PMC:4594031Le document en format XML
<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Structure-odor relationships of linalool, linalyl acetate and their corresponding oxygenated derivatives</title><author><name sortKey="Elsharif, Shaimaa A" sort="Elsharif, Shaimaa A" uniqKey="Elsharif S" first="Shaimaa A." last="Elsharif">Shaimaa A. Elsharif</name><affiliation wicri:level="1"><nlm:aff id="aff1"><institution>Department of Chemistry and Pharmacy, Food Chemistry, Emil Fischer Center, Friedrich-Alexander-Universität Erlangen-Nürnberg</institution><country>Erlangen, Germany</country></nlm:aff><country xml:lang="fr">Allemagne</country><wicri:regionArea></wicri:regionArea></affiliation></author><author><name sortKey="Banerjee, Ashutosh" sort="Banerjee, Ashutosh" uniqKey="Banerjee A" first="Ashutosh" last="Banerjee">Ashutosh Banerjee</name><affiliation wicri:level="1"><nlm:aff id="aff2"><institution>Department of Chemistry and Pharmacy, Pharmaceutical Chemistry, Emil Fischer Center, Friedrich-Alexander-Universität Erlangen-Nürnberg</institution><country>Erlangen, Germany</country></nlm:aff><country xml:lang="fr">Allemagne</country><wicri:regionArea></wicri:regionArea></affiliation></author><author><name sortKey="Buettner, Andrea" sort="Buettner, Andrea" uniqKey="Buettner A" first="Andrea" last="Buettner">Andrea Buettner</name><affiliation wicri:level="1"><nlm:aff id="aff1"><institution>Department of Chemistry and Pharmacy, Food Chemistry, Emil Fischer Center, Friedrich-Alexander-Universität Erlangen-Nürnberg</institution><country>Erlangen, Germany</country></nlm:aff><country xml:lang="fr">Allemagne</country><wicri:regionArea></wicri:regionArea></affiliation><affiliation wicri:level="1"><nlm:aff id="aff3"><institution>Department of Sensory Analytics, Fraunhofer Institute for Process Engineering and Packaging</institution><country>Freising, Germany</country></nlm:aff><country xml:lang="fr">Allemagne</country><wicri:regionArea></wicri:regionArea></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PMC</idno><idno type="pmid">26501053</idno><idno type="pmc">4594031</idno><idno type="url">http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4594031</idno><idno type="RBID">PMC:4594031</idno><idno type="doi">10.3389/fchem.2015.00057</idno><date when="2015">2015</date><idno type="wicri:Area/Pmc/Corpus">000063</idno><idno type="wicri:Area/Pmc/Curation">000063</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">Structure-odor relationships of linalool, linalyl acetate and their corresponding oxygenated derivatives</title><author><name sortKey="Elsharif, Shaimaa A" sort="Elsharif, Shaimaa A" uniqKey="Elsharif S" first="Shaimaa A." last="Elsharif">Shaimaa A. Elsharif</name><affiliation wicri:level="1"><nlm:aff id="aff1"><institution>Department of Chemistry and Pharmacy, Food Chemistry, Emil Fischer Center, Friedrich-Alexander-Universität Erlangen-Nürnberg</institution><country>Erlangen, Germany</country></nlm:aff><country xml:lang="fr">Allemagne</country><wicri:regionArea></wicri:regionArea></affiliation></author><author><name sortKey="Banerjee, Ashutosh" sort="Banerjee, Ashutosh" uniqKey="Banerjee A" first="Ashutosh" last="Banerjee">Ashutosh Banerjee</name><affiliation wicri:level="1"><nlm:aff id="aff2"><institution>Department of Chemistry and Pharmacy, Pharmaceutical Chemistry, Emil Fischer Center, Friedrich-Alexander-Universität Erlangen-Nürnberg</institution><country>Erlangen, Germany</country></nlm:aff><country xml:lang="fr">Allemagne</country><wicri:regionArea></wicri:regionArea></affiliation></author><author><name sortKey="Buettner, Andrea" sort="Buettner, Andrea" uniqKey="Buettner A" first="Andrea" last="Buettner">Andrea Buettner</name><affiliation wicri:level="1"><nlm:aff id="aff1"><institution>Department of Chemistry and Pharmacy, Food Chemistry, Emil Fischer Center, Friedrich-Alexander-Universität Erlangen-Nürnberg</institution><country>Erlangen, Germany</country></nlm:aff><country xml:lang="fr">Allemagne</country><wicri:regionArea></wicri:regionArea></affiliation><affiliation wicri:level="1"><nlm:aff id="aff3"><institution>Department of Sensory Analytics, Fraunhofer Institute for Process Engineering and Packaging</institution><country>Freising, Germany</country></nlm:aff><country xml:lang="fr">Allemagne</country><wicri:regionArea></wicri:regionArea></affiliation></author></analytic><series><title level="j">Frontiers in Chemistry</title><idno type="eISSN">2296-2646</idno><imprint><date when="2015">2015</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><p>Linalool <bold>1</bold> is an odorant that is commonly perceived as having a pleasant odor, but is also known to elicit physiological effects such as inducing calmness and enhancing sleep. However, no comprehensive studies are at hand to show which structural features are responsible for these prominent effects. Therefore, a total of six oxygenated derivatives were synthesized from both <bold>1</bold> and linalyl acetate <bold>2</bold>, and were tested for their odor qualities and relative odor thresholds (OTs) in air. Linalool was found to be the most potent odorant among the investigated compounds, with an average OT of 3.2 ng/L, while the 8-hydroxylinalool derivative was the least odorous compound with an OT of 160 ng/L; 8-carboxylinalool was found to be odorless. The odorant 8-oxolinalyl acetate, which has very similar odor properties to linalool, was the most potent odorant besides linalool, exhibiting an OT of 5.9 ng/L. By comparison, 8-carboxylinalyl acetate had a similar OT (6.1 ng/L) as its corresponding 8-oxo derivative but exhibited divergent odor properties (<italic>fatty, greasy, musty</italic>). Overall, oxygenation on carbon 8 had a substantial effect on the aroma profiles of structural derivatives of linalool and linalyl acetate.</p></div></front><back><div1 type="bibliography"><listBibl><biblStruct><analytic><author><name sortKey="Andi, S A" uniqKey="Andi S">S. A. Andi</name></author><author><name sortKey="Nazeri, V" uniqKey="Nazeri V">V. Nazeri</name></author><author><name sortKey="Hadian, J" uniqKey="Hadian J">J. Hadian</name></author><author><name sortKey="Zamani, Z" uniqKey="Zamani Z">Z. Zamani</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Aprotosoaie, A C" uniqKey="Aprotosoaie A">A. C. Aprotosoaie</name></author><author><name sortKey="Hancianu, M" uniqKey="Hancianu M">M. Hãncianu</name></author><author><name sortKey="Costache, I I" uniqKey="Costache I">I.-I. Costache</name></author><author><name sortKey="Miron, A" uniqKey="Miron A">A. Miron</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Buchbauer, G" uniqKey="Buchbauer G">G. Buchbauer</name></author><author><name sortKey="Jirovetz, L" uniqKey="Jirovetz L">L. Jirovetz</name></author><author><name sortKey="J Ger, W" uniqKey="J Ger W">W. Jäger</name></author><author><name sortKey="Dietrich, H" uniqKey="Dietrich H">H. Dietrich</name></author><author><name sortKey="Plank, C" uniqKey="Plank C">C. Plank</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Cal, K" uniqKey="Cal K">K. Cal</name></author><author><name sortKey="Krzyzaniak, M" uniqKey="Krzyzaniak M">M. Krzyzaniak</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Chadha, A" uniqKey="Chadha A">A. Chadha</name></author><author><name sortKey="Madyastha, K M" uniqKey="Madyastha K">K. M. Madyastha</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Chantraine, J M" uniqKey="Chantraine J">J.-M. Chantraine</name></author><author><name sortKey="Dhenin, J M" uniqKey="Dhenin J">J.-M. Dhénin</name></author><author><name sortKey="Moretti, C" uniqKey="Moretti C">C. Moretti</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Chin, Y W" uniqKey="Chin Y">Y. W. Chin</name></author><author><name sortKey="Chai, H B" uniqKey="Chai H">H. B. Chai</name></author><author><name sortKey="Keller, W J" uniqKey="Keller W">W. J. Keller</name></author><author><name sortKey="Kinghorn, A D" uniqKey="Kinghorn A">A. D. Kinghorn</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Czerny, M" uniqKey="Czerny M">M. Czerny</name></author><author><name sortKey="Brueckner, R" uniqKey="Brueckner R">R. Brueckner</name></author><author><name sortKey="Kirchhoff, E" uniqKey="Kirchhoff E">E. Kirchhoff</name></author><author><name sortKey="Schmitt, R" uniqKey="Schmitt R">R. Schmitt</name></author><author><name sortKey="Buettner, A" uniqKey="Buettner A">A. Buettner</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Czerny, M" uniqKey="Czerny M">M. Czerny</name></author><author><name sortKey="Christlbauer, M" uniqKey="Christlbauer M">M. Christlbauer</name></author><author><name sortKey="Christlbauer, M" uniqKey="Christlbauer M">M. Christlbauer</name></author><author><name sortKey="Fischer, A" uniqKey="Fischer A">A. Fischer</name></author><author><name sortKey="Granvogl, M" uniqKey="Granvogl M">M. Granvogl</name></author><author><name sortKey="Hammer, M" uniqKey="Hammer M">M. Hammer</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="D Acampora Zellner, B" uniqKey="D Acampora Zellner B">B. d'Acampora Zellner</name></author><author><name sortKey="Casilli, A" uniqKey="Casilli A">A. Casilli</name></author><author><name sortKey="Dugo, P" uniqKey="Dugo P">P. Dugo</name></author><author><name sortKey="Dugo, G" uniqKey="Dugo G">G. Dugo</name></author><author><name sortKey="Mondello, L" uniqKey="Mondello L">L. Mondello</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Field, T" uniqKey="Field T">T. Field</name></author><author><name sortKey="Field, T" uniqKey="Field T">T. Field</name></author><author><name sortKey="Cullen, C" uniqKey="Cullen C">C. Cullen</name></author><author><name sortKey="Largie, S" uniqKey="Largie S">S. Largie</name></author><author><name sortKey="Diego, M" uniqKey="Diego M">M. Diego</name></author><author><name sortKey="Schanberg, S" uniqKey="Schanberg S">S. Schanberg</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Friedland, K" uniqKey="Friedland K">K. Friedland</name></author><author><name sortKey="Harteneck, C" uniqKey="Harteneck C">C. Harteneck</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Goel, N" uniqKey="Goel N">N. Goel</name></author><author><name sortKey="Kim, H" uniqKey="Kim H">H. Kim</name></author><author><name sortKey="Lao, R P" uniqKey="Lao R">R. P. Lao</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Hasegawa, T" uniqKey="Hasegawa T">T. Hasegawa</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Hudson, R" uniqKey="Hudson R">R. Hudson</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Kako, H" uniqKey="Kako H">H. Kako</name></author><author><name sortKey="Fukumoto, S" uniqKey="Fukumoto S">S. Fukumoto</name></author><author><name sortKey="Kobayashi, Y" uniqKey="Kobayashi Y">Y. Kobayashi</name></author><author><name sortKey="Yokogoshi, H" uniqKey="Yokogoshi H">H. Yokogoshi</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Kessler, A" uniqKey="Kessler A">A. Kessler</name></author><author><name sortKey="Sahin Nadeem, H" uniqKey="Sahin Nadeem H">H. Sahin-Nadeem</name></author><author><name sortKey="Lummis, S C" uniqKey="Lummis S">S. C. Lummis</name></author><author><name sortKey="Weigel, I" uniqKey="Weigel I">I. Weigel</name></author><author><name sortKey="Pischetsrieder, M" uniqKey="Pischetsrieder M">M. Pischetsrieder</name></author><author><name sortKey="Buettner, A" uniqKey="Buettner A">A. Buettner</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Kessler, A" uniqKey="Kessler A">A. Kessler</name></author><author><name sortKey="Villmann, C" uniqKey="Villmann C">C. Villmann</name></author><author><name sortKey="Sahin Nadeem, H" uniqKey="Sahin Nadeem H">H. Sahin-Nadeem</name></author><author><name sortKey="Pischetsrieder, M" uniqKey="Pischetsrieder M">M. Pischetsrieder</name></author><author><name sortKey="Buettner, A" uniqKey="Buettner A">A. Buettner</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Kiecolt Glaser, J K" uniqKey="Kiecolt Glaser J">J. K. Kiecolt-Glaser</name></author><author><name sortKey="Graham, J E" uniqKey="Graham J">J. E. Graham</name></author><author><name sortKey="Malarkey, W B" uniqKey="Malarkey W">W. B. Malarkey</name></author><author><name sortKey="Porter, K" uniqKey="Porter K">K. Porter</name></author><author><name sortKey="Lemeshow, S" uniqKey="Lemeshow S">S. Lemeshow</name></author><author><name sortKey="Glaser, R" uniqKey="Glaser R">R. Glaser</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="King, A J" uniqKey="King A">A. J. King</name></author><author><name sortKey="Dickinson, J R" uniqKey="Dickinson J">J. R. Dickinson</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Kreck, M" uniqKey="Kreck M">M. Kreck</name></author><author><name sortKey="Puschel, S" uniqKey="Puschel S">S. Püschel</name></author><author><name sortKey="Wust, M" uniqKey="Wust M">M. Wüst</name></author><author><name sortKey="Mosandl, A" uniqKey="Mosandl A">A. Mosandl</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Kremer, D" uniqKey="Kremer D">D. Kremer</name></author><author><name sortKey="Dunki, V" uniqKey="Dunki V">V. Dunkić</name></author><author><name sortKey="Rus I, M" uniqKey="Rus I M">M. Ruščić</name></author><author><name sortKey="Matevski, V" uniqKey="Matevski V">V. Matevski</name></author><author><name sortKey="Ballian, D" uniqKey="Ballian D">D. Ballian</name></author><author><name sortKey="Boguni, F" uniqKey="Boguni F">F. Bogunić</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Lahlou, M" uniqKey="Lahlou M">M. Lahlou</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Liu, H X" uniqKey="Liu H">H.-X. Liu</name></author><author><name sortKey="Chen, X H" uniqKey="Chen X">X.-H. Chen</name></author><author><name sortKey="Huang, C S" uniqKey="Huang C">C.-S. Huang</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Luan, F" uniqKey="Luan F">F. Luan</name></author><author><name sortKey="Mosandl, A" uniqKey="Mosandl A">A. Mosandl</name></author><author><name sortKey="Degenhardt, A" uniqKey="Degenhardt A">A. Degenhardt</name></author><author><name sortKey="Gubesch, M" uniqKey="Gubesch M">M. Gubesch</name></author><author><name sortKey="Wust, M" uniqKey="Wust M">M. Wüst</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Matsubara, Y" uniqKey="Matsubara Y">Y. Matsubara</name></author><author><name sortKey="Sawabe, A" uniqKey="Sawabe A">A. Sawabe</name></author><author><name sortKey="Iba, H" uniqKey="Iba H">H. Iba</name></author><author><name sortKey="Iizuka, Y" uniqKey="Iizuka Y">Y. Iizuka</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Miguel, M G" uniqKey="Miguel M">M. G. Miguel</name></author><author><name sortKey="Dandlen, S" uniqKey="Dandlen S">S. Dandlen</name></author><author><name sortKey="Figueiredo, A C" uniqKey="Figueiredo A">A. C. Figueiredo</name></author><author><name sortKey="Barroso, J G" uniqKey="Barroso J">J. G. Barroso</name></author><author><name sortKey="Pedro, L G" uniqKey="Pedro L">L. G. Pedro</name></author><author><name sortKey="Duarte, A" uniqKey="Duarte A">A. Duarte</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Mookherjee, B D" uniqKey="Mookherjee B">B. D. Mookherjee</name></author><author><name sortKey="Trenkle, R W" uniqKey="Trenkle R">R. W. Trenkle</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Omori, H" uniqKey="Omori H">H. Omori</name></author><author><name sortKey="Nakahara, K" uniqKey="Nakahara K">K. Nakahara</name></author><author><name sortKey="Umano, K" uniqKey="Umano K">K. Umano</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Ozek, T" uniqKey="Ozek T">T. Ozek</name></author><author><name sortKey="Tabanca, N" uniqKey="Tabanca N">N. Tabanca</name></author><author><name sortKey="Demirci, F" uniqKey="Demirci F">F. Demirci</name></author><author><name sortKey="Wedge, D E" uniqKey="Wedge D">D. E. Wedge</name></author><author><name sortKey="Baser, K H C" uniqKey="Baser K">K. H. C. Baser</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Pinnick, H W" uniqKey="Pinnick H">H. W. Pinnick</name></author><author><name sortKey="Bal, B S" uniqKey="Bal B">B. S. Bal</name></author><author><name sortKey="Childers, W E" uniqKey="Childers W">W. E. Childers</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Renganathan, V" uniqKey="Renganathan V">V. Renganathan</name></author><author><name sortKey="Madyastha, K M" uniqKey="Madyastha K">K. M. Madyastha</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Stashenko, E E" uniqKey="Stashenko E">E. E. Stashenko</name></author><author><name sortKey="Martinez, J R" uniqKey="Martinez J">J. R. Martínez</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Strauss, C R" uniqKey="Strauss C">C. R. Strauss</name></author><author><name sortKey="Wilson, B" uniqKey="Wilson B">B. Wilson</name></author><author><name sortKey="Williams, P J" uniqKey="Williams P">P. J. Williams</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Tasev, T" uniqKey="Tasev T">T. Tasev</name></author><author><name sortKey="Toleva, P" uniqKey="Toleva P">P. Toléva</name></author><author><name sortKey="Balabanova, V" uniqKey="Balabanova V">V. Balabanova</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Tsagkli, A" uniqKey="Tsagkli A">A. Tsagkli</name></author><author><name sortKey="Hancianu, M" uniqKey="Hancianu M">M. Hancianu</name></author><author><name sortKey="Aprotosoaie, C" uniqKey="Aprotosoaie C">C. Aprotosoaie</name></author><author><name sortKey="Cioanca, O" uniqKey="Cioanca O">O. Cioanca</name></author><author><name sortKey="Tzakou, O" uniqKey="Tzakou O">O. Tzakou</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Uchiyama, T" uniqKey="Uchiyama T">T. Uchiyama</name></author><author><name sortKey="Miyase, T" uniqKey="Miyase T">T. Miyase</name></author><author><name sortKey="Ueno, A" uniqKey="Ueno A">A. Ueno</name></author><author><name sortKey="Usmanghani, K" uniqKey="Usmanghani K">K. Usmanghani</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Ullrich, F" uniqKey="Ullrich F">F. Ullrich</name></author><author><name sortKey="Grosch, W" uniqKey="Grosch W">W. Grosch</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Van Den Dool, H" uniqKey="Van Den Dool H">H. Van Den Dool</name></author><author><name sortKey="Kratz, P D" uniqKey="Kratz P">P. D. Kratz</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Van Dort, H M" uniqKey="Van Dort H">H. M. Van Dort</name></author><author><name sortKey="Jagers, P P" uniqKey="Jagers P">P. P. Jagers</name></author><author><name sortKey="Ter Heide, R" uniqKey="Ter Heide R">R. Ter Heide</name></author><author><name sortKey="Van Der Weerdt, A J A" uniqKey="Van Der Weerdt A">A. J. A. Van Der Weerdt</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Wakayama, S" uniqKey="Wakayama S">S. Wakayama</name></author><author><name sortKey="Namba, S" uniqKey="Namba S">S. Namba</name></author><author><name sortKey="Hosoi, K" uniqKey="Hosoi K">K. Hosoi</name></author><author><name sortKey="Ohno, M" uniqKey="Ohno M">M. Ohno</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Yahagi, T" uniqKey="Yahagi T">T. Yahagi</name></author><author><name sortKey="Daikonya, A" uniqKey="Daikonya A">A. Daikonya</name></author><author><name sortKey="Kitanaka, S" uniqKey="Kitanaka S">S. Kitanaka</name></author></analytic></biblStruct></listBibl></div1></back></TEI><pmc article-type="research-article"><pmc-dir>properties open_access</pmc-dir>
<front><journal-meta><journal-id journal-id-type="nlm-ta">Front Chem</journal-id><journal-id journal-id-type="iso-abbrev">Front Chem</journal-id><journal-id journal-id-type="publisher-id">Front. Chem.</journal-id><journal-title-group><journal-title>Frontiers in Chemistry</journal-title></journal-title-group><issn pub-type="epub">2296-2646</issn><publisher><publisher-name>Frontiers Media S.A.</publisher-name></publisher></journal-meta><article-meta><article-id pub-id-type="pmid">26501053</article-id><article-id pub-id-type="pmc">4594031</article-id><article-id pub-id-type="doi">10.3389/fchem.2015.00057</article-id><article-categories><subj-group subj-group-type="heading"><subject>Nutrition</subject><subj-group><subject>Original Research</subject></subj-group></subj-group></article-categories><title-group><article-title>Structure-odor relationships of linalool, linalyl acetate and their corresponding oxygenated derivatives</article-title></title-group><contrib-group><contrib contrib-type="author"><name><surname>Elsharif</surname><given-names>Shaimaa A.</given-names></name><xref ref-type="aff" rid="aff1"><sup>1</sup></xref><uri xlink:type="simple" xlink:href="http://loop.frontiersin.org/people/261185/overview"></uri></contrib><contrib contrib-type="author"><name><surname>Banerjee</surname><given-names>Ashutosh</given-names></name><xref ref-type="aff" rid="aff2"><sup>2</sup></xref></contrib><contrib contrib-type="author"><name><surname>Buettner</surname><given-names>Andrea</given-names></name><xref ref-type="aff" rid="aff1"><sup>1</sup></xref><xref ref-type="aff" rid="aff3"><sup>3</sup></xref><xref ref-type="author-notes" rid="fn001"><sup>*</sup></xref><uri xlink:type="simple" xlink:href="http://loop.frontiersin.org/people/236351/overview"></uri></contrib></contrib-group><aff id="aff1"><sup>1</sup><institution>Department of Chemistry and Pharmacy, Food Chemistry, Emil Fischer Center, Friedrich-Alexander-Universität Erlangen-Nürnberg</institution><country>Erlangen, Germany</country></aff><aff id="aff2"><sup>2</sup><institution>Department of Chemistry and Pharmacy, Pharmaceutical Chemistry, Emil Fischer Center, Friedrich-Alexander-Universität Erlangen-Nürnberg</institution><country>Erlangen, Germany</country></aff><aff id="aff3"><sup>3</sup><institution>Department of Sensory Analytics, Fraunhofer Institute for Process Engineering and Packaging</institution><country>Freising, Germany</country></aff><author-notes><fn fn-type="edited-by"><p>Edited by: Dejian Huang, National University of Singapore, Singapore</p></fn><fn fn-type="edited-by"><p>Reviewed by: Muhammad Safder, University of Karachi, Pakistan; Marcin Szymanski, Poznan University of Medical Sciences, Poland</p></fn><corresp id="fn001">*Correspondence: Andrea Buettner, Erlangen, Germany <email xlink:type="simple">andrea.buettner@fau.de</email></corresp><fn fn-type="other" id="fn002"><p>This article was submitted to Food Chemistry, a section of the journal Frontiers in Chemistry</p></fn></author-notes><pub-date pub-type="epub"><day>06</day><month>10</month><year>2015</year></pub-date><pub-date pub-type="collection"><year>2015</year></pub-date><volume>3</volume><elocation-id>57</elocation-id><history><date date-type="received"><day>31</day><month>7</month><year>2015</year></date><date date-type="accepted"><day>14</day><month>9</month><year>2015</year></date></history><permissions><copyright-statement>Copyright © 2015 Elsharif, Banerjee and Buettner.</copyright-statement><copyright-year>2015</copyright-year><copyright-holder>Elsharif, Banerjee and Buettner</copyright-holder><license xlink:href="http://creativecommons.org/licenses/by/4.0/"><license-p>This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) or licensor are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.</license-p></license></permissions><abstract><p>Linalool <bold>1</bold> is an odorant that is commonly perceived as having a pleasant odor, but is also known to elicit physiological effects such as inducing calmness and enhancing sleep. However, no comprehensive studies are at hand to show which structural features are responsible for these prominent effects. Therefore, a total of six oxygenated derivatives were synthesized from both <bold>1</bold> and linalyl acetate <bold>2</bold>, and were tested for their odor qualities and relative odor thresholds (OTs) in air. Linalool was found to be the most potent odorant among the investigated compounds, with an average OT of 3.2 ng/L, while the 8-hydroxylinalool derivative was the least odorous compound with an OT of 160 ng/L; 8-carboxylinalool was found to be odorless. The odorant 8-oxolinalyl acetate, which has very similar odor properties to linalool, was the most potent odorant besides linalool, exhibiting an OT of 5.9 ng/L. By comparison, 8-carboxylinalyl acetate had a similar OT (6.1 ng/L) as its corresponding 8-oxo derivative but exhibited divergent odor properties (<italic>fatty, greasy, musty</italic>). Overall, oxygenation on carbon 8 had a substantial effect on the aroma profiles of structural derivatives of linalool and linalyl acetate.</p></abstract><kwd-group><kwd>Linalool</kwd><kwd>linalyl acetate</kwd><kwd>gas chromatography-olfactometry</kwd><kwd>odor threshold in air</kwd><kwd>8-oxolinalyl acetate</kwd><kwd>8-carboxylinalyl acetate</kwd><kwd>odor qualities</kwd><kwd>retention index</kwd></kwd-group><counts><fig-count count="4"></fig-count><table-count count="3"></table-count><equation-count count="0"></equation-count><ref-count count="42"></ref-count><page-count count="10"></page-count><word-count count="6485"></word-count></counts></article-meta></front></pmc></record>Pour manipuler ce document sous Unix (Dilib)
EXPLOR_STEP=$WICRI_ROOT/Wicri/Bois/explor/OrangerV1/Data/Pmc/Curation
HfdSelect -h $EXPLOR_STEP/biblio.hfd -nk 000063 | SxmlIndent | more
Ou
HfdSelect -h $EXPLOR_AREA/Data/Pmc/Curation/biblio.hfd -nk 000063 | SxmlIndent | more
Pour mettre un lien sur cette page dans le réseau Wicri
{{Explor lien
|wiki= Wicri/Bois
|area= OrangerV1
|flux= Pmc
|étape= Curation
|type= RBID
|clé= PMC:4594031
|texte= Structure-odor relationships of linalool, linalyl acetate and their corresponding oxygenated derivatives
}}
Pour générer des pages wiki
HfdIndexSelect -h $EXPLOR_AREA/Data/Pmc/Curation/RBID.i -Sk "pubmed:26501053" \
| HfdSelect -Kh $EXPLOR_AREA/Data/Pmc/Curation/biblio.hfd \
| NlmPubMed2Wicri -a OrangerV1
| This area was generated with Dilib version V0.6.25. |  |