Structure-odor relationships of linalool, linalyl acetate and their corresponding oxygenated derivatives
Identifieur interne : 000443 ( Main/Exploration ); précédent : 000442; suivant : 000444Structure-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
Affiliations:
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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><idno type="wicri:Area/Pmc/Checkpoint">000349</idno><idno type="wicri:Area/Ncbi/Merge">001D68</idno><idno type="wicri:Area/Ncbi/Curation">001D68</idno><idno type="wicri:Area/Ncbi/Checkpoint">001D68</idno><idno type="wicri:Area/Main/Merge">000443</idno><idno type="wicri:Area/Main/Curation">000443</idno><idno type="wicri:Area/Main/Exploration">000443</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. 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Elsharif</name></noRegion><name sortKey="Banerjee, Ashutosh" sort="Banerjee, Ashutosh" uniqKey="Banerjee A" first="Ashutosh" last="Banerjee">Ashutosh Banerjee</name><name sortKey="Buettner, Andrea" sort="Buettner, Andrea" uniqKey="Buettner A" first="Andrea" last="Buettner">Andrea Buettner</name><name sortKey="Buettner, Andrea" sort="Buettner, Andrea" uniqKey="Buettner A" first="Andrea" last="Buettner">Andrea Buettner</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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