Determination of the Absolute Configurations and Sensory Properties of the Enantiomers of a Homologous Series (C6–C10) of 2‑Mercapto-4-alkanones

The enantiomers of a homologous series (C6–C10) of 2-mercapto-4-alkanones were obtained by lipase-catalyzed kinetic resolution of the corresponding racemic 2-acetylthio-4-alkanones. Their configurations were assigned via vibrational circular dichroism and 1H NMR anisotropy based methods. Odor thresh...

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Bibliographic Details
Published in:Journal of agricultural and food chemistry 2019-01, Vol.67 (4), p.1187-1196
Main Authors: Kiske, Christiane, Riegel, Anja Devenie, Hopf, Ronja, Kvindt, Anna, Poplacean, Iulia, Taniguchi, Tohru, Swamy, Mahadeva M. M, Monde, Kenji, Eisenreich, Wolfgang, Engel, Karl-Heinz
Format: Article
Language:English
Subjects:
Adult
Chromatography, Gas
Female
Humans
Molecular Structure
Odorants - analysis
Olfactometry
Smell
Stereoisomerism
Sulfhydryl Compounds - chemistry
Volatile Organic Compounds - chemistry
Young Adult
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Summary:The enantiomers of a homologous series (C6–C10) of 2-mercapto-4-alkanones were obtained by lipase-catalyzed kinetic resolution of the corresponding racemic 2-acetylthio-4-alkanones. Their configurations were assigned via vibrational circular dichroism and 1H NMR anisotropy based methods. Odor thresholds and odor qualities were determined by capillary gas chromatography–olfactometry using chiral stationary phases. There were minima of the odor thresholds for the chain lengths C7 and C8. Except for chain length C8, the enantiomers of the other homologues showed similar odor thresholds. The odor qualities ranged from pungent (C5) to mushroom (C9 and C10) and were similar to those known for the corresponding 1-alken-3-ones with one less C atom. In contrast to their positional isomers (4-mercapto-2-alkanones), the investigated 2-mercapto-4-alkanones do not meet the requirements of a “tropical olfactophore” (i.e., compounds possessing a 1,3-oxygen-sulfur functionality and specific arrangements of the substituents).
ISSN:0021-8561
1520-5118
DOI:10.1021/acs.jafc.8b06599