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J Agric Food Chem

Title:		Determination of the Absolute Configurations and Sensory Properties of the Enantiomers of a Homologous Series (C6-C10) of 2-Mercapto-4-alkanones
Author(s):		Kiske C; Riegel AD; Hopf R; Kvindt A; Poplacean I; Taniguchi T; Swamy MMM; Monde K; Eisenreich W; Engel KH;
Address:		"Lehrstuhl fur Allgemeine Lebensmitteltechnologie , Technische Universitat Munchen , Maximus-von-Imhof-Forum 2 , D-85354 Freising-Weihenstephan , Germany. Frontier Research Center for Advanced Material and Life Science, Faculty of Advanced Life Science , Hokkaido University , Kita 21 Nishi 11 , 001-0021 Sapporo , Japan. Lehrstuhl fur Biochemie , Technische Universitat Munchen , Lichtenbergstrasse 4 , D-85747 Garching , Germany"
Journal Title:		J Agric Food Chem
Year:		2019
Volume:		20190114
Issue:		4
Page Number:		1187 - 1196
DOI:		10.1021/acs.jafc.8b06599
ISSN/ISBN:		1520-5118 (Electronic) 0021-8561 (Linking)
Abstract:		"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 (1)H 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)"
Keywords:		"Adult Chromatography, Gas Female Humans Molecular Structure Odorants/*analysis Olfactometry Smell Stereoisomerism Sulfhydryl Compounds/*chemistry Volatile Organic Compounds/*chemistry Young Adult 1H NMR spectroscopy 2-mercapto-4-alkanones Vcd absolute con;"
Notes:		"MedlineKiske, Christiane Riegel, Anja Devenie Hopf, Ronja Kvindt, Anna Poplacean, Iulia Taniguchi, Tohru Swamy, Mahadeva M M Monde, Kenji Eisenreich, Wolfgang Engel, Karl-Heinz eng 2019/01/04 J Agric Food Chem. 2019 Jan 30; 67(4):1187-1196. doi: 10.1021/acs.jafc.8b06599. Epub 2019 Jan 14"