Abstract
A homologous series (C6-C10) of 2-mercapto-4-alkanols was obtained by the addition of thioacetic acid to the respective alkenones and subsequent reduction with LiAlH4. Gas chromatographic separation of the stereoisomers was achieved using chiral stationary phases. Their absolute configurations were assigned by the correlation of 1H NMR data and enzyme-catalyzed kinetic resolutions. Odor thresholds and odor qualities were determined by capillary gas chromatography/olfactometry. Compared to the odor qualities reported for the isomeric 4-mercapto-2-alkanols, the homologous series of 2-mercapto-4-alkanols lacked fruity, tropical notes. There was no consistent correlation between the configurations and the odor qualities. However, the observed odor thresholds indicated the importance of the configuration of the asymmetric center bearing the hydroxyl group and the alkyl substituent. The length of this alkyl chain is a main driver for the odor properties, ranging from pungent, vegetable to earthy, mushroom notes.
Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
