| Title: | Analytical and Sensory Characterization of the Stereoisomers of 3-Mercaptocycloalkanones and 3-Mercaptocycloalkanols |
| Author(s): | Wakabayashi M; Wakabayashi H; Riegel AD; Eisenreich W; Engel KH; |
| Address: | "College of Bioresource Sciences, Nihon University, Kameino 1866, 252-0880 Fujisawa, Japan. Lehrstuhl fur Allgemeine Lebensmitteltechnologie, Technische Universitat Munchen, Maximus-von-Imhof-Forum 2, D-85354 Freising-Weihenstephan, Germany. Lehrstuhl fur Biochemie, Technische Universitat Munchen, Lichtenbergstrasse 4, D-85747 Garching, Germany" |
| ISSN/ISBN: | 1520-5118 (Electronic) 0021-8561 (Linking) |
| Abstract: | "3-Mercaptocycloalkanones and 3-mercaptocycloalkanols (chain lengths C5-C7) were obtained by addition of thioacetic acid to the respective 2-cycloalken-1-ones and subsequent enzyme-mediated hydrolysis and reduction with LiAlH(4), respectively. The stereoisomers were separated via capillary gas chromatography using chiral stationary phases. Their configurations were determined based on (1)H NMR data and enzyme-catalyzed kinetic resolutions. Odor thresholds and odor qualities were assessed by capillary gas chromatography/olfactometry. Compared to the analogous acyclic 4-mercapto-2-alkanones and 4-mercapto-2-alkanols, the cyclic polyfunctional thiols lacked fruity, tropical notes; the perceived odor properties ranged from cooked, roasted vegetables and meat types to onion-related notes. The odor thresholds of the enantiomers of the 3-mercaptocycloalkanones were mainly impacted by their ring size rather than their configuration. For the 3-mercaptocycloalkanols, the (S)-configuration at the stereogenic center bearing the thiol group and the relative configuration of the second asymmetric center with the hydroxyl group were of importance for low odor thresholds" |
| Keywords: | Adult Cycloparaffins/*chemistry/metabolism Female Gas Chromatography-Mass Spectrometry Humans Magnetic Resonance Spectroscopy Male Middle Aged Molecular Structure Odorants/analysis Olfactometry Smell Stereoisomerism Sulfhydryl Compounds/*chemistry/metabol; |
| Notes: | "MedlineWakabayashi, Motoko Wakabayashi, Hidehiko Riegel, Anja Devenie Eisenreich, Wolfgang Engel, Karl-Heinz eng 2020/06/17 J Agric Food Chem. 2020 Jul 8; 68(27):7184-7193. doi: 10.1021/acs.jafc.0c03113. Epub 2020 Jun 26" |
