Influence of the Stereochemistry on the Sensory Properties of 4-Mercapto-2-heptanol and Its Acetyl-Derivatives
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- 作者：Svenja N枚renberg ; Bastian Reichardt ; Verena Andelfinger ; Wolfgang Eisenreich ; Karl-Heinz Engel
- 刊名：Journal of Agricultural and Food Chemistry
- 出版年：2013
- 出版时间：March 6, 2013
- 年：2013
- 卷：61
- 期：9
- 页码：2062-2069
- 全文大小：293K
- 年卷期：v.61,no.9(March 6, 2013)
- ISSN：1520-5118
文摘
4-Mercapto-2-heptanol, previously described in cooked bell pepper, was used to determine the impact of the stereochemistry on the sensory properties of a thiol with a 1,3-oxygen鈥搒ulfur functionality. In addition, the acetyl-derivatives 4-acetylthio-2-heptanol, 4-mercapto-2-heptyl acetate and 4-acetylthio-2-heptyl acetate were investigated. The synthesized stereoisomers were separated via capillary gas chromatography (GC) using chiral stationary phases. The GC orders of elution were determined by assigning the absolute configurations via NMR analysis in combination with lipase-catalyzed kinetic resolutions. Odor thresholds and odor properties were determined by means of GC/Olfactometry. The data revealed that the sensory properties of the investigated compounds are not only significantly influenced by the acetylation but also by the configurations of the two asymmetric centers.