Lehrstuhl für Allgemeine Lebensmitteltechnologie, Technische Universität München , Maximus-von-Imhof-Forum 2, D-85350 Freising-Weihenstephan, Germany.
J Agric Food Chem. 2013 Mar 6;61(9):2062-9. doi: 10.1021/jf305447e. Epub 2013 Feb 25.
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-sulfur 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.
4-巯基-2-庚醇，先前在煮过的甜椒中被描述过，被用来确定立体化学对具有 1,3-氧-硫官能团的硫醇的感官特性的影响。此外，还研究了乙酰衍生物 4-乙酰硫代-2-庚醇、4-巯基-2-庚基乙酸酯和 4-乙酰硫代-2-庚基乙酸酯。通过使用手性固定相，通过毛细管气相色谱（GC）分离合成的立体异构体。通过 NMR 分析与脂肪酶催化动力学拆分相结合，确定绝对构型，从而确定 GC 洗脱顺序。通过 GC/嗅觉测定法测定气味阈值和气味特性。数据表明，所研究化合物的感官特性不仅受到乙酰化的显著影响，而且还受到两个不对称中心的构型的影响。
