Determination of the Absolute Configurations and Sensory Properties of the Enantiomers of a Homologous Series (C6-C10) of 2-Mercapto-4-alkanones
Determination of the Absolute Configurations and Sensory Properties of the Enantiomers of a Homologous Series (C6-C10) of 2-Mercapto-4-alkanones
复制标题
2-巯基-4-烷酮同系系列 (C6-C10) 对映体的绝对构型和感官特性的测定
DOI：
10.1021/acs.jafc.8b06599
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发表时间：
2019
影响因子：
6.1
通讯作者：
Engel Karl-Heinz
中科院分区：
文献类型：
--
作者：
Kiske Christiane;Riegel Anja Devenie;Hopf Ronja;Kvindt Anna;Poplacean Iulia;Taniguchi Tohru;Swamy Mahadeva M. M.;Monde Kenji;Eisenreich Wolfgang;Engel Karl-Heinz
通过相应外消旋 2-乙酰硫基-4-烷酮的脂肪酶催化动力学拆分获得了 2-巯基-4-烷酮同系系列 (C6–C10) 的对映体。它们的构型通过振动圆二色性和基于 1 H NMR 各向异性的方法进行分配。气味阈值和气味质量通过使用手性固定相的毛细管气相色谱-嗅觉测定法测定。链长 C7 和 C8 的气味阈值具有最小值。除链长C8外，其他同系物的对映体表现出相似的气味阈值。气味质量范围从刺激性 (C5) 到蘑菇 (C9 和 C10)，与已知的相应 1-alken-3-one 少一个 C 原子的气味类似。与它们的位置异构体（4-巯基-2-烷酮）相比，所研究的2-巯基-4-烷酮不符合“热带嗅觉团”（即具有1,3-氧-硫官能团和取代基特定排列的化合物）的要求。
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 and1H 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).