S-[1-甲基-1-(4-甲基-2-氧代环己基)乙基]硫代乙酸酯 | 94293-57-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: S-[1-甲基-1-(4-甲基-2-氧代环己基)乙基]硫代乙酸酯
• 英文名称: 8-acetylthio-para-menthan-3-one
• 英文别名: p-Mentha-8-Thiol-3-One Acetate；S-[2-(4-methyl-2-oxocyclohexyl)propan-2-yl] ethanethioate
• CAS: 94293-57-9
• 化学式: C₁₂H₂₀O₂S
• mdl: MFCD02683081
• 分子量: 228.356
• InChiKey: AMXPURQVAMENCC-UHFFFAOYSA-N

物化性质

• 沸点：
  320.5±15.0 °C(Predicted)
• 密度：
  1.053±0.06 g/cm3(Predicted)
• LogP：
  2.49
• 保留指数：
  1603.5

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.833
• 拓扑面积：
  59.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  S-[1-甲基-1-(4-甲基-2-氧代环己基)乙基]硫代乙酸酯 在 Passiflora edulis wall-bound hydrolase 作用下， 生成 8-巯基马来酮
  参考文献：
  名称：

  Determination and Isolation of a Thioesterase from Passion Fruit (Passiflora edulis Sims) That Hydrolyzes Volatile Thioesters

  摘要：

  Volatile organosulfur compounds (VOSCs) are high impact aroma chemicals characteristic of tropical fruits which are active as both free thiols and the respective thioesters. Using a simple and sensitive colorimetric enzyme assay, a thioesterase activity toward VOSCs has been identified in ripening purple passion fruit (Passiflora edulis Sims). The assay was based on determining the release of free thiols from 2-methyl-3-furanthiol acetate using Ellman's reagent. The major thioesterase in the fruit was found to be a wall-bound protein in the mesocarp. The extracted enzyme activity was purified 150-fold and shown to be associated with a 43 kDa monomeric serine hydrolase which was selectively labeled with a fluorophosphonate suicide probe. MS-MS sequencing identified the thioesterase as a class 13 glycoside hydrolase, most similar to pectin acetylesterase, an enzyme involved in cell wall modifications in the peel of a number of fruit. Our results suggest that cell wall hydrolases in tropical fruit may have additional useful roles in biotransforming VOSCs.

  DOI：

  10.1021/jf800793q

文献信息

• Flavouring and odorant thiols from renewable natural resources by InIII-catalysed hydrothioacetylation and lipase-catalysed solvolysis
  作者：Reine-Marie Dia、Rim Belaqziz、Abderrahmane Romane、Sylvain Antoniotti、Elisabet Duñach

  DOI：10.1016/j.tetlet.2010.02.081

  日期：2010.4

  A chemoenzymatic access to thiol compounds, including ethyl 3-thiobutanoate, 3-thio-p-menthene and 8-thio-p-menthan-2-one, three compounds of interest in flavour and fragrance chemistry presenting various fruity notes, is proposed. It involves an indium(III)-catalysed hydrothioacetylation of renewable precursors followed by an enzymatic solvolysis of the obtained thioesters by lipases in aqueous or organic solvents. (c) 2010 Elsevier Ltd. All rights reserved.