3-acetylthio-3-methylbutanal | 50746-14-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-acetylthio-3-methylbutanal
• 英文别名: β-acetylsulfanyl-isovaleraldehyde；β-Acetylmercapto-isovaleraldehyd；S-(2-methyl-4-oxobutan-2-yl) ethanethioate
• CAS: 50746-14-0
• 化学式: C₇H₁₂O₂S
• 分子量: 160.237
• InChiKey: FFSINPZVFMCTHL-UHFFFAOYSA-N

物化性质

• 沸点：
  110 °C(Press: 20 Torr)
• 密度：
  1.050±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  59.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-acetylthio-3-methylbutanal 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 0.25h， 生成 3-巯基-3-甲基丁醛
  参考文献：
  名称：

  Aroma Extraction Dilution Analysis of Sauternes Wines. Key Role of Polyfunctional Thiols

  摘要：

  The aim of the present work was to investigate Sauternes wine aromas. In all wine extracts, polyfunctional thiols were revealed to have a huge impact. A very strong bacon-petroleum odor emerged at RI) 845 from a CP-Sil5-CB column. Two thiols proved to participate in this perception: 3-methyl-3-sulfanylbutanal and 2-methylfuran-3-thiol. A strong synergetic effect was evidenced between the two compounds. The former, never mentioned before in wines, and not found in the musts of this study, is most probably synthesized during fermentation. 3-Methylbut-2-ene-1-thiol, 3-sulfanylpropyl acetate, 3-sulfanylhexan-1-ol, and 3-sulfanylheptanal also contribute to the global aromas of Sauternes wines. Among other key odorants, the presence of a varietal aroma (R-terpineol), sotolon, fermentation alcohols (3-methylbutan-1-ol and 2-phenylethanol) and esters ( ethyl butyrate, ethyl hexanoate, and ethyl isovalerate), carbonyls (trans-non-2-enal and beta-damascenone), and wood flavors (guaiacol, vanillin, eugenol, beta-methyl-gamma-octalactone, and Furaneol) is worth stressing.

  DOI：

  10.1021/jf060814k
• 作为产物：
  描述：

  3-甲基-2-丁烯醛 、 硫代乙酸 在 哌啶 作用下， 反应 24.0h， 生成 3-acetylthio-3-methylbutanal
  参考文献：
  名称：

  巯基链烷醇同源序列中的结构-气味相关性。

  摘要：

  为了研究分子结构对巯基链烷醇的感官特性的影响，同源系列的1-巯基烷-3-醇，3-巯基烷-1-醇，2-巯基烷-1-醇，4-巯基烷-2-醇，3合成了-巯基-3-甲基烷烃-1-醇，1-巯基-2-甲基烷烃-3-醇，3-巯基-2-甲基烷烃-1-醇和2-乙基-3-巯基烷烃-1-醇。确定空气和气味质量的气味阈值，并将获得的结果与化学结构相关。感官特性受空间效应的强烈影响：所有同源序列均显示，在五个至七个碳原子之间的气味阈值最小，并且碳链长度的增加导致气味阈值呈指数增加。硫醇的嗅觉能力通过在硫醇基团的α位上的甲基或乙基取代以及在含巯基的碳原子上的另外的甲基或乙基而大大改善了。通过比较分子相似指数分析，可以建立3D-定量构效关系模型，该模型能够预测巯基链烷醇的气味阈值，与实验结果吻合良好。提供了49种巯基链烷醇的保留指数，NMR数据和质谱图，其中大多数是首次合成制备。能够预测巯基链烷醇的气味阈值，与实验结果

  DOI：

  10.1021/acs.jafc.7b01266

文献信息

• Mercapto alcohols and mercaptoalkyl esters
  申请人：Polak's Frutal Works B.V.

  公开号：US03970689A1

  公开（公告）日：1976-07-20

  New compounds having the formula ##EQU1## wherein R.sub.1 represents a hydrocarbon moiety having from 1 to 7 carbon toms, R.sub.2 is hydrogen, methyl or ethyl, and R.sub.3 is hydrogen, formyl or acetyl. The compounds are useful in the preparation, modification and intensification of a great variety of flavor and perfume compositions.

  新化合物的化学式为##EQU1## 其中R.sub.1代表具有1至7个碳原子的碳氢基团，R.sub.2是氢、甲基或乙基，R.sub.3是氢、甲酰基或乙酰基。这些化合物在制备、改性和增强各种口味和香水组合中非常有用。
• Catch et al., Journal of the Chemical Society, 1947, p. 1611
  作者：Catch et al.

  DOI：——

  日期：——
• COMPOUNDS AND METHODS FOR TRANS-MEMBRANE DELIVERY OF MOLECULES
  申请人：Aposense LTD.

  公开号：US20190008976A1

  公开（公告）日：2019-01-10

  A conjugate for delivery of drugs, such as genetic drugs, [e.g., siRNA, dsiRNA, or antisense oligonucleotides (ASO)]across biological membranes is provided. The conjugates of the Invention are capable of delivering drugs in both presence and absence of plasma proteins.
• US4053656A
  申请人：——

  公开号：US4053656A

  公开（公告）日：1977-10-11
• Aroma Extraction Dilution Analysis of Sauternes Wines. Key Role of Polyfunctional Thiols
  作者：Sabine Bailly、Vesna Jerkovic、Jacqueline Marchand-Brynaert、Sonia Collin

  DOI：10.1021/jf060814k

  日期：2006.9.1

  The aim of the present work was to investigate Sauternes wine aromas. In all wine extracts, polyfunctional thiols were revealed to have a huge impact. A very strong bacon-petroleum odor emerged at RI) 845 from a CP-Sil5-CB column. Two thiols proved to participate in this perception: 3-methyl-3-sulfanylbutanal and 2-methylfuran-3-thiol. A strong synergetic effect was evidenced between the two compounds. The former, never mentioned before in wines, and not found in the musts of this study, is most probably synthesized during fermentation. 3-Methylbut-2-ene-1-thiol, 3-sulfanylpropyl acetate, 3-sulfanylhexan-1-ol, and 3-sulfanylheptanal also contribute to the global aromas of Sauternes wines. Among other key odorants, the presence of a varietal aroma (R-terpineol), sotolon, fermentation alcohols (3-methylbutan-1-ol and 2-phenylethanol) and esters ( ethyl butyrate, ethyl hexanoate, and ethyl isovalerate), carbonyls (trans-non-2-enal and beta-damascenone), and wood flavors (guaiacol, vanillin, eugenol, beta-methyl-gamma-octalactone, and Furaneol) is worth stressing.