3-sulfanylhexyl dodecanoate | 943221-52-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-sulfanylhexyl dodecanoate
• 英文别名: 3-Sulfanylhexyl Dodecanoate
• CAS: 943221-52-1
• 化学式: C₁₈H₃₆O₂S
• 分子量: 316.549
• InChiKey: WTIXFZHNOBZELM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  21
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  27.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  月桂酰氯 、 3-巯基-1-己醇 以 二氯甲烷 为溶剂， 反应 18.0h， 以93.7%的产率得到3-sulfanylhexyl dodecanoate
  参考文献：
  名称：

  Volatile Organic Sulfur-Containing Constituents in Poncirus trifoliata (L.) Raf. (Rutaceae)

  摘要：

  During our screening of plant materials to find new natural fragrance and flavor ingredients, we discovered two series of 3-sulfanylalkyl alkanoates in a peel extract of fruits of wild-growing Poncirus trifoliata (L.) Raf. (Rutaceae), a species closely related to Citrus. The two series belong to alkanoates of 3-methyl-3-sulfanylbutan-1-ol and 3-sulfanylhexan-1-ol, respectively, and thus are members of a family of natural molecules having in common a 1,3-positioned O,S moiety. The alkanoate residues comprise all even-numbered saturated fatty acids from C2 (acetate) to C18 (octadecanoate). Among the 20 sulfur-containing compounds identified, 14 are described for the first time as naturally occurring in a botanical species. Several cysteine-S-conjugates were synthesized as hypothetical precursors of the new volatile sulfur-containing constituents, where after S-(3-hydroxy-1,1-dimethylpropyl)-L-cysteine, S-[3-(acetyloxy)-1,1-dimethylpropyl]-L-cysteine, and S-[1-(2-hydroxyethyl)butyl]-L-cysteine were identified in the fruit peel. No cysteine-S-conjugates were detected in the fruit juice.

  DOI：

  10.1021/jf063453h

文献信息

• Volatile Organic Sulfur-Containing Constituents in <i>Poncirus trifoliata</i> (L.) Raf. (Rutaceae)
  作者：Christian Starkenmann、Yvan Niclass、Sina Escher

  DOI：10.1021/jf063453h

  日期：2007.5.1

  During our screening of plant materials to find new natural fragrance and flavor ingredients, we discovered two series of 3-sulfanylalkyl alkanoates in a peel extract of fruits of wild-growing Poncirus trifoliata (L.) Raf. (Rutaceae), a species closely related to Citrus. The two series belong to alkanoates of 3-methyl-3-sulfanylbutan-1-ol and 3-sulfanylhexan-1-ol, respectively, and thus are members of a family of natural molecules having in common a 1,3-positioned O,S moiety. The alkanoate residues comprise all even-numbered saturated fatty acids from C2 (acetate) to C18 (octadecanoate). Among the 20 sulfur-containing compounds identified, 14 are described for the first time as naturally occurring in a botanical species. Several cysteine-S-conjugates were synthesized as hypothetical precursors of the new volatile sulfur-containing constituents, where after S-(3-hydroxy-1,1-dimethylpropyl)-L-cysteine, S-[3-(acetyloxy)-1,1-dimethylpropyl]-L-cysteine, and S-[1-(2-hydroxyethyl)butyl]-L-cysteine were identified in the fruit peel. No cysteine-S-conjugates were detected in the fruit juice.