(S,10Z,12E)-14-hydroxynonadeca-10,12-dienoic-13,14-d2 acid | 135106-71-7

• 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: (S,10Z,12E)-14-hydroxynonadeca-10,12-dienoic-13,14-d2 acid
• CAS: 135106-71-7
• 化学式: C₁₉H₃₄O₃
• 分子量: 312.461
• InChiKey: JHFOVTLNYHMZSE-PUBYJVNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.25
• 重原子数：
  22.0
• 可旋转键数：
  15.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  57.53
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (S,10Z,12E)-14-hydroxynonadeca-10,12-dienoic-13,14-d2 acid 以 水 为溶剂， 反应 48.0h， 生成 (R)-(+)-γ-nonalactone 、 (S)-二羟基-5-戊基-2(3H)-呋喃酮 、 (5S)-5-pentyldihydrofuran-2(3H)-one-4,5-d2 、 (5S)-5-pentyldihydrofuran-2(3H)-one-4-d
  参考文献：
  名称：

  Stereochemistry of the microbial generation of .delta.-decanolide, .gamma.-dodecanolide, and .gamma.-nonanolide from C18 13-hydroxy, C18 10-hydroxy, and C19 14-hydroxy unsaturated fatty acids

  摘要：

  (S)-delta-Decanolide (4) was isolated from cultures of Cladosporium suaveolens after the microorganism was fed either (S)- or (R,S)-coriolic acid (1). Feeding (R,S)-10-hydroxyoctadec-(8E)-enoic acid (2) to Yarrowia lipolytica produced (S)-gamma-dodecanolide. When (S)-homocoriolic acid (3) was fed to C.suaveolens, gamma-nonalide slightly enriched in the S enantiomer was produced. At some stage in the biodegradation of 3, an inversion of configuration, from S to R, occurred and was accompanied by the loss of the hydrogen atom originally present on C-14, as GLC/MS analysis of the products of feeding C. suaveolens with dideuterated 10 showed.

  DOI：

  10.1021/jo00018a001
• 作为产物：
  描述：

  triphenyl (non-3-yn-1-yl)phosphonium bromide 在 Lindlar's catalyst lithium hydroxide 、 potassium tert-butylate 、 氧气 、 sodium 2-mercaptoacetate 、 氘 作用下， 以 水 为溶剂， 生成 (S,10Z,12E)-14-hydroxynonadeca-10,12-dienoic-13,14-d2 acid
  参考文献：
  名称：

  Stereochemistry of the microbial generation of .delta.-decanolide, .gamma.-dodecanolide, and .gamma.-nonanolide from C18 13-hydroxy, C18 10-hydroxy, and C19 14-hydroxy unsaturated fatty acids

  摘要：

  (S)-delta-Decanolide (4) was isolated from cultures of Cladosporium suaveolens after the microorganism was fed either (S)- or (R,S)-coriolic acid (1). Feeding (R,S)-10-hydroxyoctadec-(8E)-enoic acid (2) to Yarrowia lipolytica produced (S)-gamma-dodecanolide. When (S)-homocoriolic acid (3) was fed to C.suaveolens, gamma-nonalide slightly enriched in the S enantiomer was produced. At some stage in the biodegradation of 3, an inversion of configuration, from S to R, occurred and was accompanied by the loss of the hydrogen atom originally present on C-14, as GLC/MS analysis of the products of feeding C. suaveolens with dideuterated 10 showed.

  DOI：

  10.1021/jo00018a001