(8E,10S)-10-hydroxy-8-octadecenoic acid

• 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: (8E,10S)-10-hydroxy-8-octadecenoic acid
• 英文别名: 10(S)-hydroxy-8(E)-octadecenoic acid；10(S)-hydroxy-8(E)-octadecenoic；(E,10S)-10-hydroxyoctadec-8-enoic acid
• 化学式: C₁₈H₃₄O₃
• 分子量: 298.466
• InChiKey: RXBFKZNLXJKTLQ-VMEIHUARSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  21
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  油酸 在 Pseudomonas aeruginosa NRRL B-18602 作用下， 以 水 为溶剂， 反应 48.0h， 生成 (8E,10S)-10-hydroxy-8-octadecenoic acid
  参考文献：
  名称：

  10（S）-羟基-8（E）-十八烯酸，油酸转化为7,10-二羟基-8（E）-十八烯酸的中间体

  摘要：

  AbstractThe new microbial isolate Pseudomonas aeruginosa (PR3) has been reported to produce from oleic acid a new compound, 7,10‐dihydroxy‐8(E)‐octadecenoic acid (DOD), with 10‐hydroxy‐8‐octadecenoic acid (HOD) being a probable intermediate. The production of DOD involves the introduction of two hydroxyl groups at carbon numbers 7 and 10, and a rearrangement of the double bond from carbons 9–10 to 8–9. It has been shown that the 8–9 unsaturation of HOD was possibly in the cis configuration. Now we report that the rearranged double bond of HOD is trans rather than cis, as determined by spectral data. Also, it was found that the 10‐hydroxyl was in the S‐configuration as determined by gas chromatographic separation of R‐ and S‐isomers after preparation of the (−)‐menthoxycarbonyl derivative of the hydroxyl group followed by oxidative cleavage of the double bond and methyl esterification. This latter result coincides with our recent finding that the main final product, DOD, is in the 7(S),10(S)‐dihydroxy configuration. In addition, a minor isomer of HOD (about 3%) with the 10(R)‐hydroxyl configuration was also detected. From the data obtained herein, we concluded that 10(S)‐hydroxy‐8(E)‐octadecenoic acid is the probable intermediate in the bioconversion of oleic acid to 7(S),10(S)‐dihydroxy‐8(E)‐octadecenoic acid by PR3.

  DOI：

  10.1007/s11746-000-0015-7

文献信息

• Production of 10(S)-hydroxy-8(E)-octadecenoic acid mono-estolides by lipases in non-aqueous media
  作者：I. Martin-Arjol、M. Busquets、A. Manresa

  DOI：10.1016/j.procbio.2012.12.006

  日期：2013.2

  In this study, Novozym 435, a lipase B from Candida antarctica, was used for fatty acid polymerization. For the first time, an apolar reaction media, n-hexane, was used to synthesize in vitro estolides from trans-hydroxy-fatty acids derived from the biotransformation of oleic acid by Pseudomonas aeruginosa 42A2 NCIMB 40045. We studied the effects of the substrate, the enzyme ratio, the enzyme stability

  在这项研究中，Novozym 435，一种来自南极念珠菌的脂肪酶 B，用于脂肪酸聚合。首次使用非极性反应介质正己烷从铜绿假单胞菌 42A2 NCIMB 40045 生物转化油酸后衍生的反式羟基脂肪酸合成体外 estolides。我们研究了底物的影响，酶比例、酶稳定性和生物催化剂的可重复使用性。为了确定形成的低聚物的结构，使用液相色谱质谱法和 MALDI-TOF 质谱法，其中 DHB 基质用氢氧化锂中和，以获得更简单的质谱。以30%的反应收率合成了由(10S)-HOME的两个单元组成的Estolides。最后筛选出各种脂肪酶，另一种非极性有机溶剂异辛烷，