methyl ricinoleate | 93451-99-1

• 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: methyl ricinoleate
• 英文别名: Methyl-12-hydroxy-cis-9-octadecenoat；Methyl 13-hydroxy-cis-9-octadecenoate；methyl (Z)-13-hydroxyoctadec-9-enoate
• CAS: 93451-99-1
• 化学式: C₁₉H₃₆O₃
• 分子量: 312.493
• InChiKey: QVPBDPLANOEFJC-NTMALXAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  22
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl ricinoleate 在 N-甲基咪唑 、 lithium hydroxide 、 2,6-二氯苯甲酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 [2-[(Z)-13-[tert-butyl(dimethyl)silyl]oxyoctadec-9-enoyl]oxy-3-hexadecanoyloxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
  参考文献：
  名称：

  A Rapid Condensation between Lysophosphorylcholine and Fatty Acids with an Easily Separable Amine Base

  摘要：

  以2，6-Cl2C6H3COCl和1-甲基咪唑为原料，标题缩合反应在室温下12小时内完成，时间短于标准DCC/DMAP体系。通过色谱法容易地从粗产物中分离出1-甲基咪唑，是本试剂体系的额外优势。

  DOI：

  10.1055/s-2005-871973
• 作为产物：
  描述：

  13-hydroxy-cis-9-octadecenoic acid 、 三甲基硅烷化重氮甲烷 以 正己烷 为溶剂， 反应 0.5h， 生成 methyl ricinoleate
  参考文献：
  名称：

  Characterization of hydroxy fatty acid dehydrogenase involved in polyunsaturated fatty acid saturation metabolism in Lactobacillus plantarum AKU 1009a

  摘要：

  Hydroxy fatty acid dehydrogenase, which is involved in polyunsaturated fatty acid saturation metabolism in Lactobacillus plantarum AKU 1009a, was cloned, expressed, purified, and characterized. The enzyme preferentially catalyzed NADH-dependent hydrogenation of oxo fatty acids over NAD(+)-dependent dehydrogenation of hydroxy fatty acids. In the dehydrogenation reaction, fatty acids with an internal hydroxy group such as 10-hydroxy-cis-12-octadecenoic acid, 12-hydroxy-cis-9-octadecenoic acid, and 13-hydroxy-cis-9-octadecenoic acid served as better substrates than those with alpha- or beta-hydroxy groups such as 3-hydroxyoctadecanoic acid or 2-hydroxyeicosanoic acid. The apparent Km value for 10-hydroxy-cis-12-octadecenoic acid (HYA) was estimated to be 38 mu M with a k(cat) of 7.6 x 10(-3) s(-1). The apparent K-m value for 10-oxo-cis-12-octadecenoic acid (KetoA) was estimated to be 1.8 mu M with a k(cat) of 5.7 x 10(-1) s(-1). In the hydrogenation reaction of KetoA, both (R)- and (S)-HYA were generated, indicating that the enzyme has low stereoselectivity. This is the first report of a dehydrogenase with a preference for fatty acids with an internal hydroxy group. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2015.03.020