(10E)-9-hydroxy-13-oxo-10-octadecenoic acid | 54232-62-1

• 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: (10E)-9-hydroxy-13-oxo-10-octadecenoic acid
• 英文别名: 9-Oxo-13-hydroxy-trans-10-octadecensaeure；9-Hydroxy-13-oxo-10-octadecenoic acid；(E)-9-hydroxy-13-oxooctadec-10-enoic acid
• CAS: 54232-62-1
• 化学式: C₁₈H₃₂O₄
• 分子量: 312.45
• InChiKey: HOWCTVFHRUJMDQ-GXDHUFHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  13(s)-羟基-9z,11e-十八二烯酸 在 ferrous ammonium sulphate 、 乙二胺四乙酸 、 双氧水 作用下， 以 phosphate buffer 、 氯仿 为溶剂， 反应 4.0h， 生成 (10E)-9-hydroxy-13-oxo-10-octadecenoic acid 、 (11E)-9,10-epoxy-13-hydroxy-11-octadecenoic acid 、 (9Z,11E)-13-氧代-9,11-十八碳二烯酸
  参考文献：
  名称：

  Free radical oxidation of coriolic acid (13-(S)-hydroxy-9Z,11E-octadecadienoic Acid)

  摘要：

  The reaction of (13S,9Z, 11E)-13-hydroxy-9,11-octadecadienoic acid (1a), one of the major peroxidation products of linoleic acid and an important physiological mediator, with the Fenton reagent (Fe2+/EDTA/H2O2) was investigated. In phosphate buffer, pH 7.4, the reaction proceeded with > 80% substrate consumption after 4h to give a defined pattern of products, the major of which were isolated as methyl esters and were subjected to complete spectral characterization. The less polar product was identified as (9Z, 11E)-13-oxo-9,11-octadecadienoate (2) methyl ester (40% yield). Based on 2D NMR analysis the other two major products were formulated as (11E)-9,10-epoxy-13-hydroxy-11-octadecenoate(3) methyl ester (15% yield) and (10E)-9-hydroxy- 13-oxo-10-octadecenoate (4) methyl ester (10% yield). Mechanistic experiments, including deuterium labeling, were consistent with a free radical oxidation pathway involving as the primary event H-atom abstraction at C-13, as inferred from loss of the original S configuration in the reaction products. Overall, these results provide the first insight into the products formed by oxidation of la with the Fenton reagent, and hint at novel formation pathways of the hydroxyepoxide 3 and hydroxyketone 4 of potential (patho)physiological relevance in settings of oxidative stress. (c) 2005 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2005.01.005

文献信息

• ANTI-INFLAMMATORY AGENT CONTAINING RARE FATTY ACID
  申请人：Kyoto University

  公开号：EP3097910A1

  公开（公告）日：2016-11-30

  The present invention provides an anti-inflammatory agent containing a rare fatty acid such as hydroxylated fatty acid, oxo fatty acid and the like, and further, food, pharmaceutical product and the like containing the anti-inflammatory agent.

  本发明提供了一种含有稀有脂肪酸（如羟化脂肪酸、氧代脂肪酸等）的消炎剂，以及含有该消炎剂的食品、药品等。
• Free radical oxidation of coriolic acid (13-(S)-hydroxy-9Z,11E-octadecadienoic Acid)
  作者：P. Manini、E. Camera、M. Picardo、A. Napolitano、M. d’Ischia

  DOI：10.1016/j.chemphyslip.2005.01.005

  日期：2005.4

  The reaction of (13S,9Z, 11E)-13-hydroxy-9,11-octadecadienoic acid (1a), one of the major peroxidation products of linoleic acid and an important physiological mediator, with the Fenton reagent (Fe2+/EDTA/H2O2) was investigated. In phosphate buffer, pH 7.4, the reaction proceeded with > 80% substrate consumption after 4h to give a defined pattern of products, the major of which were isolated as methyl esters and were subjected to complete spectral characterization. The less polar product was identified as (9Z, 11E)-13-oxo-9,11-octadecadienoate (2) methyl ester (40% yield). Based on 2D NMR analysis the other two major products were formulated as (11E)-9,10-epoxy-13-hydroxy-11-octadecenoate(3) methyl ester (15% yield) and (10E)-9-hydroxy- 13-oxo-10-octadecenoate (4) methyl ester (10% yield). Mechanistic experiments, including deuterium labeling, were consistent with a free radical oxidation pathway involving as the primary event H-atom abstraction at C-13, as inferred from loss of the original S configuration in the reaction products. Overall, these results provide the first insight into the products formed by oxidation of la with the Fenton reagent, and hint at novel formation pathways of the hydroxyepoxide 3 and hydroxyketone 4 of potential (patho)physiological relevance in settings of oxidative stress. (c) 2005 Elsevier Ireland Ltd. All rights reserved.