(9Z,11E,15Z)-13-hydroperoxy-9,11,15-octadecatrienoic acid methyl ester | 74879-02-0

• 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: (9Z,11E,15Z)-13-hydroperoxy-9,11,15-octadecatrienoic acid methyl ester
• 英文别名: methyl 13-hydroperoxy-cis-9,trans-11,cis-15-octadecatrienoate；methyl 13-hydroperoxy-9,11,15-octadecatrienoate；methyl (9Z,11E,15Z)-13-hydroperoxyoctadeca-9,11,15-trienoate
• CAS: 74879-02-0
• 化学式: C₁₉H₃₂O₄
• 分子量: 324.461
• InChiKey: BYBABUPPOWFKIP-CTIIKXKSSA-N

物化性质

• 沸点：
  447.3±45.0 °C(Predicted)
• 密度：
  0.980±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.22
• 重原子数：
  23.0
• 可旋转键数：
  14.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (9Z,11E,15Z)-13-hydroperoxy-9,11,15-octadecatrienoic acid methyl ester 在 二-叔-丁基过氧草酸酯 作用下， 以 苯 为溶剂， 反应 5.0h， 生成 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  脂质的氧化。九。亚油酸甲酯和亚麻酸甲酯氢过氧化物在溶液中的分解

  摘要：

  在苯中于 50 °C 和真空下研究了由二叔丁基二过氧草酸和钴离子诱导的亚油酸氢过氧化物 (LOOH) 分解，以阐明降解机制。主要产品为二聚体（LOOL）、氧代二烯、羟基二烯和环氧羟基烯（和/或环氧氧烯）。推测这些产物分别由L·和LOO·自由基的重组、LO·自由基的β-断裂、LO·自由基的夺氢和LOO·自由基的分子内环氧化作用形成。还研究了亚麻酸甲酯氢过氧化物 (L'OOH) 的分解。主要产物为二聚体、氧代三烯、羟基三烯和硫代巴比妥酸反应物，推测是由L'OO·自由基分子内环化形成的。

  DOI：

  10.1246/bcsj.57.3177
• 作为产物：
  描述：

  Γ-十八碳三烯酸 在 soybean lipoxygenase 、 氧气 作用下， 以 various solvent(s) 为溶剂， 反应 6.0h， 生成 (9Z,11E,15Z)-13-hydroperoxy-9,11,15-octadecatrienoic acid methyl ester
  参考文献：
  名称：

  First synthesis of phosphatidylcholine and cholesteryl derivatives bearing an unsaturated aldehyde residue

  摘要：

  首次合成了具有2,4-二烯醛末端的短链酰基的磷脂酰胆碱和胆固醇酯。

  DOI：

  10.1039/b206231n

文献信息

• Stereochemical course of the autooxidative cyclization of lipid hydroperoxides to prostaglandin-like bicyclic endoperoxides
  作者：D. E. O'Connor、E. D. Mihelich、M. C. Coleman

  DOI：10.1021/ja00324a028

  日期：1984.6

  Stereochimie de la cyclisation autooxydante de 2 hydroperoxydes d'acides gras polyinsatures, les hydroperoxy-13 undecatriene-9,11,15 oate de methyle et hydroperoxy-9 undecatriene-6,10,12 oate de methyle

  Stereochimie de la cyclisation autooxydante de 2 hydroperoxydes d'acides gras polyinsatures, les hydroperoxy-13 undecatriene-9,11,15 oate demethyle ethydroperoxy-9 undecatriene-6,10,12 oate demethyle
• A hydroperoxy-epidioxide from the autoxidation of a hydroperoxide of methyl linolenate
  作者：Henry W.-S. Chan、Jennifer A. Matthew、David T. Coxon

  DOI：10.1039/c39800000235

  日期：——

  Unlike autoxidation of linolenic acid or methyl linolenate which yields mixtures of hydroperoxy-epidioxides, sequential oxidation employing an enzymic first step followed by an autoxidation step can give rise to a single hydroperoxy-epidioxide.

  与亚麻酸或亚油酸甲酯的自氧化产生氢过氧-环氧乙烷的混合物不同，采用酶促第一步继之以自氧化步骤的顺序氧化可产生单个氢过氧-环氧丙烷。
• The rapid oxidative degradation of a phosphatidylcholine bearing an oxidatively modified acyl chain with a 2,4-dienal terminal
  作者：Arnold N Onyango、Shuhei Nakajima、Takao Kaneko、Mitsuyoshi Matsuo、Naomichi Baba

  DOI：10.1016/j.chemphyslip.2004.04.004

  日期：2004.8

  Phosphatidyleholines (PCs) having an acyl chain with a 2,4-dienal terminal are expected to be important bioactive compounds formed during lipid peroxidation in vivo. However, they have not been isolated from biological tissues. Here we used electrospray mass spectroscopy to investigate whether a high autoxidative instability may contribute to the difficulty in detecting one such compound, 13-oxo-9,11-tridecadienoyl PC (OTDA-PC, 1). Although we found that pure, synthetic OTDA-PC was very stable, OTDA-PC formed during the decomposition of a PC bearing the 13-hydroperoxide of alpha-linolenic acid (PC-LNA-OOH, 2) was readily converted (i) anaerobically to its corresponding acid PC, 13-carboxy-9,11-tridecadienoyl PC, 3; (ii) aerobically to other bioactive aldehyde (or acid) PC species that have been detected in atherosclerotic tissues. We attribute the high oxidative instability of OTDA-PC to a high vulnerability of its carbonyl hydrogen [H-C(=O)R] to abstraction by lipid-derived radicals, and propose mechanisms for its conversion to the other oxidised PC species (vide supra). (C) 2004 Elsevier Ireland Ltd. All rights reserved.
• Isolation and characterization of bicycloendoperoxides derived from methyl linolenate
  作者：David E. O'Connor、Edward D. Mihelich、Milton C. Coleman

  DOI：10.1021/ja00391a056

  日期：1981.1