1-stearoyl-2-(13-oxo-9,11-tridecadienoyl)-sn-3-glycerophosphocholine | 477202-46-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油磷脂
• 英文名称: 1-stearoyl-2-(13-oxo-9,11-tridecadienoyl)-sn-3-glycerophosphocholine
• CAS: 477202-46-3
• 化学式: C₃₉H₇₂NO₉P
• 分子量: 729.976
• InChiKey: LVEJVYVVHFPSFO-UVFMICAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.95
• 重原子数：
  50.0
• 可旋转键数：
  36.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  128.26
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  甲醇 、 1-stearoyl-2-(13-oxo-9,11-tridecadienoyl)-sn-3-glycerophosphocholine 在 iron(II) sulfate 作用下， 生成
  参考文献：
  名称：

  The rapid oxidative degradation of a phosphatidylcholine bearing an oxidatively modified acyl chain with a 2,4-dienal terminal

  摘要：

  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.

  DOI：

  10.1016/j.chemphyslip.2004.04.004
• 作为产物：
  描述：

  (9Z,11E,15Z)-13-hydroperoxy-9,11,15-octadecatrienoic acid methyl ester 在 4-二甲氨基吡啶 、 iron(II) sulfate 、 N,N'-二环己基碳二亚胺 作用下， 反应 7.0h， 生成 1-stearoyl-2-(13-oxo-9,11-tridecadienoyl)-sn-3-glycerophosphocholine
  参考文献：
  名称：

  The rapid oxidative degradation of a phosphatidylcholine bearing an oxidatively modified acyl chain with a 2,4-dienal terminal

  摘要：

  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.

  DOI：

  10.1016/j.chemphyslip.2004.04.004

文献信息

• First synthesis of phosphatidylcholine and cholesteryl derivatives bearing an unsaturated aldehyde residue
  作者：Arnold N. Onyango、Teruhiko Nitoda、Takao Kaneko、Mitsuyoshi Matsuo、Shuhei Nakajima、Naomichi Baba

  DOI：10.1039/b206231n

  日期：——

  The first synthesis of phosphatidylcholine and cholesteryl esters bearing a shortened acyl chain with a 2,4-dienal terminal is described.

  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。