10,12-Octadecadienoic acid, 9-hydroperoxy-, methyl ester, (E,E)- | 13974-49-7

• 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: 10,12-Octadecadienoic acid, 9-hydroperoxy-, methyl ester, (E,E)-
• 英文别名: methyl 9-hydroperoxyoctadeca-10,12-dienoate；methyl 9-hydroperoxy-cis-10,trans-12-octadecadienoate；methyl 9-(R,S)-hydroperoxy-10-trans,12-trans-octadecadienoate；methyl (12Z)-9-hydroperoxyoctadeca-10,12-dienoate
• CAS: 13974-49-7；32671-92-4；35152-24-0；60900-57-4；62560-98-9；65700-63-2；90760-89-7；90760-90-0；116181-15-8；116181-18-1；116181-20-5
• 化学式: C₁₉H₃₄O₄
• 分子量: 326.477
• InChiKey: NAIVAZYIMZYEHW-AJIFNOQSSA-N

物化性质

• 沸点：
  444.7±38.0 °C(Predicted)
• 密度：
  0.968±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.44
• 重原子数：
  23.0
• 可旋转键数：
  15.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.74
• 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：

  10,12-Octadecadienoic acid, 9-hydroperoxy-, methyl ester, (E,E)- 在 2-甲氧基丙烯 、 水 作用下， 生成 9(S)-HPODE
  参考文献：
  名称：

  Liquid chromatography–tandem mass spectrometry determination of human plasma 1-palmitoyl-2-hydroperoxyoctadecadienoyl-phosphatidylcholine isomers via promotion of sodium adduct formation

  摘要：

  Accumulation of phosphatidylcholine hydroperoxide (PCOOH), a primary oxidation product of phosphatidylcholine, in blood plasma has been observed in various pathological conditions, including atherosclerosis. In this study, we investigated the use of liquid chromatography-tandem mass spectrometry (LC-MS/MS) to develop a method for accurate quantification of PCOOH (1-palmitoyl-2-hydroperoxy-octadecadienoyl-sn-glycero-3-phosphocholine, 16:0/HpODE PC), focusing on isomers such as 16:0/13-HpODE PC and 16:0/9-HpODE PC. Sodiated PCOOH ([M+Na](+), m/z 812) provided not only a known product ion (m/z 147) but also characteristic product ions (m/z 541 for 16:0/13-HpODE PC and m/z 388 for 16:0/9-HpODE PC). Thus, three multiple reaction monitorings (MRMs) could be performed. MRM (812/147) enabled determination of 16:0/HpODE PC, and MRM (812/541) and MRM (812/388) allowed specific measurement of 16:0/13-HpODE PC and 16:0/9-HpODE PC, respectively. By using this method, we could determine plasma PCOOH concentrations in healthy subjects and patients with angiographically significant stenosis. In healthy subject and patient plasma, the concentration of 16:0/HpODE PC was close to the sum of the concentrations of 16:0/13-HpODE PC and 16:0/9-HpODE PC. This finding shows that radical and/or enzymatic oxidation, rather than singlet oxygen oxidation, is recognized to cause peroxidation of PC. The newly developed LC-MS/MS method appears to be a powerful tool for developing a better understanding of in vivo lipid peroxidation and its involvement in human diseases. (C) 2014 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.ab.2014.10.017
• 作为产物：
  描述：

  亚油酸甲酯 在 air 作用下， 反应 24.0h， 生成 10,12-Octadecadienoic acid, 9-hydroperoxy-, methyl ester, (E,E)-
  参考文献：
  名称：

  Liquid chromatography–tandem mass spectrometry determination of human plasma 1-palmitoyl-2-hydroperoxyoctadecadienoyl-phosphatidylcholine isomers via promotion of sodium adduct formation

  摘要：

  Accumulation of phosphatidylcholine hydroperoxide (PCOOH), a primary oxidation product of phosphatidylcholine, in blood plasma has been observed in various pathological conditions, including atherosclerosis. In this study, we investigated the use of liquid chromatography-tandem mass spectrometry (LC-MS/MS) to develop a method for accurate quantification of PCOOH (1-palmitoyl-2-hydroperoxy-octadecadienoyl-sn-glycero-3-phosphocholine, 16:0/HpODE PC), focusing on isomers such as 16:0/13-HpODE PC and 16:0/9-HpODE PC. Sodiated PCOOH ([M+Na](+), m/z 812) provided not only a known product ion (m/z 147) but also characteristic product ions (m/z 541 for 16:0/13-HpODE PC and m/z 388 for 16:0/9-HpODE PC). Thus, three multiple reaction monitorings (MRMs) could be performed. MRM (812/147) enabled determination of 16:0/HpODE PC, and MRM (812/541) and MRM (812/388) allowed specific measurement of 16:0/13-HpODE PC and 16:0/9-HpODE PC, respectively. By using this method, we could determine plasma PCOOH concentrations in healthy subjects and patients with angiographically significant stenosis. In healthy subject and patient plasma, the concentration of 16:0/HpODE PC was close to the sum of the concentrations of 16:0/13-HpODE PC and 16:0/9-HpODE PC. This finding shows that radical and/or enzymatic oxidation, rather than singlet oxygen oxidation, is recognized to cause peroxidation of PC. The newly developed LC-MS/MS method appears to be a powerful tool for developing a better understanding of in vivo lipid peroxidation and its involvement in human diseases. (C) 2014 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.ab.2014.10.017

文献信息

• Structure and stereochemistry of novel endoperoxides isolated from the sensitized photooxidation of methyl linoleate. Implications for prostaglandin biosynthesis
  作者：Edward D. Mihelich

  DOI：10.1021/ja00543a061

  日期：1980.11