9(S)-HPODE | 5502-91-0

• 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: 9(S)-HPODE
• 英文别名: 9(R)-HPODE(1-)；(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoic acid；9-hydroperoxyoctadeca-11,12-dienoic acid；(±)9-HpODE；9-hydroperoxy-10,12-octadecadienoic acid；(12Z)-9-hydroperoxy-10,12-octadecandienoic acid
• CAS: 5502-91-0；7324-20-1；26911-36-4；28396-96-5；29774-12-7；39692-45-0；63121-49-3；65941-74-4；67597-24-4；90760-93-3；100018-30-2；104759-96-8；122046-44-0；123410-63-9
• 化学式: C₁₈H₃₂O₄
• 分子量: 312.45
• InChiKey: JGUNZIWGNMQSBM-ZHWJBWRLSA-N

物化性质

• 沸点：
  447.7±38.0 °C(Predicted)
• 密度：
  1.002±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.35
• 重原子数：
  22.0
• 可旋转键数：
  15.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  66.76
• 氢给体数：
  2.0
• 氢受体数：
  3.0

安全信息

• 海关编码：
  2918990090

反应信息

• 作为反应物：
  描述：

  溶血磷脂酰胆碱(鸡蛋) 、 9(S)-HPODE 在 2-甲氧基丙烯 、 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 氯仿 为溶剂， 反应 24.0h， 生成 1-palmitoyl-2-(9-hydroperoxyoctadecadienoyl)-sn-glycero-3-phosphocholine
  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：

  sodium linoleate 在 potato tuber lipoxygenase 作用下， 生成 9(S)-HPODE
  参考文献：
  名称：

  Characterisation of lipoxygenase isoforms from olive callus cultures

  摘要：

  Two lipoxygenase isoforms from olive callus cultures were separated from each other. Acetone powders were made to stabilise activity and remove lipids. Separation was then achieved by salt precipitation and ion-exchange chromatography. Both isoforms had comparable activity with linoleic and alpha-linolenic acid substrates, a basic pH optimum and had molecular masses of around 95 kDa. The callus extracts preferentially formed the 13-hydroperoxy products, in keeping with the pattern of volatile derivatives found in olive tissues and oils derived therefrom. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2008.08.001

文献信息

• Unified mechanism for polyunsaturated fatty acid autoxidation. Competition of peroxy radical hydrogen atom abstraction, .beta.-scission, and cyclization
  作者：Ned A. Porter、Laura S. Lehman、Bruce A. Weber、Karl J. Smith

  DOI：10.1021/ja00411a032

  日期：1981.10