12(R)-hydroperoxyeicosa-5(Z),8(Z),10(E),14(Z)-tetraenoic acid | 126873-49-2

• 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: 12(R)-hydroperoxyeicosa-5(Z),8(Z),10(E),14(Z)-tetraenoic acid
• 英文别名: 12R-HPETE；12(R)-Hpete；(5Z,8Z,10E,12R,14Z)-12-hydroperoxyicosa-5,8,10,14-tetraenoic acid
• CAS: 126873-49-2
• 化学式: C₂₀H₃₂O₄
• 分子量: 336.472
• InChiKey: ZIOZYRSDNLNNNJ-ZYBDYUKJSA-N

物化性质

• 沸点：
  518.0±50.0 °C(Predicted)
• 密度：
  1.013±0.06 g/cm3(Predicted)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  24
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  花生四烯酸 在 氧气 、 天然维生素E 作用下， 以 正己烷 、 异丙醇 为溶剂， 反应 36.0h， 生成 12(R)-hydroperoxyeicosa-5(Z),8(Z),10(E),14(Z)-tetraenoic acid
  参考文献：
  名称：

  LC–MS/MS analysis of epoxyalcohols and epoxides of arachidonic acid and their oxygenation by recombinant CYP4F8 and CYP4F22

  摘要：

  CYP4F22 and CYP4F8 are expressed in epidermis, and mutations of CYP4F22 are associated with lamellar ichthyosis. Epoxyalcohols (HEETs) and epoxides (EETs) of 20:4n-6 appear to be important for the water permeability barrier of skin. Our aim was to study the MS/MS spectra and fragmentation of these compounds and to determine whether they were oxidized by CYP4F22 or CYP4F8 expressed in yeast. HEETs were prepared from 1 5-hydroperoxyeicosatetraenoic acid (15-HPETE), 12-HPETE, and their- [H-2(8)]labeled isotopomers, and separated by normal phase-HPLC with MS/MS analysis. CYP4F22 oxygenated 20:4n-6 at C-I 8, whereas metabolites of HEETs could not be identified. CYP4F8 formed omega 3 hydroxy metabolites of HEETs derived from 12R-HPETE with 11,12-epoxy-10-hydroxy configuration, but not HEETs derived from 15S-HPETE. 8,9-EET and 11,12-EET were also subject to omega 3 hydroxylation by CYP4F8. We conclude that CYP4F8 and CYP4F22 oxidize 20:4n-6 and that CYP4F8 selectively oxidizes 8,9-EET, 11,12-EET, and 10, 11R, 12R-HEET at the omega 3 position. (C) 2010 Published by Elsevier Inc.

  DOI：

  10.1016/j.abb.2009.11.013

文献信息

• [EN] METABOLOMICS-BASED IDENTIFICATION OF DISEASE-CAUSING AGENTS<br/>[FR] IDENTIFICATION D'AGENTS PROVOQUANT UNE MALADIE BASÉE SUR LA MÉTABOLOMIQUE
  申请人：GEORGIA TECH RES INST

  公开号：WO2009052186A1

  公开（公告）日：2009-04-23

  A method, computer-readable medium, and system for identifying one or more metabolites associated with a disease, comprising: comparing gene expression data from diseased cells to gene expression data from control cells in order to deduce genes that are differentially-regulated in the diseased cells relative to the control cells; based on enzyme function and pathway data for all human metabolites that utilize the genes that are differentially-regulated in the disease cells, identifying one or more metabolites whose intracellular levels are higher or lower in diseased cells than in control cells, and thereby associating the one or more metabolites with the disease.
• LC–MS/MS analysis of epoxyalcohols and epoxides of arachidonic acid and their oxygenation by recombinant CYP4F8 and CYP4F22
  作者：T. Nilsson、I.V. Ivanov、E.H. Oliw

  DOI：10.1016/j.abb.2009.11.013

  日期：2010.2

  CYP4F22 and CYP4F8 are expressed in epidermis, and mutations of CYP4F22 are associated with lamellar ichthyosis. Epoxyalcohols (HEETs) and epoxides (EETs) of 20:4n-6 appear to be important for the water permeability barrier of skin. Our aim was to study the MS/MS spectra and fragmentation of these compounds and to determine whether they were oxidized by CYP4F22 or CYP4F8 expressed in yeast. HEETs were prepared from 1 5-hydroperoxyeicosatetraenoic acid (15-HPETE), 12-HPETE, and their- [H-2(8)]labeled isotopomers, and separated by normal phase-HPLC with MS/MS analysis. CYP4F22 oxygenated 20:4n-6 at C-I 8, whereas metabolites of HEETs could not be identified. CYP4F8 formed omega 3 hydroxy metabolites of HEETs derived from 12R-HPETE with 11,12-epoxy-10-hydroxy configuration, but not HEETs derived from 15S-HPETE. 8,9-EET and 11,12-EET were also subject to omega 3 hydroxylation by CYP4F8. We conclude that CYP4F8 and CYP4F22 oxidize 20:4n-6 and that CYP4F8 selectively oxidizes 8,9-EET, 11,12-EET, and 10, 11R, 12R-HEET at the omega 3 position. (C) 2010 Published by Elsevier Inc.