Hepoxilin B3 | 200957-05-7

• 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: Hepoxilin B3
• 英文别名: 10-hydroxy-trans-11(S),12(S)-epoxyeicosa-5(Z),8(Z),14(Z)-trienoic acid；(5Z,8Z)-10-hydroxy-10-[(2S,3S)-3-[(Z)-oct-2-enyl]oxiran-2-yl]deca-5,8-dienoic acid
• CAS: 200957-05-7
• 化学式: C₂₀H₃₂O₄
• 分子量: 336.472
• InChiKey: DWNBPRRXEVJMPO-RNGYDEEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  70.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  12-(S)-过氧化氢-5Z,8Z,10E,14Z-二十碳四烯酸 在 potassium hydrogensulfate 、 hematin 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 0.17h， 生成 Hepoxilin A3 、 Hepoxilin B3
  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

• HEPOXILIN ANALOG ENANTIOMERS
  申请人：Pace-Asciak Cecil

  公开号：US20100210727A1

  公开（公告）日：2010-08-19

  The present invention relates to enantiomeric forms of hepoxilin analogs of Formula I-VIII, pharmaceutical compositions thereof, a method for the separation of said enantiomeric forms of hepoxilin analogs comprising applying said hepoxilin to a chiral phase HPLC column and eluting said hepoxilin with an alkane and alcohol solvent mixture. Said enantiomeric forms of hepoxilin analogs of Formula I-VIII were found to be useful in controlling the biological effects of PPAR mediated transcriptional control for the treatment of diseases such as cancer, thromboxane-mediated diseases and for modulating intracellular calcium concentration.
• US8710252B2
  申请人：——

  公开号：US8710252B2

  公开（公告）日：2014-04-29
• 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.