11-hydroperoxy9Z-octadecenoic acid | 67851-50-7

• 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: 11-hydroperoxy9Z-octadecenoic acid
• 英文别名: (Z)-11-hydroperoxyoctadec-9-enoic acid
• CAS: 67851-50-7
• 化学式: C₁₈H₃₄O₄
• 分子量: 314.466
• InChiKey: WWEFPLFGKQOHPE-QINSGFPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  22
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  油酸 在 N-羟基邻苯二甲酰亚胺 、 ammonium cerium (IV) nitrate 、 氧气 、 天然维生素E 作用下， 以 乙醇 、 乙腈 为溶剂， 生成 (10S)-hydroperoxy-(8E)-octadecenoic acid 、 11-hydroperoxy9Z-octadecenoic acid 、 、 (8R)-hydroperoxyoleic acid 、 (R,E)-10-hydroperoxyoctadec-8-enoic acid 、 (S,E)-9-hydroperoxyoctadec-10-enoic acid 、 (R,E)-9-hydroperoxyoctadec-10-enoic acid
  参考文献：
  名称：

  Stereoselective oxidation of regioisomeric octadecenoic acids by fatty acid dioxygenases

  摘要：

  Seven Z-octadecenoic acids having the double bond located in positions 6Z to 13Z were photooxidized. The resulting hydroperoxy-E-octadecenoic acids [HpOME(E)] were resolved by chiral phase-HPLC-MS, and the absolute configurations of the enantiomers were determined by gas chromatographic analysis of diastereoisomeric derivatives. The MS/MS/MS spectra showed characteristic fragments, which were influenced by the distance between the hydroperoxide and carboxyl groups. These fatty acids were then investigated as substrates of cyclooxygenase-1 (COX-1), manganese lipoxygenase (MnLOX), and the (8R)-dioxygenase (8R-DOX) activities of two linoleate diol synthases (LDS) and 10R-DOX. COX-1 and MnLOX abstracted hydrogen at C-11 of (12Z)-18:1 and C-12 of (13Z)-18:1. (11Z)-18:1 was subject to hydrogen abstraction at C-10 by MnLOX and at both allylic positions by COX-1. Both allylic hydrogens of (8Z)-18:1 were also abstracted by 8R-DOX activities of LDS and 10R-DOX, but only the allylic hydrogens close to the carboxyl groups of (11Z)-18:1 and (12Z)-18:1. 8R-DOX also oxidized monoenoic C-14-C-20 fatty acids with double bonds at the (9Z) position, suggesting that the length of the omega end has little influence on positioning for oxygenation. We conclude that COX-1 and MnLOX can readily abstract allylic hydrogens of octadecenoic fatty acids from C-10 to C-12 and 8R-DOX from C-7 and C-12.-Oliw, E. H., A. Wennman, I. Hoffmann, U. Garscha, M. Hamberg, and F. Jerneren. Stereoselective oxidation of regioisomeric octadecenoic acids by fatty acid dioxygenases. J. Lipid Res. 2011. 52: 1995-2004.

  DOI：

  10.1194/jlr.m018259

文献信息

• Stereoselective oxidation of regioisomeric octadecenoic acids by fatty acid dioxygenases
  作者：Ernst H. Oliw、Anneli Wennman、Inga Hoffmann、Ulrike Garscha、Mats Hamberg、Fredrik Jernerén

  DOI：10.1194/jlr.m018259

  日期：2011.11

  Seven Z-octadecenoic acids having the double bond located in positions 6Z to 13Z were photooxidized. The resulting hydroperoxy-E-octadecenoic acids [HpOME(E)] were resolved by chiral phase-HPLC-MS, and the absolute configurations of the enantiomers were determined by gas chromatographic analysis of diastereoisomeric derivatives. The MS/MS/MS spectra showed characteristic fragments, which were influenced by the distance between the hydroperoxide and carboxyl groups. These fatty acids were then investigated as substrates of cyclooxygenase-1 (COX-1), manganese lipoxygenase (MnLOX), and the (8R)-dioxygenase (8R-DOX) activities of two linoleate diol synthases (LDS) and 10R-DOX. COX-1 and MnLOX abstracted hydrogen at C-11 of (12Z)-18:1 and C-12 of (13Z)-18:1. (11Z)-18:1 was subject to hydrogen abstraction at C-10 by MnLOX and at both allylic positions by COX-1. Both allylic hydrogens of (8Z)-18:1 were also abstracted by 8R-DOX activities of LDS and 10R-DOX, but only the allylic hydrogens close to the carboxyl groups of (11Z)-18:1 and (12Z)-18:1. 8R-DOX also oxidized monoenoic C-14-C-20 fatty acids with double bonds at the (9Z) position, suggesting that the length of the omega end has little influence on positioning for oxygenation. We conclude that COX-1 and MnLOX can readily abstract allylic hydrogens of octadecenoic fatty acids from C-10 to C-12 and 8R-DOX from C-7 and C-12.-Oliw, E. H., A. Wennman, I. Hoffmann, U. Garscha, M. Hamberg, and F. Jerneren. Stereoselective oxidation of regioisomeric octadecenoic acids by fatty acid dioxygenases. J. Lipid Res. 2011. 52: 1995-2004.