| 1384856-00-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• CAS: 1384856-00-1
• 化学式: C₁₈H₃₂O₃
• 分子量: 296.45
• InChiKey: OAUPTQCGIPIOMR-SDNWHVSQSA-N

反应信息

• 作为产物：
  描述：

  (e)-7-Hydroxy-8-octadecenoic acid 在 戴斯-马丁氧化剂 作用下， 生成
  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