trans-12-oxo-10-phytoenoic acid methyl ester | 1014394-92-3

• 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: trans-12-oxo-10-phytoenoic acid methyl ester
• CAS: 1014394-92-3
• 化学式: C₁₉H₃₂O₃
• 分子量: 308.461
• InChiKey: GQJPWZJTWPPQJW-DLBZAZTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.84
• 重原子数：
  22.0
• 可旋转键数：
  12.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  (9Z,11E,13S)-12,13-epoxy-9,11-octadecadienoic acid methyl ester 以 正己烷 为溶剂， 生成 、 trans-12-oxo-10-phytoenoic acid methyl ester 、 13-hydroxy-12-oxo-octadec-cis-9-enoic acid methyl ester
  参考文献：
  名称：

  Cyclization of natural allene oxide in aprotic solvent: formation of the novel oxylipin methyl cis-12-oxo-10-phytoenoate

  摘要：

  Allene oxide, (9Z, I I F)-12,13-epoxy-9,11-octadecadienoic acid (12,13-EOD), was prepared by incubation of linoleic acid (13S)-hydroperoxide with flaxseed allene oxide synthase (AOS) and purified (as methyl ester) by low temperature HPLC. Identification of pure 12,13-EOD was substantiated by its UV and H-1 NMR spectra and by GC-MS data for its methanol trapping product. The methyl ester of 12,13-EOD (but not the free carboxylic acid) is slowly cyclized in hexane solution, affording a novel cyclopentenone cis- 12-oxo-10-phytoenoic acid. Free carboxylic form of 12,13-EOD does not cyclize due to the exceeding formation of macrolactone (9Z)-12-oxo-9-octadecen-11-olide. The spontaneous cyclization of pure natural allene oxide (12,13-EOD) into cis-cyclopentenone have been observed first time. (c) 2007 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2007.04.010