colneleic acid | 39692-44-9

• 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: colneleic acid
• 英文别名: Colneleinsaeure；9-Nona-1,3-dienoxynon-8-enoic acid
• CAS: 39692-44-9
• 化学式: C₁₈H₃₀O₃
• 分子量: 294.434
• InChiKey: HHZKKFXQEIBVEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  21
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (9S,10E,12Z)-9-(氢过氧基)-10,12-十八碳二烯酸 在 recombinant tobacco divinyl ether synthase 作用下， 以 aq. phosphate buffer 为溶剂， 反应 0.25h， 生成 colneleic acid
  参考文献：
  名称：

  Thermal conversions of fatty acid peroxides to cyclopentenones: A biomimetic model for allene oxide synthase pathway

  摘要：

  The trimethylsilyl (TMS) peroxides of linoleic acid 9(S)-hydroperoxide (TMS or Me esters) were subjected to gas chromatography-mass spectrometry (GC-MS) analyses. The cyclopentenones, trans- and cis-10-oxo-11-phytoenoic acid (10-oxo-PEA, Me or TMS esters) were first time detected as the products of TMS-peroxide thermal conversions. The major products were ketodienes, epoxyalcohols, hemiacetals and decadienals. For further study of thermal cyclopentenone formation, 9(S)- or 13(S)-hydroperoxides of linoleic acid (Me esters) were sealed in ampoules and heated at 230 degrees C for 15 or 30 min. The products were separated by HPLC. The cyclopentenone fractions were collected and analyzed by GC-MS. Trans-10-oxo-PEA (Me) and 10-oxo-9(13)-PEA (Me) were formed during the thermal conversion of 9-hydroperoxide (Me ester). Similarly, the cyclopentenones trans-12-oxo-PEA (Me) and 12-oxo-9(13)-PEA (Me) were detected after the heating of 13-hydroperoxide (Me ester). Thermal formation of cyclopentenones can be considered as a biomimetic model of AOS pathway, providing new insights into the mechanisms of allene oxide formation and cyclization. (C) 2013 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2013.08.005