| 1360110-38-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• CAS: 1360110-38-8
• 化学式: C₂₁H₃₂O₂
• 分子量: 316.484
• InChiKey: QWDCYFDDFPWISL-LLKFSHQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.08
• 重原子数：
  23.0
• 可旋转键数：
  13.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  二十碳五烯酸甲酯 在 二甲基二环氧乙烷 、 吡啶 、 二溴三苯基膦 、 溶剂黄146 、 锌 作用下， 以 丙酮 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 、 (5Z,8Z,11Z,14Z,17E)-eicosa-5,8,11,14,17-pentaenoic acid methyl ester
  参考文献：
  名称：

  Trans Fatty Acids: Chemical Synthesis of Eicosapentaenoic Acid Isomers and Detection in Rats Fed a Deodorized Fish Oil Diet

  摘要：

  Eicosapentaenoic acid (EPA) is a polyunsaturated fatty acid present in fish oils used for omega-3 enriched diets. The natural cis double bond geometry can be transformed to the trans configuration during the deodorization process utilized in the food industry. The analytical discrimination of the possible five monotrans regioisomers represents a limiting step for the recognition and structure-activity relationship in connection with the harmful effects of trans fatty acids in health. We carried out a dual synthetic strategy, providing new access to monotrans EPA isomers and valuable information on GC and NMR characteristics for further applications in metabolomics and lipidomics. This small library was used as an analytical reference for isomer determination in deodorized fish oils and the follow-up of rats fed fish oil diets, evidencing for the first time that monotrans EPA isomers are incorporated in liver mitochondrial membranes after dietary intake.

  DOI：

  10.1021/tx200467c