(4Z,7Z,10Z,13Z,16Z,19Z)-Docosa-4,7,10,13,16,19-hexaenoic acid 2-tetradecanoyloxy-1-tetradecanoyloxymethyl-ethyl ester

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: (4Z,7Z,10Z,13Z,16Z,19Z)-Docosa-4,7,10,13,16,19-hexaenoic acid 2-tetradecanoyloxy-1-tetradecanoyloxymethyl-ethyl ester
• 英文别名: 1-Myristoyl-2-docosahexaenoyl-3-myristoyl-glycerol；1,3-di(tetradecanoyloxy)propan-2-yl (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoate
• 化学式: C₅₃H₉₀O₆
• 分子量: 823.294
• InChiKey: MOJPINCPRSTPNA-OJMUMCIQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  18.8
• 重原子数：
  59
• 可旋转键数：
  46
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  肉豆蔻酸乙烯酯 在 4-二甲氨基吡啶 、 immobilized Candida antarctica lipase 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 生成 (4Z,7Z,10Z,13Z,16Z,19Z)-Docosa-4,7,10,13,16,19-hexaenoic acid 2-tetradecanoyloxy-1-tetradecanoyloxymethyl-ethyl ester
  参考文献：
  名称：

  Chemoenzymatic synthesis of structured triacylglycerols by highly regioselective acylation

  摘要：

  A highly efficient two-step chemoenzymatic synthesis of structured triacylglycerols comprising a pure n-3 polyunsaturated fatty acid at the mid-position and a pure saturated fatty acid located at the end-positions is described. In the first step an immobilized Candida antarctica lipase was observed to display an excellent regioselectivity toward the end-positions of glycerol at 0-4degreesC using vinyl esters as acylating agents. The n-3 fatty acids were introduced into the remaining mid-position highly efficient and in excellent yields using EDCI coupling agent. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.09.059

文献信息

• Chemoenzymatic synthesis of structured triacylglycerols by highly regioselective acylation
  作者：Arnar Halldorsson、Carlos D Magnusson、Gudmundur G Haraldsson

  DOI：10.1016/j.tet.2003.09.059

  日期：2003.11

  A highly efficient two-step chemoenzymatic synthesis of structured triacylglycerols comprising a pure n-3 polyunsaturated fatty acid at the mid-position and a pure saturated fatty acid located at the end-positions is described. In the first step an immobilized Candida antarctica lipase was observed to display an excellent regioselectivity toward the end-positions of glycerol at 0-4degreesC using vinyl esters as acylating agents. The n-3 fatty acids were introduced into the remaining mid-position highly efficient and in excellent yields using EDCI coupling agent. (C) 2003 Elsevier Ltd. All rights reserved.