1,3-dilauroyl-2-eicosapentaenoylglycerol

• 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: 1,3-dilauroyl-2-eicosapentaenoylglycerol
• 英文别名: 1,3-di(dodecanoyloxy)propan-2-yl (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoate
• 化学式: C₄₇H₈₀O₆
• 分子量: 741.149
• InChiKey: JAKJKGYBGCDGSS-FBSBXCKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.1
• 重原子数：
  53
• 可旋转键数：
  41
• 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：

  月桂酸乙烯酯 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 1,3-dilauroyl-2-eicosapentaenoylglycerol
  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
  作者：Arnar Halldorsson、Carlos D Magnusson、Gudmundur G Haraldsson

  DOI：10.1016/s0040-4039(01)01598-2

  日期：2001.10

  Six regioisomerically pure structured triacylglycerols possessing a medium-chain fatty acid (C8, C10 or C12) at the primary positions and pure eicosapentaenoic acid or docosahexaenoic acid at the secondary position of the glycerol moiety were prepared in two steps by a chemoenzymatic approach using lipase.

  通过化学酶法分两个步骤制备了六种区域异构纯的结构三酰甘油，它们在主要位置具有中链脂肪酸（C 8，C 10或C 12），在次要位置具有纯二十碳五烯酸或二十二碳六烯酸。使用脂肪酶。
• Autoxidation of synthetic isomers of triacylglycerol containing eicosapentaenoic acid
  作者：Yasushi Endo、Sanae Hoshizaki、Kenshiro Fujimoto

  DOI：10.1007/s11746-997-0178-x

  日期：1997.5

  AbstractSeveral triacylglycerols (TAG) that contained eicosapentaenoic acid (EPA) were chemically synthesized and stored at 25°C to assess the influence of TAG structure on oxidative stability and formation of oxidation products. Oxidative stability was evaluated by oxygen consumption during storage of the TAG. Autoxidation products of TAG were analyzed by high‐performance liquid chromatography (HPLC) and liquid chromatography‐mass spectrometry (LC‐MS). Results showed that a 2:1 (mole/mole) mixture of trieicosapentaenoylglycerol (EEE) and tripalmitoylglycerol (PPP) was most susceptible to autoxidation. The oxidative stability of TAG that contained EPA and palmitic acid was negatively correlated with the moles of EPA in a single TAG molecule. When TAG with one EPA and two other fatty acids were oxidized, chainlength of constituent fatty acids hardly affected the oxidative stability of EPA‐containing TAG molecules, except for stearic acid. HPLC and LC‐MS analyses showed that monohydroperoxides were major oxidation products regardless of type of TAG. Bis‐ and tris‐hydroperoxides were formed during autoxidation of EEE and dieicos‐apentaenoylpalmitoylglycerol. Monohydroperoxy epidioxides were found in all autoxidized TAG. These observations suggested that TAG structure affected the oxidation of TAG with highly unsaturated fatty acids.
• 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.