1,3-dilauroyl-2-docosahexaenoylglycerol

• 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-docosahexaenoylglycerol
• 英文别名: 1,3-di(dodecanoyloxy)propan-2-yl (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoate
• 化学式: C₄₉H₈₂O₆
• 分子量: 767.186
• InChiKey: KAOUKXOHEQNHSA-LVJOZRDRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.7
• 重原子数：
  55
• 可旋转键数：
  42
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 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-docosahexaenoylglycerol
  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。
• Chemical synthesis and NMR characterization of structured polyunsaturated triacylglycerols
  作者：Laëtitia Fauconnot、Fabien Robert、Renaud Villard、Fabiola Dionisi

  DOI：10.1016/j.chemphyslip.2005.11.004

  日期：2006.2

  The chemical synthesis of pure triacylglycerol (TAG) regioisomers, that contain long chain polyunsaturated fatty acids, such as arachidonic acid (AA) or docosahexaenoic acid (DHA), and saturated fatty acids, Such as lauric acid (La) or palmitic acid (P), at defined positions, is described. A single step methodology using (benzotriazol-1-yloxy)-tripyrrolidinophosphonium hexafluorophosphate (PyBOP), an activator of carboxyl group commonly used in peptide synthesis and occasionally used in carboxylic acid esterification, has been developed for structured TAG synthesis. Identification of the fatty acyl chains for each TAG species was confirmed by atmospheric pressure chemical ionisation mass spectrometry (APCI-MS) and fatty acid positional distribution was determined by H-1 and C-13 NMR spectra. The generic described procedures can be applied to a large variety Of Substrates and was used for the production of specific triacylglycerols of defined molecular structures, with high regioisomeric purity. Combination of MS and NMR was shown to be an efficient tool for structural analysis of TAG. In particular. some NMR signals were demonstrated to be regioisomer specific, allowing rapid positional analysis of LC-PUFA containing TAG. (C) 2005 Elsevier Ireland Ltd. All rights reserved.
• 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.