1,3-dicapryloyl-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-dicapryloyl-2-docosahexaenoylglycerol
• 英文别名: 1,3-di(octanoyloxy)propan-2-yl (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoate
• 化学式: C₄₁H₆₆O₆
• 分子量: 654.971
• InChiKey: KXHQGLFNDKFRQZ-FJALUKDJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.3
• 重原子数：
  47
• 可旋转键数：
  34
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.63
• 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：

  辛酸乙烯酯 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-dicapryloyl-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。
• Synthesis of reversed structured triacylglycerols possessing EPA and DHA at their terminal positions
  作者：Anna V. Gudmundsdottir、Kai-Anders Hansen、Carlos D. Magnusson、Gudmundur G. Haraldsson

  DOI：10.1016/j.tet.2015.09.034

  日期：2015.11

  EPA or DHA activated as acetoxime esters exclusively into the 1,3-positions of glycerol. The saturated fatty acyl groups were subsequently introduced to the remaining 2-position by EDCI coupling agent to accomplish the title compounds highly efficiently. This is the first report on reversed structured TAGs possessing the long-chain n-3 polyunsaturated fatty acids. It is anticipated that these novel

  本报告描述了LML型的反转结构的三酰基甘油（标签）的合成，具有纯EPA或DHA位于与纯偶数沿甘油骨架的终端1,3位饱和脂肪酸（C6：0-C16：0 ）占据2位。这些化合物通过包括高度选择性固定化的两步化学酶促合成路线合成南极假丝酵母脂肪酶掺入EPA或DHA激活为丙酮肟酯专门为甘油的1,3-位置。随后通过EDCI偶联剂将饱和的脂肪酰基引入剩余的2-位，以高效地完成标题化合物。这是具有上的长链n-3多不饱和脂肪酸的结构颠倒的标签的第一份报告。可以预期的是，这些新的化合物和它们的合成方法将找到的各种重要的用途，例如分析标准，筛选生物活性和在作为前药制药领域。
• Utilization of reaction medium-dependent regiospecificity of Candida antarctica lipase (Novozym 435) for the synthesis of 1,3-dicapryloyl-2-docosahexaenoyl (or eicosapentaenoyl) glycerol
  作者：Roxana Irimescu、Kiyomi Furihata、Kazuhiko Hata、Yugo Iwasaki、Tsuneo Yamane

  DOI：10.1007/s11746-001-0258-3

  日期：2001.3

  AbstractA highly efficient enzymatic method for the synthesis of regioisomerically pure 1,3‐dicapryloyl‐2‐docosahexaenoyl glycerol (CDC) in two steps was established. 2‐Monoglyceride (2‐MG) formation by ethanolysis of tridocosahexaenoylglycerol (DDD) with immobilized Candida antarctica lipase (Novozym 435) as catalyst was the key step of the synthesis. CDC was finally obtained by reesterification of 2‐MG with ethylcaprylate (EtC) catalyzed by Rhizomucor miehei lipase (Lipozyme IM). The regiospecificity of Novozym 435 depended on the type of reaction and the initial composition of the reaction medium. It displayed strict 1,3‐regiospecificity for ethanolysis at a high excess of ethanol in the reaction mixture although it displayed no regiospecificity in transesterification and esterification reactions. The highest yield of CDC (85.4%) was obtained by ethanolysis at a 4∶1 weight ratio of ethanol/DDD for 6 h followed by reesterification at a 20∶1 molar ratio of EtC/initial DDD for 1.5 h. The regioisomeric purity of CDC was 100%. Good results were obtained also for the synthesis of 1,3‐dicapryloyl‐eicosapentaenoylglycerol (CEC) by the same method: 84.2% yield and 99.8% regioisomeric purity at the same reactant ratios as above. The yield of the reesterification step and the regioisomeric purity of the product were influenced by the molar ratio of the reactants for both CDC and CEC syntheses: higher excess of EtC favored higher yields and regioisomeric purity of the products.