1,3-dicapryloyl-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-dicapryloyl-2-eicosapentaenoylglycerol
• 英文别名: 1,3-di(octanoyloxy)propan-2-yl (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoate
• 化学式: C₃₉H₆₄O₆
• 分子量: 628.934
• InChiKey: CTXRCGJUJXPDOP-SWWMJBKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.8
• 重原子数：
  45
• 可旋转键数：
  33
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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-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。
• Enzymatic synthesis of symmetrical 1,3-diacylglycerols by direct esterification of glycerol in solvent-free system
  作者：Roxana Rosu、Mamoru Yasui、Yugo Iwasaki、Tsuneo Yamane

  DOI：10.1007/s11746-999-0074-7

  日期：1999.7

  Abstract1,3‐Diacylglycerols were synthesized by direct esterification of glycerol with free fatty acids in a solvent‐free system. Free fatty acids with relatively low melting points (<45°C) such as unsaturated and medium‐chain saturated fatty acids were used. With stoichiometric ratios of the reactants and water removal by evaporation at 3 mm Hg vacuum applied at 1 h and thereafter, the maximal 1,3‐diacylglycerol content in the reaction mixture was: 84.6% for 1,3‐dicaprylin, 84.4% for 1,3‐dicaprin, 74.3% for 1,3‐dilinolein, 71.7% for 1,3‐dieicosapentaenoin, 67.4% for 1,3‐dilaurin, and 61.1% for 1,3‐diolein. Some of the system's parameters (temperature, water removal, and molar ratio of the reactants) were optimized for the production of 1,3‐dicaprylin, and the maximal yield reached 98%. The product was used for the chemical synthesis of 1,3‐dicapryloyl‐2‐eicosapentaenoylglycerol. The yield after purification was 42%, and the purity of the triacylglycerol was 98% (both 1,3‐dicapryloyl‐2‐eicosapentaenoylglycerol and 1,2‐dicapryloyl‐3‐eicosapentaenoylglycerol included) by gas chromatographic analysis, of which 90% was the desired structured triacylglycerol (1,3‐dicapryloyl‐2‐eicosapentaenoylglycerol) as determined by silver ion high‐performance liquid chromatographic analysis.
• Enzymatic synthesis of 1,3-dicapryloyl-2-eicosapentaenoylglycerol
  作者：Roxana Irimescu、Mamoru Yasui、Yugo Iwasaki、Nobuyoshi Shimidzu、Tsuneo Yamane

  DOI：10.1007/s11746-000-0080-y

  日期：2000.5

  Abstract1,3‐Dicapryloyl‐2‐eicosapentaenoylglycerol (CEC) was synthesized by interesterification of trieicosapentaenoylglycerol (EEE) with ethyl caprylate (EtC) catalyzed by LipozymeTM. After some of the reaction conditions were optimized, the maximal molar content of CEC in the glycerides of the reaction mixture was 91%. Among the parameters studied in the optimization, the critical ones were: (i) the water content, which influenced the conversion of EEE to CEC and 1‐capryloyl‐2‐eicosapentaenoylglycerol (CEOH), and (ii) the timing of water removal under reduced pressure for the reesterification of CEOH to form CEC. The complete synthesis of CEC from ethyl eicosapentaenoate (EtE) was performed in three steps: (i) hydrolysis of EtE to free eicosapentaenoic acid (EPA), (ii) esterification of glycerol with EPA to form EEE, and (iii) interesterification of EEE with EtC under the optimized conditions. The first two steps were catalyzed by NovozymTM and the third by LipozymeTM. The total yield over all the steps was 88%, and no purification of the intermediates was necessary. The regioisomeric purity of the product was 100% by silver‐ion high‐pressure liquid chromatography.
• Comparison of acyl donors for lipase-catalyzed production of 1,3-dicapryloyl-2-eicosapentaenoylglycerol
  作者：Roxana Irimescu、Kazuhiko Hata、Yugo Iwasaki、Tsuneo Yamane

  DOI：10.1007/s11746-001-0221-3

  日期：2001.1

  AbstractSynthesis of 1,3‐dicapryloyl‐2‐eicosapentaenoylglycerol (CEC) catalyzed by Lipozyme IM (immobilized Rhizomucor miehei lipase) was performed by interesterification of trieicosapentaenoylglycerol (EEE) with caprylic acid (CA) (acidolysis) and EEE with ethyl caprylate (EtC) (interesterification). Both methods involved two steps: (i) transesterification at an optimized water content and temperature for the high yield conversion of the substrate to CEC, 1‐capryloyl‐2‐eicosapentaenoylglycerol (CEOH) and 2‐eicosapentaenoylglycerol (OHEOH), and (ii) reesterification of CEOH and OHEOH to CEC by water removal under reduced pressure. Interesterification had clear advantages over acidolysis. The reaction rates for interesterification were higher and the reaction times shorter. The final yield of CEC by interesterification was higher, and the extent of acyl migration, indicated by the tricapryloylglycerol content, was lower. The disadvantage of the higher price of EtC used for interesterification (approximately 10 times higher than the price of CA) was overcome by synthesizing it directly in the same reaction vessel prior to the interesterification step. EtC was rapidly synthesized by esterification of CA with ethanol in high yield (92% obtained in 2.5 h). The amount of water added to the reaction mixture and the reaction temperature influenced the yields of CEC, CEOH, and OHEOH in the transesterification step for both interesterification and acidolysis methods. The regioisomeric purity of CEC was 100% for both methods at temperatures of 40°C or less. The highest yield of CEC (81%) was obtained for the interesterification of EEE with EtC, formed directly in the same reaction vessel, at a CA/EEE molar ratio of 20∶1 and 30°C.
• 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.