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: 1,2-dicapryloyl-3-eicosapentaenoylglycerol；2,3-di(octanoyloxy)propyl (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoate
• 化学式: C₃₉H₆₄O₆
• 分子量: 628.934
• InChiKey: XUGCSOFEPRRFDH-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：

  辛酸乙酯 、 1,2,3-三(二十碳五烯酰基)甘油 在 Novozym 435 、 Lipozyme-IM 乙醇 作用下， 反应 3.0h， 以84.2%的产率得到1,3-dicapryloyl-2-eicosapentaenoylglycerol
  参考文献：
  名称：

  利用反应介质依赖性南极假丝酵母脂肪酶（Novozym 435）的区域特异性合成1,3-二辛基酰基-2-十二碳六烯酰基（或二十碳五烯酰基）甘油

  摘要：

  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.

  DOI：

  10.1007/s11746-001-0258-3

文献信息

• 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.
• 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.