1,2-di(icosapentaenoyl)glyceride

• 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: 1,2-di(icosapentaenoyl)glyceride
• 英文别名: [3-hydroxy-2-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyl]oxypropyl] (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoate
• 化学式: C₄₃H₆₄O₅
• 分子量: 660.978
• InChiKey: JHFHIXGYPUDQSZ-LPEZNXMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11
• 重原子数：
  48
• 可旋转键数：
  32
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  花生四烯酸 、 1,2-di(icosapentaenoyl)glyceride 在 4-二甲氨基吡啶 、 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 15.0h， 以45 mg的产率得到2,3-bis[[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyl]oxy]propyl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate
  参考文献：
  名称：

  Temperature dependence of production of structured triacylglycerols in the alga Trachydiscus minutus

  摘要：

  This study describes the identification of regioisomers and enantiomers of triacylglycerols of C20 polyunsaturated fatty acids (PUFAs) in the alga Trachydiscus minutus cultivated at different temperatures using reversed- and chiral-phase liquid chromatography-mass spectrometry. The use of the two different phases contributes to ready identification, both qualitative and semiquantitative, of regioisomers and enantiomers of triacylglycerols containing eicosapentaenoic and arachidonic in the molecule. The ratio of regioisomers and enantiomers of triacylglycerols (TAG) depends on the temperature of cultivation; with lowering temperature the proportion of the achiral TAG increases and the enantiomer ratio diverges from 1:1. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2014.12.013
• 作为产物：
  描述：

  1,2-dieicosapentanoylglycero-3-phophocholine 在 phospholipase C from Clostridium perfringens (Clostridium welchii) Type I 作用下， 以 乙醚 为溶剂， 反应 3.0h， 生成 1,2-di(icosapentaenoyl)glyceride
  参考文献：
  名称：

  Temperature dependence of production of structured triacylglycerols in the alga Trachydiscus minutus

  摘要：

  This study describes the identification of regioisomers and enantiomers of triacylglycerols of C20 polyunsaturated fatty acids (PUFAs) in the alga Trachydiscus minutus cultivated at different temperatures using reversed- and chiral-phase liquid chromatography-mass spectrometry. The use of the two different phases contributes to ready identification, both qualitative and semiquantitative, of regioisomers and enantiomers of triacylglycerols containing eicosapentaenoic and arachidonic in the molecule. The ratio of regioisomers and enantiomers of triacylglycerols (TAG) depends on the temperature of cultivation; with lowering temperature the proportion of the achiral TAG increases and the enantiomer ratio diverges from 1:1. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2014.12.013

文献信息

• The synthesis of homogeneous triglycerides of eicosapentaenoic acid and docosahexaenoic acid by lipase
  作者：Gudmundur G. Haraldsson、Birgir Ö. Gudmundsson、Örn Almarsson

  DOI：10.1016/0040-4020(94)00983-2

  日期：1995.1

  highly efficient synthesis of homogeneous triglycerides of either pure eicosapentaenoic acid, 1, or docosahexaenoic acid, 2, by an immobilized non-regiospecific yeast lipase from Candida antarctica is described. Two methods were used: Interesterification of tributyrin and direct esterification of glycerol with stoichiometric amount of 99 % EPA or DHA as ethyl esters and free fatty acids, respectively

  通过固定化的南极假丝酵母的非区域特异性酵母脂肪酶高效合成纯二十碳五烯酸1或二十二碳六烯酸2的均质甘油三酸酯描述。使用了两种方法：三丁酸甘油酯的酯交换和分别以化学计量的99％EPA或DHA的乙基酯和游离脂肪酸的甘油直接酯化。两种方法均在真空下于65°C且无任何溶剂的条件下进行。将挥发性副产物冷凝到冷却的阱中，从而使平衡朝着完成方向移动。在所有情况下，都可以在不到72小时的时间内完成完全掺入，但是发现直接酯化比酯交换要快得多，这两个过程都涉及EPA和DHA。高场11 H NMR光谱分析提供了在直接酯化反应过程中对中间甘油酯的详细研究。以优异的产率提供的所得粗产物的纯度非常高。
• 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.