2-eicosapentaenoyl-1,3-distearylglycerol

• 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: 2-eicosapentaenoyl-1,3-distearylglycerol
• 英文别名: 1,3-stearoyl-2-eicosapentaenoyl-glycerol；S-EPAS；1-Stearoyl-2-eicosapentaenoyl-3-stearoyl-glycerol；1,3-di(octadecanoyloxy)propan-2-yl (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoate
• 化学式: C₅₉H₁₀₄O₆
• 分子量: 909.471
• InChiKey: CBXJYBYDCKGVBG-DAWAMIFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  22.6
• 重原子数：
  65
• 可旋转键数：
  53
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 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：

  EPA乙酯 在 4-二甲氨基吡啶 、 sodium hydroxide 、 edetate disodium 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 26.0h， 生成 2-eicosapentaenoyl-1,3-distearylglycerol
  参考文献：
  名称：

  化学酶促合成含二十碳五烯酸和二十二碳六烯酸的结构化三酰基甘油

  摘要：

  AbstractThere are indications in the recent literature that the location of polyunsaturated fatty acids, such as eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA), in triacylglycerols (TAG) may influence their oxidative stability. To address that question, two types of structured lipids were designed and synthesized: firstly, a TAG molecule possessing pure EPA or DHA at the mid‐position with stearic acid at the outer positions; and secondly, a TAG molecule possessing pure EPA or DHA located at one of the outer positions with stearic acid at the mid‐position and the remaining end position. The former adduct was synthesized in two steps by a chemoenzymatic approach. In the first step 1,3‐distearolyglycerol was afforded in good yield (74%) by esterifying glycerol with two equivalents of stearic acid in ether in the presence of silica gel using LipozymeTM as a biocatalyst. This was followed by a subsequent chemical esterification with pure EPA or DHA using 1‐(3‐dimethylaminopropyl)‐3‐ethylcarbodiimide as a coupling agent in the presence of 4‐dimethylaminopyridine in dichloromethane in excellent yields (94 and 91, respectively). The latter adduct was synthesized in two enzymatic steps. In the first step tristearoylglycerol was prepared in very high yield (88%) by esterifying glycerol with a stoichiometric amount of stearic acid under vacuum at 70–75°C using an immobilized Candida antarctica lipase without a solvent. That adduct was subsequently treated in an acidolysis reaction with two equivalents of EPA or DHA without solvent at 70–75°C or in toluene at 40°C in the presence of Lipozyme to afford the desired product in moderate yields (44 and 29%, respectively).

  DOI：

  10.1007/s11746-000-0179-1

文献信息

• Autoxidation of synthetic isomers of triacylglycerol containing eicosapentaenoic acid
  作者：Yasushi Endo、Sanae Hoshizaki、Kenshiro Fujimoto

  DOI：10.1007/s11746-997-0178-x

  日期：1997.5

  AbstractSeveral triacylglycerols (TAG) that contained eicosapentaenoic acid (EPA) were chemically synthesized and stored at 25°C to assess the influence of TAG structure on oxidative stability and formation of oxidation products. Oxidative stability was evaluated by oxygen consumption during storage of the TAG. Autoxidation products of TAG were analyzed by high‐performance liquid chromatography (HPLC) and liquid chromatography‐mass spectrometry (LC‐MS). Results showed that a 2:1 (mole/mole) mixture of trieicosapentaenoylglycerol (EEE) and tripalmitoylglycerol (PPP) was most susceptible to autoxidation. The oxidative stability of TAG that contained EPA and palmitic acid was negatively correlated with the moles of EPA in a single TAG molecule. When TAG with one EPA and two other fatty acids were oxidized, chainlength of constituent fatty acids hardly affected the oxidative stability of EPA‐containing TAG molecules, except for stearic acid. HPLC and LC‐MS analyses showed that monohydroperoxides were major oxidation products regardless of type of TAG. Bis‐ and tris‐hydroperoxides were formed during autoxidation of EEE and dieicos‐apentaenoylpalmitoylglycerol. Monohydroperoxy epidioxides were found in all autoxidized TAG. These observations suggested that TAG structure affected the oxidation of TAG with highly unsaturated fatty acids.