1-docosahexaenoyl-2,3-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: 1-docosahexaenoyl-2,3-distearylglycerol
• 英文别名: 2,3-di(octadecanoyloxy)propyl (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoate
• 化学式: C₆₁H₁₀₆O₆
• 分子量: 935.509
• InChiKey: BFXHBMAQQCDBSZ-ATWGOFEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  23.2
• 重原子数：
  67
• 可旋转键数：
  54
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  二十二碳六烯酸 、 三硬脂酸甘油酯 在 Rhizomocur miehei lipase (Lipozome^TM) 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以28%的产率得到1-docosahexaenoyl-2,3-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

• Chemoenzymatic synthesis of structured triacylglycerols containing eicosapentaenoic and docosahexaenoic acids
  作者：Gudmundur G. Haraldsson、Arnar Halldorsson、Elin Kuls

  DOI：10.1007/s11746-000-0179-1

  日期：2000.11

  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).