1,3-dipalmitoyl-2-5,8,11,14,17-eicosapentanoyl 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: 1,3-dipalmitoyl-2-5,8,11,14,17-eicosapentanoyl glyceride
• 英文别名: 5Z,8Z,11Z,14Z,17Z-eicosapentaenoic acid, 2-[(1-oxohexadecyl)oxy]-1-[[(1-oxohexadecyl)oxy]methyl]ethyl ester；1,3-di(hexadecanoyloxy)propan-2-yl (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoate
• 化学式: C₅₅H₉₆O₆
• 分子量: 853.364
• InChiKey: CCKKDORBDQDVMQ-PDZACQBISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  20.4
• 重原子数：
  61
• 可旋转键数：
  49
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.76
• 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：

  十六酸乙烯酯 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 15.0h， 生成 1,3-dipalmitoyl-2-5,8,11,14,17-eicosapentanoyl glyceride
  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

• Effect of nitrogen and phosphorus starvation on the polyunsaturated triacylglycerol composition, including positional isomer distribution, in the alga Trachydiscus minutus
  作者：Tomáš Řezanka、Jaromír Lukavský、Linda Nedbalová、Karel Sigler

  DOI：10.1016/j.phytochem.2011.08.017

  日期：2011.12

  those TAGs that contain two or three arachidonic acids. In four TAGs containing PUFA, i.e. EEE, EEA, EAA and AAA, N-starvation caused a rapid fivefold increase in ARA content and the ratio of TAGs containing ARA, i.e. AEE to AAA increased tenfold relative to control. Regioisomeric characterization of triacylglycerols containing palmitic, arachidonic (ARA) and eicosapentaenoic acids (EPA) showed that

  黄绿藻 Trachydiscus minutus (Eustigmatophyceae, Heterocontophyta) 在标准培养基和氮磷饥饿条件下培养，并通过 RP-HPLC/MS-APCI 分析其三酰甘油。三酰甘油的分子种类包括总共74种具有至少一种多不饱和脂肪酸的三酰甘油。首次在黄绿色藻类中鉴定出多不饱和甘油三酯。N 饥饿使含有 EPA 的 TAG 减少了近 50%，同时也减少了含有 ARA 的 TAG，而 P 饥饿对那些含有两种或三种花生四烯酸的 TAG 产生了相当大的影响。在含有 PUFA 的四种 TAG，即 EEE、EEA、EAA 和 AAA 中，N 饥饿导致 ARA 含量和含有 ARA 的 TAG 比例迅速增加了五倍，即 AEE 到 AAA 相对于对照增加了十倍。含有棕榈酸、花生四烯酸 (ARA) 和二十碳五烯酸 (EPA) 的三酰基甘油的区域异构特征表明，位置异构体的比例受
• 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.