1,2-dieicosapentaenoyl-3-palmitoylglycerol

• 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-dieicosapentaenoyl-3-palmitoylglycerol
• 英文别名: (5'Z,8'Z,11'Z,14'Z,17'Z)-5Z,8Z,11Z,14Z,17Z-eicosapentaenoic acid, 1,1'-[1-[[(1-oxohexadecyl)oxy]methyl]-1,2-ethanediyl] ester；[3-hexadecanoyloxy-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: C₅₉H₉₄O₆
• 分子量: 899.392
• InChiKey: QTNYDZPWHCXVJM-HTSKAZOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  18.9
• 重原子数：
  65
• 可旋转键数：
  48
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.61
• 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：

  全顺式二十碳五烯酸 、 甘油棕榈酸酯 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58%的产率得到1,2-dieicosapentaenoyl-3-palmitoylglycerol
  参考文献：
  名称：

  氮和磷饥饿对海藻 Trachydiscus minutus 中多不饱和甘油三酯组成的影响，包括位置异构体分布

  摘要：

  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

  DOI：

  10.1016/j.phytochem.2011.08.017

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.
• 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