(Z,Z,Z,Z,Z)-icosa-5,8,11,14,17-pentaenoic acid 2-((Z)-octadec-9-enoyloxy)-1-((Z)-octadec-9-enoyloxymethyl)ethyl ester

• 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: (Z,Z,Z,Z,Z)-icosa-5,8,11,14,17-pentaenoic acid 2-((Z)-octadec-9-enoyloxy)-1-((Z)-octadec-9-enoyloxymethyl)ethyl ester
• 英文别名: 1,3-dioleoyl-2-5,8,11,14,17-eicosapentanoyl glyceride；1-Oleoyl-2-eicosapentaenoyl-3-oleoyl-glycerol；1,3-bis[[(Z)-octadec-9-enoyl]oxy]propan-2-yl (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoate
• 化学式: C₅₉H₁₀₀O₆
• 分子量: 905.439
• InChiKey: KYXSSOQPQVYSGO-SCHGNYNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  20.7
• 重原子数：
  65
• 可旋转键数：
  51
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 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 、 二油精 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 生成 (Z,Z,Z,Z,Z)-icosa-5,8,11,14,17-pentaenoic acid 2-((Z)-octadec-9-enoyloxy)-1-((Z)-octadec-9-enoyloxymethyl)ethyl ester
  参考文献：
  名称：

  含二十碳五烯酸的三酰基甘油的合成异构体的自氧化

  摘要：

  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.

  DOI：

  10.1007/s11746-997-0178-x

文献信息

• Rapid access to structured triacylglycerols acylated with n-3 polyunsaturated fatty acids for nutritional applications
  作者：Emilie Vaique、Alexandre Guy、Leslie Couedelo、Isabelle Gosse、Thierry Durand、Maud Cansell、Sandra Pinet

  DOI：10.1016/j.tet.2010.09.070

  日期：2010.11

  In order to better understand the metabolic fate of n-3 polyunsaturated fatty acids (PUFAs), an efficient access to symmetrical and unsymmetrical triacylglycerols (TGs), esterified with PUFAs, with known high purity, is required. In this context, we optimized the esterification of a mixture of glycerols protected as dioxane and dioxolane with PUFAs. The kinetics of this reaction depends on various factors, such as the fatty acid chain length and the stereochemistry of the dioxane. Then, one-pot acetal hydrolysis and esterification of hydroxyl groups led to the desired structured TGs without either double bond isomerization or acyl migration (except when symmetrical TGs are acylated with long-chain saturated fatty acids in external positions). PUFAs location on the glycerol backbone was assayed by NMR, HPLC and pancreatic lipase hydrolysis. (C) 2010 Elsevier Ltd. All rights reserved.
• 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.