(Z,Z,Z,Z,Z,Z)-docosa-4,7,10,13,16,19-hexaenoic acid 2,3-bis((Z)-octadec-9-enoyloxy)propyl ester | 116198-39-1

• 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,Z)-docosa-4,7,10,13,16,19-hexaenoic acid 2,3-bis((Z)-octadec-9-enoyloxy)propyl ester
• 英文别名: 4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoic acid, 2,3-bis[[(9Z)-1-oxo-9-octadecen-1-yl]oxy]propyl ester；2,3-bis[[(Z)-octadec-9-enoyl]oxy]propyl (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoate
• CAS: 116198-39-1
• 化学式: C₆₁H₁₀₂O₆
• 分子量: 931.477
• InChiKey: QFVBKJOYLFHVKV-DNVUEQEESA-N

物化性质

• 沸点：
  849.0±65.0 °C(Predicted)
• 密度：
  0.935±0.06 g/cm3(Predicted)
• 溶解度：
  氯仿：微溶； DMF：10 mg/ml；乙醇：10 mg/ml；乙醇:PBS(pH 7.2) (1:1): 0.5 mg/ml

计算性质

• 辛醇/水分配系数(LogP)：
  18.54
• 重原子数：
  67.0
• 可旋转键数：
  49.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  78.9
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  油酸 、 (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoic acid (2-phenyl-[1,3]dioxolan-4-yl)methyl ester 在 三氟乙酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以60%的产率得到(Z,Z,Z,Z,Z,Z)-docosa-4,7,10,13,16,19-hexaenoic acid 2,3-bis((Z)-octadec-9-enoyloxy)propyl ester
  参考文献：
  名称：

  Rapid access to structured triacylglycerols acylated with n-3 polyunsaturated fatty acids for nutritional applications

  摘要：

  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.

  DOI：

  10.1016/j.tet.2010.09.070

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.