(9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid trans-(2-phenyl-[1,3]dioxolan-4-yl)methyl ester

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid trans-(2-phenyl-[1,3]dioxolan-4-yl)methyl ester
• 英文别名: [(2R,4S)-2-phenyl-1,3-dioxolan-4-yl]methyl (9Z,12Z,15Z)-octadeca-9,12,15-trienoate
• 化学式: C₂₈H₄₀O₄
• 分子量: 440.623
• InChiKey: BOYWFEHAUNZTHN-BTPXYZHASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  32
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  十七烷酸 、 (9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid trans-(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63%的产率得到octadeca-9,12,15-trienoic acid 2,3-bis(heptadecanoyloxy)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
• 作为产物：
  描述：

  Γ-十八碳三烯酸 、 苯甲醛 、 甘油 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以363 mg的产率得到(9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid cis-2-phenyl-[1,3]dioxan-5-yl 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.