(9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid trans-2-phenyl-[1,3]dioxan-5-yl ester | 1258782-47-6

• 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]dioxan-5-yl ester
• CAS: 1258782-47-6
• 化学式: C₂₈H₄₀O₄
• 分子量: 440.623
• InChiKey: IRBHZQLYNSNFLQ-NBOIUMCYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.23
• 重原子数：
  32.0
• 可旋转键数：
  15.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  油酸 、 (9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid trans-2-phenyl-[1,3]dioxan-5-yl ester 在 三氟乙酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以38%的产率得到2-α-Linolenoyloxy-1,3-bis-oleoyloxy-propan
  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 、 2-苯基-1,3-二氧六环-5-醇 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 48.0h， 以39%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