1,2-diarachidonoyl-3-palmitoyl-rac-glycerol

• 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-diarachidonoyl-3-palmitoyl-rac-glycerol
• 英文别名: [3-hexadecanoyloxy-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyl]oxypropyl] (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate
• 化学式: C₅₉H₉₈O₆
• 分子量: 903.424
• InChiKey: UBGUHMDKBGQUND-URCGVKMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  20.3
• 重原子数：
  65
• 可旋转键数：
  50
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.68
• 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：

  甘油棕榈酸酯 、 花生四烯酸 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 50.0h， 以54%的产率得到1,2-diarachidonoyl-3-palmitoyl-rac-glycerol
  参考文献：
  名称：

  Chemical synthesis and NMR characterization of structured polyunsaturated triacylglycerols

  摘要：

  The chemical synthesis of pure triacylglycerol (TAG) regioisomers, that contain long chain polyunsaturated fatty acids, such as arachidonic acid (AA) or docosahexaenoic acid (DHA), and saturated fatty acids, Such as lauric acid (La) or palmitic acid (P), at defined positions, is described. A single step methodology using (benzotriazol-1-yloxy)-tripyrrolidinophosphonium hexafluorophosphate (PyBOP), an activator of carboxyl group commonly used in peptide synthesis and occasionally used in carboxylic acid esterification, has been developed for structured TAG synthesis. Identification of the fatty acyl chains for each TAG species was confirmed by atmospheric pressure chemical ionisation mass spectrometry (APCI-MS) and fatty acid positional distribution was determined by H-1 and C-13 NMR spectra. The generic described procedures can be applied to a large variety Of Substrates and was used for the production of specific triacylglycerols of defined molecular structures, with high regioisomeric purity. Combination of MS and NMR was shown to be an efficient tool for structural analysis of TAG. In particular. some NMR signals were demonstrated to be regioisomer specific, allowing rapid positional analysis of LC-PUFA containing TAG. (C) 2005 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2005.11.004

文献信息

• Chemical synthesis and NMR characterization of structured polyunsaturated triacylglycerols
  作者：Laëtitia Fauconnot、Fabien Robert、Renaud Villard、Fabiola Dionisi

  DOI：10.1016/j.chemphyslip.2005.11.004

  日期：2006.2

  The chemical synthesis of pure triacylglycerol (TAG) regioisomers, that contain long chain polyunsaturated fatty acids, such as arachidonic acid (AA) or docosahexaenoic acid (DHA), and saturated fatty acids, Such as lauric acid (La) or palmitic acid (P), at defined positions, is described. A single step methodology using (benzotriazol-1-yloxy)-tripyrrolidinophosphonium hexafluorophosphate (PyBOP), an activator of carboxyl group commonly used in peptide synthesis and occasionally used in carboxylic acid esterification, has been developed for structured TAG synthesis. Identification of the fatty acyl chains for each TAG species was confirmed by atmospheric pressure chemical ionisation mass spectrometry (APCI-MS) and fatty acid positional distribution was determined by H-1 and C-13 NMR spectra. The generic described procedures can be applied to a large variety Of Substrates and was used for the production of specific triacylglycerols of defined molecular structures, with high regioisomeric purity. Combination of MS and NMR was shown to be an efficient tool for structural analysis of TAG. In particular. some NMR signals were demonstrated to be regioisomer specific, allowing rapid positional analysis of LC-PUFA containing TAG. (C) 2005 Elsevier Ireland Ltd. All rights reserved.