1,2-distearoyl-3-oleoylglycerol | 39202-22-7

• 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-distearoyl-3-oleoylglycerol
• 英文别名: 3-Oleoyl-1,2-distearoyl-sn-glycerol；1,2-dioctadecanoyl-3-(9Z-octadecenoyl)-sn-glycerol；[(2R)-2-octadecanoyloxy-3-[(Z)-octadec-9-enoyl]oxypropyl] octadecanoate
• CAS: 39202-22-7
• 化学式: C₅₇H₁₀₈O₆
• 分子量: 889.481
• InChiKey: YFFIQXNTTVSKJC-NZEOUKRFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  24.3
• 重原子数：
  63
• 可旋转键数：
  55
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 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：

  (+-)-1-oleoyloxy-2,3-bis-stearoyloxy-propane 以 甲醇 、 正己烷 、 异丙醇 为溶剂， 生成 1,2-distearoyl-3-oleoylglycerol 、 2,3-dioctadecanoyl-1-cis-octadec-9-enoyl-sn-glycerol
  参考文献：
  名称：

  Enantioselective chromatography in analysis of triacylglycerols common in edible fats and oils

  摘要：

  Enantiomers of racemic triacylglycerol (TAG) mixtures were separated using two chiral HPLC columns with a sample recycling system and a UV detector. A closed system without sample derivatisation enabled separation and identification by using enantiopure reference compounds of eleven racemic TAGs with C12-C22 fatty acids with 0-2 double bonds. The prolonged separation time was compensated for by fewer pretreatment steps. Presence of one saturated and one unsaturated fatty acid in the asymmetric TAG favoured the separation. Enantiomeric resolution, at the same time with stronger retention of TAGs, increased with increasing fatty acid chain length in the sn-1(3) position. Triunsaturated TAGs containing oleic, linoleic or palmitoleic acids did not separate. The elution order of enantiomers was determined by chemoenzymatically synthesised enantiopure TAGs with a co-injection method. The method is applicable to many natural fats and oils of low unsaturation level assisting advanced investigation of lipid synthesis and metabolism. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.foodchem.2014.09.135

文献信息

• Enantioselective chromatography in analysis of triacylglycerols common in edible fats and oils
  作者：Marika Kalpio、Matts Nylund、Kaisa M. Linderborg、Baoru Yang、Björn Kristinsson、Gudmundur G. Haraldsson、Heikki Kallio

  DOI：10.1016/j.foodchem.2014.09.135

  日期：2015.4

  Enantiomers of racemic triacylglycerol (TAG) mixtures were separated using two chiral HPLC columns with a sample recycling system and a UV detector. A closed system without sample derivatisation enabled separation and identification by using enantiopure reference compounds of eleven racemic TAGs with C12-C22 fatty acids with 0-2 double bonds. The prolonged separation time was compensated for by fewer pretreatment steps. Presence of one saturated and one unsaturated fatty acid in the asymmetric TAG favoured the separation. Enantiomeric resolution, at the same time with stronger retention of TAGs, increased with increasing fatty acid chain length in the sn-1(3) position. Triunsaturated TAGs containing oleic, linoleic or palmitoleic acids did not separate. The elution order of enantiomers was determined by chemoenzymatically synthesised enantiopure TAGs with a co-injection method. The method is applicable to many natural fats and oils of low unsaturation level assisting advanced investigation of lipid synthesis and metabolism. (C) 2014 Elsevier Ltd. All rights reserved.