1,2-dioleoyl-3-stearoylglycerol | 79517-06-9

• 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-dioleoyl-3-stearoylglycerol
• 英文别名: Stearooleoelaidin；Stearoelaido-olein；1,2-Dioleoyl-3-stearoyl-sn-glycerol；[(2S)-2,3-bis[[(Z)-octadec-9-enoyl]oxy]propyl] octadecanoate
• CAS: 79517-06-9
• 化学式: C₅₇H₁₀₆O₆
• 分子量: 887.465
• InChiKey: RYNHWWNZNIGDAQ-WNMJAFDRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  23.3
• 重原子数：
  63
• 可旋转键数：
  54
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  油酸酐 在 六甲基磷酰三胺 、 lithium bromide 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 1,2-dioleoyl-3-stearoylglycerol
  参考文献：
  名称：

  Stereospecific synthesis of selected triglycerides: comments on acyl migration and analysis of configuration

  摘要：

  Symmetrical and stereospecifically defined triglycerides have been prepared from racemic and (R)- and (S)-glycidol, respectively. The synthetic sequence allows the incorporation of sensitive fatty acids such as linolenic acid. Justification for retention of configuration and absence of acyl migrations during the synthesis is provided by the H-1-NMR spectra of triglycerides that are replaced at the sn-1 and sn-3 positions with enantiomers of alpha-methoxytrifluoromethylphenylacetic acid (bis-MTPA esters). Partial hydrolysis of synthetic symmetrical triglycerides catalyzed by the lipase of Rhizopus oryzae was used to demonstrate the homogeneity of these preparations.

  DOI：

  10.1016/0009-3084(94)90101-5

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.
• Kawasaki T.; Snyder F., J Biol Chem, 1988, 0021-9258, 2593-6
  作者：Kawasaki T.、Snyder F.

  DOI：——

  日期：——
• Saccharomyces cerevisiae phospholipid:diacylglycerol acyl transferase (PDAT) devoid of its membrane anchor region is a soluble and active enzyme retaining its substrate specificities
  作者：Alokesh Ghosal、Antoni Banas、Ulf Ståhl、Anders Dahlqvist、Ylva Lindqvist、Sten Stymne

  DOI：10.1016/j.bbalip.2007.10.007

  日期：2007.12

  A N-terminal deleted version of the Saccharomyces cerevisiae phospholipid:diacylglycerol acyltransferase (ScPDAT), lacking the predicted membrane-spanning region, was fused in frame with alpha-factor secretion signal and expressed in Pichia pastoris under the control of the methanol inducible alcohol oxidase promoter. This resulted in a truncated, soluble and highly active PDAT protein secreted into the culture medium of the recombinant cells. The soluble as well as native membrane bound enzymes was shown to be glycosylated and extensive deglycosylation severely lowered the activity. The production of a soluble and extracellular PDAT allowed us to investigate substrate preferences of the enzyme without interference of endogenous lipids and enzymes. Similar to the membrane bound counterpart, the highest activity was achieved with acyl groups at sn-2 position of phosphatidylethanolamine as acyl donor and 1,2-diacylglycerols as acyl acceptor. The soluble enzyme was also able to catalyze, at a low rate, a number of transacylation reactions between various neutral lipids and between polar lipids and neutral lipids others than diacylglycerols, including acylation of long chain alcohols. (c) 2007 Elsevier B.V. All rights reserved.
• Stereospecific synthesis of selected triglycerides: comments on acyl migration and analysis of configuration
  作者：Philip E. Sonnet、Robert L. Dudley

  DOI：10.1016/0009-3084(94)90101-5

  日期：1994.8

  Symmetrical and stereospecifically defined triglycerides have been prepared from racemic and (R)- and (S)-glycidol, respectively. The synthetic sequence allows the incorporation of sensitive fatty acids such as linolenic acid. Justification for retention of configuration and absence of acyl migrations during the synthesis is provided by the H-1-NMR spectra of triglycerides that are replaced at the sn-1 and sn-3 positions with enantiomers of alpha-methoxytrifluoromethylphenylacetic acid (bis-MTPA esters). Partial hydrolysis of synthetic symmetrical triglycerides catalyzed by the lipase of Rhizopus oryzae was used to demonstrate the homogeneity of these preparations.