1,3-dicapryloyl-2-oleyl-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: 1,3-dicapryloyl-2-oleyl-glycerol
• 英文别名: 1,3-capryloyl-2-oleoyl-glycerol；1,3-Di(octanoyloxy)propan-2-yl (Z)-octadec-9-enoate
• 化学式: C₃₇H₆₈O₆
• 分子量: 608.943
• InChiKey: AQMIKCLTKVMFHY-ZCXUNETKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.4
• 重原子数：
  43
• 可旋转键数：
  35
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 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：

  辛酸乙烯酯 在 molecular sieve 、 immobilized lipases from Burkholderia cepacia 、 lipase B from Candida antarctica 作用下， 以 正己烷 为溶剂， 反应 3.0h， 生成 1,3-dicapryloyl-2-oleyl-glycerol
  参考文献：
  名称：

  脂肪酶催化的1,3-二酰甘油酯合成结构化三酰甘油酯

  摘要：

  AbstractA new method for the lipase‐catalyzed synthesis of structured TAG (ST) is described. First, sn1,3‐dilaurin or‐dicaprylin were enzymatically synthesized using different published methods. Next, these were esterified at the sn2‐position with oleic acid or its vinyl ester using different lipases. Key to successful enzymatic synthesis of ST was the choice of a lipase with appropriate FA specificity, i.e., one that does not act on the FA already present in the sn1,3‐DAG, but that at the same time exhibits high selectivity and activity toward the FA to be introduced. Reactions were performed in the presence of organic solvents or in solvent‐free systems under reduced pressure. With this strategy, mixed ST containing the desired compounds 1,3‐dicaprylol‐2‐oleyl‐glycerol or 1,3‐dilauroyl‐2‐oleyl‐glycerol (CyOCy or LaOLa) were obtained at 87 and 78 mol% yield, respectively, using immobilized lipases from Burkholderia cepacia (Amano PS‐D) in n‐hexane at 60°C. However, regiospecific analysis with porcine pancreatic lipase indicated that in CyOCy, 25.7% caprylic acid and in LaOLa 11.1% lauric acid were located at the sn2‐position. Oleic acid vinyl ester was a better acyl donor than oleic acid. Esterification of sn1,3‐DAG and free oleic acid gave very low yield (<20%) of ST in a solvent system and moderate yield (>50%) in a solvent‐free system under reduced pressure.

  DOI：

  10.1007/s11746-004-0873-z

文献信息

• Two-step enzymatic reaction for the synthesis of pure structured triacylglycerides
  作者：Mohamed M. Soumanou、Uwe T. Bornscheuer、Rolf D. Schmid

  DOI：10.1007/s11746-998-0209-2

  日期：1998.6

  AbstractStructured triacylglycerides with medium‐chain fatty acids (caprylic acid) in sn1‐ and sn3‐positions and a long‐chain unsaturated fatty acid (oleic or linoleic acid) in the sn2‐position of glycerol (MLM) were synthesized by lipase catalysis in a two‐step process. First, pure 2‐monoacylglycerides (2‐MG) were synthesized by alcoholysis of triacylglycerides (triolein, trilinolein, or peanut oil) in organic solvents with 1,3‐regiospecific lipases (from Rhizomucor miehei, Rhizopus delemar, and Rhizopus javanicus). The 2‐MG were purified by crystallization and obtained in up to 71.8% yield. These 2‐MG were esterified in a second reaction with caprylic acid in n‐hexane to form almost pure MLM. For 2‐MG obtained from peanut oil, the final product contained more than 90% caprylic acid in the sn1‐ and sn3‐positions, whereas the sn2‐position was composed of 98.5% unsaturated long‐chain fatty acids. Reaction conditions for both steps were optimized with respect to source and immobilization of lipase, water activity, and solvent.
• EMULSION AND USE OF THE EMULSION AS A PARENTERAL PREPARATION
  申请人：NOVO NORDISK A/S

  公开号：EP0437521A1

  公开（公告）日：1991-07-24
• [EN] EMULSION AND USE OF THE EMULSION AS A PARENTERAL PREPARATION
  申请人：NOVO NORDISK A/S

  公开号：WO1990003787A1

  公开（公告）日：1990-04-19

  (EN) The emulsion has an aqueous, continuous phase and containing as the discontinuous phase the triglycerides 2-oleyl-1,3-di(octanoyl/decanoyl) glycerol, formulated for parenteral use. This emulsion exhibits a better bioavailability than hitherto known parenteral emulsions used as a source for oleic acid.(FR) L'émulsion comporte une phase aqueuse continue et contient à titre de phase discontinue les triglycérides 2-oleyl-1,3-di(octanoyl/décanoyl), formulés pour une utilisation parentérale. Cette émulsion présente une meilleure biodisponibilité que les émulsions parentérales connues à ce jour qui sont utilisées comme source d'acide oléique.
• Lipase-catalyzed synthesis of structured triacylglycerides from 1,3-diacylglycerides
  作者：Sirirung Wongsakul、Aran H-Kittikun、Uwe T. Bornscheuer

  DOI：10.1007/s11746-004-0873-z

  日期：2004.2

  AbstractA new method for the lipase‐catalyzed synthesis of structured TAG (ST) is described. First, sn1,3‐dilaurin or‐dicaprylin were enzymatically synthesized using different published methods. Next, these were esterified at the sn2‐position with oleic acid or its vinyl ester using different lipases. Key to successful enzymatic synthesis of ST was the choice of a lipase with appropriate FA specificity, i.e., one that does not act on the FA already present in the sn1,3‐DAG, but that at the same time exhibits high selectivity and activity toward the FA to be introduced. Reactions were performed in the presence of organic solvents or in solvent‐free systems under reduced pressure. With this strategy, mixed ST containing the desired compounds 1,3‐dicaprylol‐2‐oleyl‐glycerol or 1,3‐dilauroyl‐2‐oleyl‐glycerol (CyOCy or LaOLa) were obtained at 87 and 78 mol% yield, respectively, using immobilized lipases from Burkholderia cepacia (Amano PS‐D) in n‐hexane at 60°C. However, regiospecific analysis with porcine pancreatic lipase indicated that in CyOCy, 25.7% caprylic acid and in LaOLa 11.1% lauric acid were located at the sn2‐position. Oleic acid vinyl ester was a better acyl donor than oleic acid. Esterification of sn1,3‐DAG and free oleic acid gave very low yield (<20%) of ST in a solvent system and moderate yield (>50%) in a solvent‐free system under reduced pressure.