1,3-dilauroyl-2-oleyl-glycerol | 51067-90-4

• 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-dilauroyl-2-oleyl-glycerol
• 英文别名: 1,3-bis-lauroyloxy-2-oleoyloxy-propane；1,3-Bis-lauroyloxy-2-oleoyloxy-propan；1,3-Dilauroyl-2-oleoylglycerol；1,3-di(dodecanoyloxy)propan-2-yl (Z)-octadec-9-enoate
• CAS: 51067-90-4
• 化学式: C₄₅H₈₄O₆
• 分子量: 721.158
• InChiKey: FLJRTILNGCDXTF-DQRAZIAOSA-N

物化性质

• 沸点：
  708.6±30.0 °C(Predicted)
• 密度：
  0.929±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  17.8
• 重原子数：
  51
• 可旋转键数：
  43
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  月桂酸乙烯酯 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 8.0h， 生成 1,3-dilauroyl-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

• Unsaturated Synthetic Glycerides. V. Unsymmetrical Monoelaidyl-Disaturated and Monosaturated-Dielaidyl Triglycerides¹
  作者：B. F. Daubert

  DOI：10.1021/ja01230a041

  日期：1944.2
• METHOD OF PRODUCING HARD BUTTER
  申请人：The Nisshin OilliO Group, Ltd.

  公开号：EP2204097B1

  公开（公告）日：2016-03-09
• PROCESS FOR PREPARING HARD BUTTER
  申请人：Arimoto Shin

  公开号：US20100255152A1

  公开（公告）日：2010-10-07

  The present invention relates to a process for preparing a hard butter, which comprises conducting transesterification between one or more selected from the group consisting of straight-chain saturated C16-22 fatty acids and lower alcohol esters thereof and a triglyceride having oleoyl group and/or linoleoyl group at the 2-position with an action of a granulated powder lipase comprising a lipase derived from Rhizopus oryzae and/or Rhizopus delemar and a soybean powder, and removing the granulated powder lipase after the transesterification. The process is industrially suitable process for preparing a hard butter, which have excellent properties as a cacao butter equivalent.
• US8980346B2
  申请人：——

  公开号：US8980346B2

  公开（公告）日：2015-03-17
• 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.