2,3-bis[[(E)-octadec-9-enoyl]oxy]propyl (Z)-octadec-9-enoate

• 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: 2,3-bis[[(E)-octadec-9-enoyl]oxy]propyl (Z)-octadec-9-enoate
• 化学式: C₅₇H₁₀₄O₆
• 分子量: 885.449
• InChiKey: PHYFQTYBJUILEZ-UCTUUELPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  22.4
• 重原子数：
  63
• 可旋转键数：
  53
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.84
• 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：

  反油酸 、 1-monooleoyl glycerol 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 四氯化碳 为溶剂， 反应 2.0h， 以87%的产率得到2,3-bis[[(E)-octadec-9-enoyl]oxy]propyl (Z)-octadec-9-enoate
  参考文献：
  名称：

  EOE和EEO，含有松香油酸和脂肪酸油的三酰基甘油的合成和物理性质

  摘要：

  AbstractSymmetrical and non‐symmetrical triacylglycerols (TAG) containing oleic (O; 9c‐18:1) and elaidic (E; 9t‐18:1) acids were required as part of a study relating the physical characteristics and functionality of trans‐containing TAG with the mouth feel, taste characteristics and related characteristics desired by consumers in frying oils and pastries. To replace the trans isomers in frying oils—a significant part of frying oils prepared by partial hydrogenation of vegetable oils—without loss of the sensory properties desired by consumers, required the initiation of a study relating the structure of trans‐containing TAG with such characteristics as melting range, drop points, and other crystalline properties. Elaidic acid was esterified to trielaidin (EEE), and the EEE partially converted (glycerol/p‐toluenesulfonic acid) to a mixture containing ca. 40% DAG (the 1,3‐ and 1,2‐isomers). The DAG fraction was separated by silica gel chromatography, the 1,3‐dielaidylglycerol (1,3EE‐DAG) isomer isolated (structural purity >99%) by crystallization from acetone and esterified with oleic acid (O) to yield EOE. The 1(3)O‐MAG was purchased commercially and esterified with E acid to prepare OEE. Both syntheses yielded multi‐gram quantities of EOE and EEO, in 80–85% yields, and with structural purities >99%. Thus, by careful selection of the thermodynamically more‐stable MAG or DAG precursors, the symmetrical EOE and non‐symmetrical EEO isomers could be readily synthesized, and their drop point and melting point values determined.

  DOI：

  10.1007/s11746-007-1056-2