1,2-dipalmitoyl-3-elaidoyl-rac-glycerol | 93452-43-8

• 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-dipalmitoyl-3-elaidoyl-rac-glycerol
• 英文别名: 1,2-Dipalmito-3-elaidin；2,3-di(hexadecanoyloxy)propyl (E)-octadec-9-enoate
• CAS: 93452-43-8
• 化学式: C₅₃H₁₀₀O₆
• 分子量: 833.373
• InChiKey: YHMDGPZOSGBQRH-OCEACIFDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  22.1
• 重原子数：
  59
• 可旋转键数：
  51
• 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：

  反油酸 、 alkaline earth salt of/the/ methylsulfuric acid 在 吡啶 、 硼酸 、 对甲苯磺酸 作用下， 以 氯仿 为溶剂， 反应 6.67h， 生成 1,2-dipalmitoyl-3-elaidoyl-rac-glycerol
  参考文献：
  名称：

  含有桉树酸的混合二酸甘油三酸酯的合成及理化特性

  摘要：

  AbstractThe synthesis of symmetrical and asymmetrical palmito‐ and stearo‐elaidic triglycerides (PEP, SES, EPP, PEE, ESS, and SEE, in which P=palmitic, S=stearic, and E=elaidic acid) was undertaken to investigate their polymorphism. The chemical pathways and the purification steps, including crystallization and adsorption chromatography, are described. The different chromatographic analyses (gas‐liquid chromatography: carbon number profile and fatty acid methyl ester profile, and high‐performance liquid chromatography) revealed that the purity of the synthesized products was superior to 99% except for SES (>96%). The thermal behavior, as well as the polymorphism of these triglycerides, has been investigated by means of differential scanning calorimetry and powder X‐ray diffraction spectroscopy at variable temperatures. The six compounds crystallize according to a double chainlength packing. The most stable polymorphic form of palmito‐elaidic triglycerides belongs to the β′ variety, whereas the stearo‐elaidic triglycerides are β stable.

  DOI：

  10.1007/s11746-998-0043-6

文献信息

• Synthesis and Physical Properties of Symmetrical and Non‐symmetrical Triacylglycerols Containing Two Palmitic Fatty Acids
  作者：R. O. Adlof、G. R. List

  DOI：10.1007/s11746-007-1173-y

  日期：2008.2

  AbstractA series of symmetrical (ABA) and non‐symmetrical (AAB) triacylglycerol (TAG) isomers containing “A,” palmitic (P; 16:0) acid, and “B,” either oleic (O; 9c‐18:1), elaidic (E; 9t‐18:1), linoleic (L; 9c,12c‐18:2) or linolenic (Ln; 9c,12c,15c‐18:3) fatty acids were synthesized by esterification of the thermodynamically more‐stable 1,3‐di‐ or 1(3)‐monoacylglycerols [1,3‐DAG or 1(3)‐MAG], respectively. 1,3‐dipalmitoylglycerol (1,3P‐DAG) was esterified with O, L or Ln acid to prepare the symmetrical TAG isomers POP, PLP and PLnP, while the O‐ E‐, L‐ and Ln‐1(3)MAG precursors, synthesized or obtained commercially, were esterified with P acid to prepare the non‐symmetrical TAG isomers OPP, EPP, LPP and LnPP, respectively. The drop point(s), solid fat content and melting point values of the synthesized TAG were determined. The 1,3‐dipalmitoylglycerol (1,3P‐DAG) and 1(3)P‐MAG precursors were prepared, in multi‐gram quantities, by partial glycerolysis (glycerol/p‐toluenesulfonic acid) of tripalmitin. After fractionation by silica gel chromatography, the 1(3)P‐MAG and 1,3P‐DAG isomers (ca. 80% of total MAG or DAG) were purified (>98%) by crystallization from acetone [silver ion‐HPLC was utilized to determine the structural purities of the DAG (or MAG) precursors, and the synthesized TAG]. Esterification of the appropriate, thermodynamically more‐stable MAG or DAG precursors was found to be a very versatile method for synthesis (in 80–90% yields) of multi‐gram (3–5 g) quantities of symmetrical and non‐symmetrical TAG isomers, in chemical and structural purities of >96 and 97–99%, respectively.
• COCKMAN, SAMANTHA J.;JOLL, CYNTHIA A.;MORTIMER, BOK-CHENG;REDGRAVE, TREVO+, AUSTRAL. J. CHEM., 43,(1990) N2, C. 2093-2097
  作者：COCKMAN, SAMANTHA J.、JOLL, CYNTHIA A.、MORTIMER, BOK-CHENG、REDGRAVE, TREVO+

  DOI：——

  日期：——
• Synthesis and physicochemical characterization of mixed diacid triglycerides that contain elaidic acid
  作者：P. Elisabettini、G. Lognay、A. Desmedt、C. Culot、N. Istasse、E. Deffense、F. Durant

  DOI：10.1007/s11746-998-0043-6

  日期：1998.2

  AbstractThe synthesis of symmetrical and asymmetrical palmito‐ and stearo‐elaidic triglycerides (PEP, SES, EPP, PEE, ESS, and SEE, in which P=palmitic, S=stearic, and E=elaidic acid) was undertaken to investigate their polymorphism. The chemical pathways and the purification steps, including crystallization and adsorption chromatography, are described. The different chromatographic analyses (gas‐liquid chromatography: carbon number profile and fatty acid methyl ester profile, and high‐performance liquid chromatography) revealed that the purity of the synthesized products was superior to 99% except for SES (>96%). The thermal behavior, as well as the polymorphism of these triglycerides, has been investigated by means of differential scanning calorimetry and powder X‐ray diffraction spectroscopy at variable temperatures. The six compounds crystallize according to a double chainlength packing. The most stable polymorphic form of palmito‐elaidic triglycerides belongs to the β′ variety, whereas the stearo‐elaidic triglycerides are β stable.