1,3-distearoylglycero-2-phosphocholine | 58489-65-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油磷脂
• 英文名称: 1,3-distearoylglycero-2-phosphocholine
• 英文别名: 1,3-Distearoylglycero-3-phosphocholin；Distearo-β-lecithin；{2-[(β,β'-bis-stearoyloxy-isopropoxy)-hydroxy-phosphoryloxy]-ethyl}-trimethyl-ammonium betaine；Stearo-β-lecithin；{2-[(β,β'-Bis-stearoyloxy-isopropoxy)-hydroxy-phosphoryloxy]-aethyl}-trimethyl-ammonium-betain；beta-Lecithin；1,3-di(octadecanoyloxy)propan-2-yl 2-(trimethylazaniumyl)ethyl phosphate
• CAS: 58489-65-9
• 化学式: C₄₄H₈₈NO₈P
• 分子量: 790.158
• InChiKey: QVOSSHZMHWUKKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.6
• 重原子数：
  54
• 可旋转键数：
  44
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  111
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  1,3-二硬脂酸甘油酯 在 吡啶 作用下， 以 乙醚 、 氯仿 、 异丙醇 、 乙腈 为溶剂， 反应 1.0h， 生成 1,3-distearoylglycero-2-phosphocholine
  参考文献：
  名称：

  1,3-Diacylglycero-2-phosphocholines — synthesis, aggregation behaviour and properties as inhibitors of phospholipase D

  摘要：

  A series of 1,3-diacylglycero-2-phosphocholines (1,3-PCs) with acyl chain lengths of C-8-C-18 were synthesised by chemical introduction of the phosphocholine moiety into the regioisomerically pure 1,3-diacylglycerols, which were obtained from glycerol and the vinyl esters of fatty acid by means of lipase from Rhizomucor mihei. The I,3-PCs being regioisomers of the natural glycerophospholipids were studied with respect to their aggregation behaviour in the absence and in the presence of sodium dodecylsulfate (SDS) as well as their properties as substrates and inhibitors of phospholipase D (PLD) from cabbage. While the main structures of the pure 1,3-PCs were micelles (C-8), liposomes (C-10, C-12) or planar bilayers (C-14, C-16, C-18), the addition of SDS resulted in the formation of mixed micelles (C-8, C-10) and mixed liposomes (C-12, C-14, C-16, C-18). None of the 1,3-PCs was found to be hydrolysed by PLD, whereas all of them showed inhibitory properties in the standard assay for PLD. The inhibitory power was strongest with 1,3-didecanoylglycero-2-phosphocholine (IC50 = 43 mu M). (C) Elsevier Science Ireland Ltd. All rights reserved.

  DOI：

  10.1016/s0009-3084(99)00120-6

文献信息

• Synthesen von Cholinphosphatiden, I. Zur Synthese von α- und β-Lecithinen und ihren Ätheranaloga
  作者：Hansjörg Eibl、Dieter Arnold、Hans Ulrich Weltzien、Otto Westphal

  DOI：10.1002/jlac.19677090124

  日期：1967.12.18

  Das Verfahren zur Synthese von Lecithinen und ihren Ätheranalogen, bei welchem Diacyl-bzw. Di-O-alkyl-diglyceride (1) mit β-Bromäthyl-phosphorsäuredichlorid bei Gegenwart von Triäthylamin umgesetzt werden und anschließend mit Trimethylamin ins Phosphorylcholin 4 übergeführt werden, wurde so abgewandelt, daß beliebige, auch kürzerkettige (bis C8), Lecithine und ihre Ätheranaloga analysenrein und dü

  卵磷脂及其醚类似物的合成方法，其中二酰基或。在三乙胺存在下，使二-O-烷基甘油二酸酯（1）与β-溴乙基-磷酸二氯化物反应，然后用三甲胺将其转化为磷酰胆碱4，以使任何短链（最高为C 8）改性，卵磷脂及其醚类似物可通过薄层色谱法以分析纯的形式均匀地获得（参见表1）。
• Gruen; Limpaecher, Chemische Berichte, 1927, vol. 60, p. 147,156
  作者：Gruen、Limpaecher

  DOI：——

  日期：——