2,3-di-O-n-dodecanoyl-sn-glycerol | 61475-84-1

• 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-di-O-n-dodecanoyl-sn-glycerol
• 英文别名: 2,3-Dilauroyl-sn-glycerol；[(2R)-2-dodecanoyloxy-3-hydroxypropyl] dodecanoate
• CAS: 61475-84-1
• 化学式: C₂₇H₅₂O₅
• 分子量: 456.707
• InChiKey: OQQOAWVKVDAJOI-RUZDIDTESA-N

物化性质

• 熔点：
  45-49 °C(lit.)

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  32
• 可旋转键数：
  26
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,3-di-O-n-dodecanoyl-sn-glycerol 在 盐酸 、 (1,2-二溴-1-苯基-乙基)-膦酸 、 N,N-二异丙基乙胺 作用下， 生成 2,3-di-O-n-dodecanoyl-sn-glycer-1-yl phosphate
  参考文献：
  名称：

  Synthesis of Complex Phosphomonoesters via Monomeric Metaphosphate: The Phosphatidic Acids

  摘要：

  DOI：

  10.1055/s-1984-31015
• 作为产物：
  描述：

  1-O-benzyl-2,3-di-O-n-dodecanoyl-sn-glycerol 在 palladium on activated charcoal 氢气 作用下， 反应 20.0h， 以91%的产率得到2,3-di-O-n-dodecanoyl-sn-glycerol
  参考文献：
  名称：

  Inhibition of human erythrocyte membrane phosphatidylinositol 4-kinase by phospholipid analogues

  摘要：

  Analogues of phosphatidylinositol (Ptdlns, 1) have been synthesized to investigate the structural requirements for inhibition of a Ptdlns 4-kinase obtained from human erythrocyte membranes. While the presence of either D-1 or D-3 Stereochemistry in the inositol moiety greatly influences the degree of inhibition produced by Ptdlns analogues, the stereochemistry of the glycerol moiety is of little consequence. Neither structural feature, however, makes a significant contribution to binding affinity. Competitive inhibitory activity was found to be retained (or even enhanced) in substantially simpler analogues consisting of 1 or 2 hydrocarbon chains attached to a charged phosphate head group, such as in the phosphatidic acids, 24 and 26. The observation that the phosphatidylinositol 4-phosphate (Ptdlns 4P) and phosphatidic acid analogues (eg, 16 or 17, and 26 respectively) inhibit Ptdlns 4-kinase may suggest that such species have a regulatory role in Ptdlns turnover.

  DOI：

  10.1016/0223-5234(94)90146-5

文献信息

• Studies on the substrate specificity of purified human milk lipoprotein lipase
  作者：C. ‐S. Wang、A. Kuksis、F. Manganaro

  DOI：10.1007/bf02534942

  日期：1982.4

  The fatty acid specificity of purified human milk lipoprotein lipase was studied using the C₁₈ to C₅₄ (total acyl carbon number) saturated and the C₅₄ mono‐, di‐ and triunsaturated monoacid triacylglycerols. Kinetic determinations indicated that the medium‐chain triacylglycerols were better substrates than long‐ or very short‐chain saturated triacylglycerols. The unsaturated triacylglycerols were hydrolyzed at rates comparable to that of tricaprylin with triolein having the highest rate of hydrolysis of the unsaturated species tested. The enzyme attacked the primary ester bond much more readily than the secondary ester bond. The purified human milk lipoprotein lipase showed a preferential stereospecific lipolysis of thesn‐1‐position of the triacylglycerol molecule.

  摘要 使用 C18 至 C54（酰基总碳数）饱和和 C54 单酸、双酸和三酸三酰甘油研究了纯化人乳脂蛋白脂肪酶的脂肪酸特异性。动力学测定表明，与长链或极短链饱和三酰甘油相比，中链三酰甘油是更好的底物。不饱和三酰甘油的水解速度与三碳甘油酯的水解速度相当，其中三烯甘油酯的水解速度在所测试的不饱和三酰甘油酯中最高。该酶攻击一级酯键的速度比攻击二级酯键的速度快得多。纯化的人乳脂蛋白脂肪酶对三酰基甘油分子的sn-1位显示出优先的立体特异性脂肪分解作用。
• Synthesis of Complex Phosphomonoesters via Monomeric Metaphosphate: The Phosphatidic Acids
  作者：Fausto Ramirez、James F. Marecek

  DOI：10.1055/s-1984-31015

  日期：——
• Inhibition of human erythrocyte membrane phosphatidylinositol 4-kinase by phospholipid analogues
  作者：RC Young、CP Downes、M Jones、KJ Milliner、KK Rana、JG Ward

  DOI：10.1016/0223-5234(94)90146-5

  日期：1994.1

  Analogues of phosphatidylinositol (Ptdlns, 1) have been synthesized to investigate the structural requirements for inhibition of a Ptdlns 4-kinase obtained from human erythrocyte membranes. While the presence of either D-1 or D-3 Stereochemistry in the inositol moiety greatly influences the degree of inhibition produced by Ptdlns analogues, the stereochemistry of the glycerol moiety is of little consequence. Neither structural feature, however, makes a significant contribution to binding affinity. Competitive inhibitory activity was found to be retained (or even enhanced) in substantially simpler analogues consisting of 1 or 2 hydrocarbon chains attached to a charged phosphate head group, such as in the phosphatidic acids, 24 and 26. The observation that the phosphatidylinositol 4-phosphate (Ptdlns 4P) and phosphatidic acid analogues (eg, 16 or 17, and 26 respectively) inhibit Ptdlns 4-kinase may suggest that such species have a regulatory role in Ptdlns turnover.