1-O-decanoyl-2-O-(6-O-decanoyl-β-D-glucopyranosyl)-sn-glycerol

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: 1-O-decanoyl-2-O-(6-O-decanoyl-β-D-glucopyranosyl)-sn-glycerol
• 英文别名: [(2R,3S,4S,5R,6R)-6-[(2S)-1-decanoyloxy-3-hydroxypropan-2-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl decanoate
• 化学式: C₂₉H₅₄O₁₀
• 分子量: 562.742
• InChiKey: IUTSSJSQFHXEDD-SAQJKEKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  39
• 可旋转键数：
  25
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  152
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  2,2,2-trifluoroethyl decanoate 、 1,3-二羟基-2-丙基吡喃己糖苷 在 Pseudomonas cepacia lipase on Celite 作用下， 以 吡啶 为溶剂， 反应 20.0h， 以88%的产率得到1-O-decanoyl-2-O-(6-O-decanoyl-β-D-glucopyranosyl)-sn-glycerol
  参考文献：
  名称：

  Diesters of glycosylglycerols active in cancer chemoprevention

  摘要：

  Enzymatic transesterification, mediated by Pseudomonas cepacia lipase (lipase PS), led to the pure 1,6'-diacylderivatives of 2-O-beta -D-glucosyl-sn-glycerol and 2-O-beta -D-galactosyl-sn-glycerol, the acyl Chains being derived from short-medium length fatty acids. A study of the in vitro inhibitory effects of these diacylderivatives on Epstein-Barr virus early antigen activation induced by the tumour promoter 12-O-tetradecanoylphorbol-13-acetate revealed that maximum activity was reached for the hexanoyl chain and that the introduction of a second acyl chain did not significantly modify the inhibitory potential referring to the corresponding 1-or 6'-monoesters. (C) 2001 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(01)01261-2

文献信息

• Diesters of glycosylglycerols active in cancer chemoprevention
  作者：Diego Colombo、Federica Compostella、Fiamma Ronchetti、Antonio Scala、Harukuni Tokuda、Hoyoku Nishino

  DOI：10.1016/s0223-5234(01)01261-2

  日期：2001.8

  Enzymatic transesterification, mediated by Pseudomonas cepacia lipase (lipase PS), led to the pure 1,6'-diacylderivatives of 2-O-beta -D-glucosyl-sn-glycerol and 2-O-beta -D-galactosyl-sn-glycerol, the acyl Chains being derived from short-medium length fatty acids. A study of the in vitro inhibitory effects of these diacylderivatives on Epstein-Barr virus early antigen activation induced by the tumour promoter 12-O-tetradecanoylphorbol-13-acetate revealed that maximum activity was reached for the hexanoyl chain and that the introduction of a second acyl chain did not significantly modify the inhibitory potential referring to the corresponding 1-or 6'-monoesters. (C) 2001 Editions scientifiques et medicales Elsevier SAS.