1-O-(2-cyclohexylethanoyl)-2-O-[6-O-(2-cyclohexylethanoyl)-β-D-galactopyranosyl]-sn-glycerol | 923931-48-0

• 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-O-(2-cyclohexylethanoyl)-2-O-[6-O-(2-cyclohexylethanoyl)-β-D-galactopyranosyl]-sn-glycerol
• CAS: 923931-48-0
• 化学式: C₂₅H₄₂O₁₀
• 分子量: 502.602
• InChiKey: SZIPKFWIHOUBRB-FJJHSCLASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  35.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  151.98
• 氢给体数：
  4.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  1-O-(2-cyclohexylethanoyl)-2-O-[6-O-(2-cyclohexylethanoyl)-β-D-galactopyranosyl]-sn-glycerol 在 Aspergillus oryzae β-galactosidase 、 对甲苯磺酸 作用下， 以 丙酮 为溶剂， 生成 Cyclohexyl-acetic acid (S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester
  参考文献：
  名称：

  Cyclic and branched acyl chain galactoglycerolipids and their effect on anti-tumor-promoting activity

  摘要：

  Fifteen new galactoglycerolipid analogues, in which one or two branched, alicyclic or aromatic acyl chains are linked to 2-O-beta-D-galacto-sylglycerol (6'-position or 1,6' positions), were prepared and tested for their anti-tumor-promoting activity using a short-term in vitro assay for Epstein-Barr virus early antigen (EBV-EA) activation. All compounds were active in inhibiting the EBV activation promoted by the tumor promoter 12-O-tetradecanoylphorbol-13-acetate (TPA), the branched compounds resulting in the most active glycoglycerolipid analogues of the series. The branched 2-O-[6-O-(3-methylbutanoyl)-beta-D-galactopyranosyll-sn-glyceroI (1a) and the structurally related alicyclic 2-O-[6-O-(2-cyclohexylethanoyl)-beta-D-galactopyranosyl]-sn-glycerol (1d), when tested in an in vivo two-stage carcinogenesis test, exhibited inhibitory effects on mouse skin tumor promotion. (c) 2006 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.07.007
• 作为产物：
  描述：

  Cyclohexyl-acetic acid 2,2,2-trifluoro-ethyl ester 、 2-O-(β-D-galactopyranosyl)-glycerol 在 吡啶 、 Pseudomonas cepacia lipase 作用下， 反应 300.0h， 以6%的产率得到1-O-(2-cyclohexylethanoyl)-2-O-[6-O-(2-cyclohexylethanoyl)-β-D-galactopyranosyl]-sn-glycerol
  参考文献：
  名称：

  Cyclic and branched acyl chain galactoglycerolipids and their effect on anti-tumor-promoting activity

  摘要：

  Fifteen new galactoglycerolipid analogues, in which one or two branched, alicyclic or aromatic acyl chains are linked to 2-O-beta-D-galacto-sylglycerol (6'-position or 1,6' positions), were prepared and tested for their anti-tumor-promoting activity using a short-term in vitro assay for Epstein-Barr virus early antigen (EBV-EA) activation. All compounds were active in inhibiting the EBV activation promoted by the tumor promoter 12-O-tetradecanoylphorbol-13-acetate (TPA), the branched compounds resulting in the most active glycoglycerolipid analogues of the series. The branched 2-O-[6-O-(3-methylbutanoyl)-beta-D-galactopyranosyll-sn-glyceroI (1a) and the structurally related alicyclic 2-O-[6-O-(2-cyclohexylethanoyl)-beta-D-galactopyranosyl]-sn-glycerol (1d), when tested in an in vivo two-stage carcinogenesis test, exhibited inhibitory effects on mouse skin tumor promotion. (c) 2006 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.07.007