octadecyl 3,4,5-tribenzyloxybenzoate | 1063201-10-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: octadecyl 3,4,5-tribenzyloxybenzoate
• 英文别名: 3,4,5-tris-benzyloxy-benzoic acid octadecyl ester；3,4,5-Tris-benzyloxy-benzoesaeure-octadecylester
• CAS: 1063201-10-4
• 化学式: C₄₆H₆₀O₅
• 分子量: 692.979
• InChiKey: UWNDMYWTRYHVSP-UHFFFAOYSA-N

物化性质

• 沸点：
  745.3±50.0 °C(Predicted)
• 密度：
  1.046±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  12.84
• 重原子数：
  51.0
• 可旋转键数：
  27.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  octadecyl 3,4,5-tribenzyloxybenzoate 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 以97%的产率得到没食子酸十八酯
  参考文献：
  名称：

  Antiproliferative and apoptosis-inducing activities of alkyl gallate and gallamide derivatives related to (−)-epigallocatechin gallate

  摘要：

  Green tea and (-)-epigallocatechin gallate (EGCG: one of the main components of green tea) are reported to have cancer-preventive activity in humans. A previous SAR study of EGCG and derivatives indicated that a galloyl group is essential for the activity. To test this hypothesis, we synthesized various alkyl gallate and gallamide derivatives and evaluated their antiproliferative effects on human leukemia HL-60 cells. Dodecyl 3,4,5-trihydroxybenzoate (6c) showed the most potent activity, being more potent than EGCG. To clarify the molecular mechanism of the antiproliferative action, we investigated the effects of 6c on various factors. Compound 6c was found to induce apoptosis mediated by endoplasmic reticulum (ER)-stress-related caspase-12. Upregulation of gadd-153, an ER-stress marker protein, was also observed. These results indicate that 6c induced apoptosis via the ER-stress-related pathway. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.07.063
• 作为产物：
  描述：

  硬脂醇 、 3,4,5-tris(benzyloxy)benzoyl chloride 生成 octadecyl 3,4,5-tribenzyloxybenzoate
  参考文献：
  名称：

  没食子酸的高级脂肪醇酯。

  摘要：

  DOI：

  10.1021/ja01207a043