4-bromo-epigallocatechin gallate peracetate | 329904-37-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 4-bromo-epigallocatechin gallate peracetate
• CAS: 329904-37-2
• 化学式: C₃₈H₃₃BrO₁₉
• 分子量: 873.573
• InChiKey: UQYRBUBAUPMVDI-HUPSOOMJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.88
• 重原子数：
  58.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  245.93
• 氢给体数：
  0.0
• 氢受体数：
  19.0

反应信息

• 作为反应物：
  描述：

  4-bromo-epigallocatechin gallate peracetate 在 甲醇 、 硼氘化钠 作用下， 反应 6.0h， 以52%的产率得到[4-2H]-epigallocatechin gallate
  参考文献：
  名称：

  Synthesis of (−)-[4-³H]Epigallocatechin Gallate and Its Metabolic Fate in Rats after Intravenous Administration

  摘要：

  Because a great deal of attention has been focused on the metabolism of (-)-epigallocatechin gallate (EGCg), quantitative analysis of this compound is required. For this purpose we developed a method of chemical synthesis of [4-H-3]EGCg. Synthesized [4-H-3]EGCg showed 99.5% radiochemical purity and a specific activity of 13 Ci/mmol. To clarify the excretion route of EGCg, the radioactivity levels of bile and urine were quantified after intravenous administration of [4-H-3]EGCg to bile-duct-cannulated rats. Results showed that the radioactivity of the bile sample excreted within 48 h accounted for 77.0% of the dose, whereas only 2.0% of the dose was recovered in the urine. The excretion ratio of bile to urine was calculated to be about 97:3. These results clearly showed that bile was the major excretion route of EGCg. Time-course analysis of the radioactivity in blood was also performed to estimate the pharmacokinetic parameters following intravenous administration of [4-H-3]EGCg. In addition, EGCg metabolites excreted in the bile within 4 h after the intravenous dose of [4-H-3]EGCg were analyzed by HPLC. The results showed that 4',4"-di-O-methyl-EGCg was present in the conjugated form and made up about 14.7% of the administered radioactivity.

  DOI：

  10.1021/jf0011236
• 作为产物：
  描述：

  (-)-表没食子儿茶素没食子酸酯八乙酸酯 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 以 四氯化碳 为溶剂， 反应 1.0h， 以46%的产率得到4-bromo-epigallocatechin gallate peracetate
  参考文献：
  名称：

  Synthesis of (−)-[4-³H]Epigallocatechin Gallate and Its Metabolic Fate in Rats after Intravenous Administration

  摘要：

  Because a great deal of attention has been focused on the metabolism of (-)-epigallocatechin gallate (EGCg), quantitative analysis of this compound is required. For this purpose we developed a method of chemical synthesis of [4-H-3]EGCg. Synthesized [4-H-3]EGCg showed 99.5% radiochemical purity and a specific activity of 13 Ci/mmol. To clarify the excretion route of EGCg, the radioactivity levels of bile and urine were quantified after intravenous administration of [4-H-3]EGCg to bile-duct-cannulated rats. Results showed that the radioactivity of the bile sample excreted within 48 h accounted for 77.0% of the dose, whereas only 2.0% of the dose was recovered in the urine. The excretion ratio of bile to urine was calculated to be about 97:3. These results clearly showed that bile was the major excretion route of EGCg. Time-course analysis of the radioactivity in blood was also performed to estimate the pharmacokinetic parameters following intravenous administration of [4-H-3]EGCg. In addition, EGCg metabolites excreted in the bile within 4 h after the intravenous dose of [4-H-3]EGCg were analyzed by HPLC. The results showed that 4',4"-di-O-methyl-EGCg was present in the conjugated form and made up about 14.7% of the administered radioactivity.

  DOI：

  10.1021/jf0011236