epitheaflagallin-3-O-gallate

• 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: epitheaflagallin-3-O-gallate
• 英文别名: [(2S,3S)-5,7-dihydroxy-2-(2,3,4,5-tetrahydroxy-6-oxobenzo[7]annulen-8-yl)-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate
• 化学式: C₂₇H₂₀O₁₃
• 分子量: 552.448
• InChiKey: CMGRMMSVGCHWOK-FNZWTVRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.45
• 重原子数：
  40.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  234.67
• 氢给体数：
  9.0
• 氢受体数：
  13.0

反应信息

• 作为产物：
  描述：

  (-)-表没食子儿茶素没食子酸酯 在 Japanese pear fruit homogenate 、 2-巯基乙醇 作用下， 以 乙醇 为溶剂， 反应 21.0h， 以3.236 g的产率得到theasinensin A
  参考文献：
  名称：

  A Novel Black Tea Pigment and Two New Oxidation Products of Epigallocatechin-3-O-gallate

  摘要：

  During tea fermentation, oxidation-reduction dismutation of a number of quinone metabolites of tea catechins yields numerous minor products, which make it difficult to separate and purify black tea polyphenols. In this study, epigallocatechin-3-O-gallate was enzymatically oxidized and then the unstable quinone metabolites in the oxidation mixture were hydrogenated with 2-mercaptoethanol to reduce production of inseparable minor dismutation products. As a result, three new oxidation products including a new black tea pigment were isolated, and their structures were determined based on chemical and spectroscopic data. Dehydrotheasinensin AQ is a new reddish-orange pigment with a 1,2-diketone structure, and its presence in commercial black tea was confirmed. In addition, a new quinone dimer with a complex caged structure and a trimer of epigallocatechin-3-O-gallate were also isolated and their production mechanisms are proposed. The presence of this trimer suggested participation of galloyl quinones in production of minor polyphenols in black tea.

  DOI：

  10.1021/jf0512656