(+)-3,5,7,3'-tetra-O-acetylcatechin | 1209469-08-8

• 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: (+)-3,5,7,3'-tetra-O-acetylcatechin
• CAS: 1209469-08-8
• 化学式: C₂₃H₂₂O₁₀
• 分子量: 458.422
• InChiKey: FJAOSOWQOPHZIY-XZOQPEGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.78
• 重原子数：
  33.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  134.66
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为产物：
  描述：

  五乙酸儿茶素酯 在 咪唑 、 苯硫酚 作用下， 以 N-甲基吡咯烷酮 为溶剂， 生成 (+)-3,5,7,3'-tetra-O-acetylcatechin 、 (+)-3,5,7,4'-tetra-O-acetylcatechin 、 (+)-3,7,3',4'-tetra-O-acetylcatechin
  参考文献：
  名称：

  Catechin Glucosides: Occurrence, Synthesis, and Stability

  摘要：

  Catechins are flavonoids with suggested health benefits, but are unstable during storage, processing and, after ingestion, during gut transit. We hypothesized that catechin glucosides, which occur in various plants, could be more stable than unsubstituted catechin, and additionally be deglucosylated in the gut and so act to deliver catechin in a form able to be absorbed. (+)-Catechin O-glucosides from various sources have been used in the course of this investigation. (+)-Catechin 3'-O-beta-D-glucopyranoside (C3'G), (+)-catechin 5-O-beta-D-glucopyranoside (C5G), and (+)-catechin 3-O-beta-D-glucopyranoside (C3G) were chemically synthesized. (+)-Catechin 4'-O-beta-D-glucopyranoside (C4'G) and (+)-catechin 7-O-beta-D-glucopyranoside (C7G) were prepared enzymically using preparations from lentil and barley. In general, but with some exceptions, the (+)-catechin glucosides were more stable between pH 4 and 8 than (+)-catechin, with C3'G exhibiting greatest stability. The intestinal metabolism of (+)-catechin and all (+)-catechin glucosides in the gut was determined by perfusion of rat intestine in vivo. C3'G and C5G were extensively deglycosylated in the gut, and C3'G showed greatest apparent "absorption" as calculated by the difference between effluent and influent. The results show the potential of catechin glucosides, especially C3'G, as more stable prescursors of catechin.

  DOI：

  10.1021/jf9034095