(R)-mesquitol-[5->8]-catechin

• 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: (R)-mesquitol-[5->8]-catechin
• 英文别名: (S)-mesquitol-[5->8]-catechin；(2R,3S)-2-(3,4-dihydroxyphenyl)-5-[(2R,3S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-8-yl]-3,4-dihydro-2H-chromene-3,7,8-triol
• 化学式: C₃₀H₂₆O₁₂
• 分子量: 578.529
• InChiKey: JGOTXORLVJKLDL-KBJUPQRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  42
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  221
• 氢给体数：
  10
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  2H-1-苯并吡喃-3,7,8-三醇,2-(3,4-二羟基苯基)-3,4-二氢-,(2R,3S)- 、 儿茶提取物 在 phosphate buffer 、 tyrosinase 作用下， 以 水 为溶剂， 生成 (R)-mesquitol-[5->8]-catechin
  参考文献：
  名称：

  Tyrosinase catalysed biphenyl construction from flavan-3-ol substrates

  摘要：

  Mushroom tyrosinase catalysed oxidation of three flavan-3-ols, viz. catechin, fisetinidol and mesquitol, was conducted to construct biphenyl bonds. Exposure of the flavan-3-ols to tyrosinase and subsequent trapping of the o-quinone intermediates resulted in the formation of novel flavan-3-ol derivatives, the structures of which were elucidated by mono- and two-dimensional 1H-NMR experiments. Application of the methodology resulted in the improved synthesis of the natural flavan-3-ol dimer, mesquitol-[5-->8]-catechin, previously isolated from Prosopis glandulosa.

  DOI：

  10.1016/s0031-9422(99)00476-8

文献信息

• Tyrosinase catalysed biphenyl construction from flavan-3-ol substrates
  作者：Werner Janse van Rensburg、Daneel Ferreira、Elfranco Malan、Jacobus A. Steenkamp

  DOI：10.1016/s0031-9422(99)00476-8

  日期：2000.1

  Mushroom tyrosinase catalysed oxidation of three flavan-3-ols, viz. catechin, fisetinidol and mesquitol, was conducted to construct biphenyl bonds. Exposure of the flavan-3-ols to tyrosinase and subsequent trapping of the o-quinone intermediates resulted in the formation of novel flavan-3-ol derivatives, the structures of which were elucidated by mono- and two-dimensional 1H-NMR experiments. Application of the methodology resulted in the improved synthesis of the natural flavan-3-ol dimer, mesquitol-[5-->8]-catechin, previously isolated from Prosopis glandulosa.