catechin-3-O-β-D-gluco(6-cinnamoyl)pyranoside

• 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: catechin-3-O-β-D-gluco(6-cinnamoyl)pyranoside
• 英文别名: [(2R,3S,4S,5R,6R)-6-[[(2R,3S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl]oxy]-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-phenylprop-2-enoate
• 化学式: C₃₀H₃₀O₁₂
• 分子量: 582.561
• InChiKey: JBJFEZZTGSSGBP-JRCIOFDCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  42
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  196
• 氢给体数：
  7
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 catechin-3-O-β-D-gluco(6-cinnamoyl)pyranoside 在 盐酸 作用下， 以 乙醚 、 甲醇 为溶剂， 反应 27.0h， 生成 2alpha-(3,4-二甲氧基苯基)-5,7-二甲氧基-3,4-二氢-2H-1-苯并吡喃-3beta-醇
  参考文献：
  名称：

  Cinnamoyl glucosides of catechin and dimeric procyanidins from young leaves of Inga umbellifera (Fabaceae)

  摘要：

  The rapidly growing, nearly achlorophyllous, young leaves of Inga umbellifera express high concentrations of mono and dimeric 3-O-gluco-cinnamoyl catechin/epicatechin, rare forms of substituted flavan-3-ols. Here we present structures for five novel compounds in this class: three monomers [catechin-3-O-beta-D-gluco(2-cinnamoyl)pyranoside, catechin-3-O-beta-D-gluco(6-cinnamoyl) pyranoside, catechin-3-O-beta-D-gluco(2,6-biscinnamoyl)pyranoside] and two dimeric procyanidins [catechin-3-O-beta-D-glucopyrano(4alpha-->8)-catechin-3-O-beta-D-gluco(2-cinnamoyl)pyranoside and catechin-3-O-beta-D-glucopyrano-(4alpha-->8)-epicatechin-3-O-beta-D-gluco(6-cinnamoyl)pyranoside]. The young leaves of Inga umbellifera express high concentrations of 3-O-(cinnamoyl)glucosides of catechin and epicatechin. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2003.11.012