5-hydroxy-2-phenyl-7-[6-O-(3,4,5-trimethoxybenzoyl)-β-D-glucopyranosyloxy]-4H-1-benzopyran-4-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: 5-hydroxy-2-phenyl-7-[6-O-(3,4,5-trimethoxybenzoyl)-β-D-glucopyranosyloxy]-4H-1-benzopyran-4-one
• 英文别名: [(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(5-hydroxy-4-oxo-2-phenylchromen-7-yl)oxyoxan-2-yl]methyl 3,4,5-trimethoxybenzoate
• 化学式: C₃₁H₃₀O₁₃
• 分子量: 610.571
• InChiKey: AMDOGVPGDZEDPB-APIIAOPOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  44
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  180
• 氢给体数：
  4
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  白杨素 在 吡啶 、 4-二甲氨基吡啶 、 氢氧化钾 、 三(3,6-二氧杂庚基)胺 、 potassium chloride 、 碳酸氢钠 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 171.0h， 生成 5-hydroxy-2-phenyl-7-[6-O-(3,4,5-trimethoxybenzoyl)-β-D-glucopyranosyloxy]-4H-1-benzopyran-4-one
  参考文献：
  名称：

  Acylated Flavone Glucosides: Synthesis, Conformational Investigation, and Complexation Properties

  摘要：

  Acylated flavonoid glycosides are ubiquitous in plants; however, the possible influence of the acyl groups on the typical properties of flavonoids is rather poorly documented. In this work, a series of chrysin (= 5,7-dihydroxyflavone) glucosides acylated with aromatic and aliphatic acid residues has been synthesized in a simple three-step procedure. Aromatic acyl groups are shown to impose folded conformations on the chrysin glucosides owing to their ability to stack on the polyphenolic nucleus. The: acyl groups may also cause significant changes in the ability of the flavonoid glucosides to bind hard metal ions and proteins, as demonstrated in this work in the case of Al3+ and bovine serum albumin.

  DOI：

  10.1002/(sici)1522-2675(19991215)82:12<2201::aid-hlca2201>3.0.co;2-4

文献信息

• Acylated Flavone Glucosides: Synthesis, Conformational Investigation, and Complexation Properties
  作者：Bertrand Alluis、Olivier Dangles

  DOI：10.1002/(sici)1522-2675(19991215)82:12<2201::aid-hlca2201>3.0.co;2-4

  日期：1999.12.15

  Acylated flavonoid glycosides are ubiquitous in plants; however, the possible influence of the acyl groups on the typical properties of flavonoids is rather poorly documented. In this work, a series of chrysin (= 5,7-dihydroxyflavone) glucosides acylated with aromatic and aliphatic acid residues has been synthesized in a simple three-step procedure. Aromatic acyl groups are shown to impose folded conformations on the chrysin glucosides owing to their ability to stack on the polyphenolic nucleus. The: acyl groups may also cause significant changes in the ability of the flavonoid glucosides to bind hard metal ions and proteins, as demonstrated in this work in the case of Al3+ and bovine serum albumin.