5-((2R,3S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxychroman-8-yl)-8-hydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)pyrano[4,3,2-de]chromen-1-ium | 415692-44-3

• 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: 5-((2R,3S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxychroman-8-yl)-8-hydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)pyrano[4,3,2-de]chromen-1-ium
• CAS: 415692-44-3
• 化学式: C₄₀H₃₇O₁₈
• 分子量: 805.723
• InChiKey: MEHKGXJZDJNJRC-PSRZXQIRSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  2.74
• 重原子数：
  58.0
• 可旋转键数：
  8.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  289.21
• 氢给体数：
  11.0
• 氢受体数：
  17.0

反应信息

• 作为产物：
  描述：

  锦葵素-3-O-葡萄糖苷 、 8-vinyl-(+)-catechin 以 乙醇 、 水 为溶剂， 生成 5-((2R,3S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxychroman-8-yl)-8-hydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)pyrano[4,3,2-de]chromen-1-ium
  参考文献：
  名称：

  Establishment of the Chemical Equilibria of Different Types of Pyranoanthocyanins in Aqueous Solutions: Evidence for the Formation of Aggregation in Pyranomalvidin-3-O-coumaroylglucoside-(+)-catechin

  摘要：

  The chemical equilibria of the pyranomalvidin-3-glucosides linked to (+)-catechin, (-)-epicatechin, and catechol moieties (and the respective coumaroylglucoside Compounds) were established by means of UV-vis spectroscopy. The conjugated double bonds among pyranic rings C and D provide a higher electronic delocalization that prevents the nucleophilic attack of water at position 2. Consequently, besides flavylium cation (AH(+)), the bases A, A(-), and A(2-) have been identified by increasing pH, and the respective acidity constants were determined by spectrophotometry. The formation of dimers at higher concentration was observed for pyranomalvidin-3-O-coumaroylglucoside-(+)-catechin, and the respective data treated by the exciton model suggests the for-nation of a chiller where the monomers form J-type aggregates with the dipolar moments in opposite directions and rotated by 174 degrees at a distance of 5.2 angstrom (from the center).

  DOI：

  10.1021/jp1045673

文献信息

• Establishment of the Chemical Equilibria of Different Types of Pyranoanthocyanins in Aqueous Solutions: Evidence for the Formation of Aggregation in Pyranomalvidin-3-<i>O</i>-coumaroylglucoside-(+)-catechin
  作者：Luís Cruz、Vesselin Petrov、Natércia Teixeira、Nuno Mateus、Fernando Pina、Victor de Freitas

  DOI：10.1021/jp1045673

  日期：2010.10.21

  The chemical equilibria of the pyranomalvidin-3-glucosides linked to (+)-catechin, (-)-epicatechin, and catechol moieties (and the respective coumaroylglucoside Compounds) were established by means of UV-vis spectroscopy. The conjugated double bonds among pyranic rings C and D provide a higher electronic delocalization that prevents the nucleophilic attack of water at position 2. Consequently, besides flavylium cation (AH(+)), the bases A, A(-), and A(2-) have been identified by increasing pH, and the respective acidity constants were determined by spectrophotometry. The formation of dimers at higher concentration was observed for pyranomalvidin-3-O-coumaroylglucoside-(+)-catechin, and the respective data treated by the exciton model suggests the for-nation of a chiller where the monomers form J-type aggregates with the dipolar moments in opposite directions and rotated by 174 degrees at a distance of 5.2 angstrom (from the center).