8-vinyl-(+)-catechin | 388089-50-7

• 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: 8-vinyl-(+)-catechin
• 英文别名: (2R,3S)-2-(3,4-dihydroxyphenyl)-8-ethenyl-3,4-dihydro-2H-chromene-3,5,7-triol
• CAS: 388089-50-7
• 化学式: C₁₇H₁₆O₆
• 分子量: 316.31
• InChiKey: NSZXIUNKSQZIQS-JKSUJKDBSA-N

物化性质

• 沸点：
  645.4±55.0 °C(Predicted)
• 密度：
  1.519±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  110
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  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

• Synthesis and Structural Characterization of Two Diasteroisomers of Vinylcatechin Dimers
  作者：Luís Cruz、Natércia F. Brás、Natércia Teixeira、Ana Fernandes、Nuno Mateus、Maria João Ramos、José Rodríguez-Borges、Victor de Freitas

  DOI：10.1021/jf901608n

  日期：2009.11.11

  (9S,11R)- and (9R,11S)-vinylcatechin dimers, were obtained, and their structures were characterized by mass spectrometry (MS) and nuclear magnetic resonance (NMR). These compounds were also found to occur in reactions between (+)-catechin and acetaldehyde. The identification of different conformations of both isomers was achieved by computational methods. The enthalpy values calculated suggest that

  8-乙烯基黄烷-3-醇在文献中被描述为涉及葡萄酒或模型样溶液中吡喃花青素形成机理的中间化合物。8-乙烯基-（+）-儿茶素在溶液中表现出非常不稳定的状态，并显示出很高的反应活性，在模型酒溶液中经历了异常的酸催化二聚作用，涉及到新的二氢吡喃环的形成。两个非对映异构体（9 S，11 R）-和（9 R，11 S获得了）-乙烯基儿茶素二聚体，并通过质谱（MS）和核磁共振（NMR）对它们的结构进行了表征。还发现这些化合物发生在（+）-儿茶素和乙醛之间的反应中。两种异构体不同构象的鉴定是通过计算方法实现的。计算的焓值表明，与异构体（9 R，11 S）相比，异构体（9 S，11 R）更稳定并且在热力学上有利于其形成。
• 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).