5,7,4′-trihydroxy-3′-methoxyflavylium

• 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: 5,7,4′-trihydroxy-3′-methoxyflavylium
• 英文别名: deoxypeonidin；Luteolinidin-3'-methylaether；3-deoxypeonidin；2-(4-Hydroxy-3-methoxyphenyl)chromenylium-5,7-diol；2-(4-hydroxy-3-methoxyphenyl)chromenylium-5,7-diol
• 化学式: C₁₆H₁₃O₅
• 分子量: 285.276
• InChiKey: TZASVKGIRKMDDG-UHFFFAOYSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  3.51
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  70.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  间苯三酚 、 4-羟基-3-甲氧基肉桂醛 以 乙醇 、 水 为溶剂， 反应 96.0h， 以8%的产率得到5,7,4′-trihydroxy-3′-methoxyflavylium
  参考文献：
  名称：

  A novel reaction mechanism for the formation of deoxyanthocyanidins

  摘要：

  The synthesis of deoxyanthocyanidins from the reaction between cinnamic aldehydes (coniferaldehyde and sinapaldehyde) and phloroglucinol is reported herein. The resulting structures were characterized by visible, MS, and NMR spectroscopy. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.01.006

文献信息

• Thermodynamics, Kinetics, and Photochromism of Oaklins: A Recent Family of Deoxyanthocyanidins
  作者：André Sousa、Vesselin Petrov、Paula Araújo、Nuno Mateus、Fernando Pina、Victor de Freitas

  DOI：10.1021/jp3110216

  日期：2013.2.14

  Two oaldins guaiacylcatechinpyrylium (GCP) and syringylcatechinpyrylium (SCP) and a model compound deoxy-peonidin (DOP) were synthesized, and the rate and equilibrium constants of the respective pH dependent network of chemical reactions were calculated. In contrast to anthocyanins, the three compounds possess a small cis-trans isomerization barrier and hence the rate of the trans-chalcone formation follows a bell-shaped curve as a function of pH. The three compounds exhibit photochromism obtained by irradiation of the trans-chalcone, which, depending on pH, leads to the colored species flavylium cation and quinoidal base. The flash photolysis together with pH jumps followed by UV-vis absorption and stopped flow is a very useful tool to achieve the rate and equilibrium constants of the network of chemical reactions followed by these molecules. Oak lin compounds which are formed in wine aged in oak barrels present physical-chemical properties more similar to simpler deoxyanthocyanidins rather than anthocyanins and may play a significant role in color changes observed in wine aging. Given their higher stability, they may be regarded as potential food colorants.
• A novel reaction mechanism for the formation of deoxyanthocyanidins
  作者：André Sousa、Nuno Mateus、Victor de Freitas

  DOI：10.1016/j.tetlet.2012.01.006

  日期：2012.3

  The synthesis of deoxyanthocyanidins from the reaction between cinnamic aldehydes (coniferaldehyde and sinapaldehyde) and phloroglucinol is reported herein. The resulting structures were characterized by visible, MS, and NMR spectroscopy. (C) 2012 Elsevier Ltd. All rights reserved.