malvidin 3-O-(6''-coumaroyl)glucoside | 158189-28-7

• 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: malvidin 3-O-(6''-coumaroyl)glucoside
• 英文别名: Malvidin 3-(6''-p-coumarylglucoside)；[(2R,3S,4S,5R,6S)-6-[5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)chromenylium-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
• CAS: 158189-28-7
• 化学式: C₃₂H₃₁O₁₄
• 分子量: 639.59
• InChiKey: HXQOVGDXCHFLOP-KWNZYCHBSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  2.66
• 重原子数：
  46
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  206
• 氢给体数：
  7
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  乙烯氧基三甲基硅烷 、 malvidin 3-O-(6''-coumaroyl)glucoside 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 以30%的产率得到malvidin-3-O-(6-O-coumaroyl)glucoside acetaldehyde
  参考文献：
  名称：

  A novel synthetic pathway to vitisin B compounds

  摘要：

  The hemi-synthesis of vitisin B compounds is described herein for the first time through a new, simple and Suitable reaction of malvidin-3-glucoside and malvidin-3-O-coumaroylglucoside with vinyloxy-trimethylsilane. The obtained compounds were identified by LC/DAD-MS and fully characterized by NMR analysis for the first time. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.04.072

文献信息

• Isolation and Structural Characterization of New Anthocyanin-Derived Yellow Pigments in Aged Red Wines
  作者：Jingren He、Celestino Santos-Buelga、Artur M. S. Silva、Nuno Mateus、Victor de Freitas

  DOI：10.1021/jf062325q

  日期：2006.12.1

  structures of these pigments correspond to methyl-linked pyranomalvidin 3-glucoside and its respective coumaroyl glucoside derivative. They were shown to arise from the reaction between acetoacetic acid and genuine grape anthocyanins. Isolation and NMR identification using 1D and 2D NMR techniques are reported for the first time for this new family of anthocyanin-derived yellow pigments occurring in red

  通过TSK Toyopearl HW-40（s）凝胶色谱法从陈年的Port红酒中检测并分离出两种具有独特光谱特征的黄色颜料，并通过紫外可见分光光度法，1H NMR和13C NMR以及质谱（LC）对其进行了表征。 -ESI / MS）。这些颜料的UV-vis光谱显示在478 nm处有最大吸收，这与原始葡萄花色苷和其他吡喃花青素的吸收相比显着变色，在酸性溶液中显示出更多的黄色调。这些颜料的结构对应于甲基连接的吡喃马维丁3-葡糖苷及其各自的香豆酰基葡糖苷衍生物。已显示它们是由乙酰乙酸与纯正的葡萄花色苷之间的反应产生的。
• 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).