(R)-8,8-methylmethine-catechin-malvidin 3-O-glucoside

• 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: (R)-8,8-methylmethine-catechin-malvidin 3-O-glucoside
• 英文别名: (2R,3S)-8-[(1R)-1-[5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromenylium-8-yl]ethyl]-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
• 化学式: C₄₀H₄₁O₁₈
• 分子量: 809.755
• InChiKey: OWEZHPRMUFSMFC-IBGSEJEXSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  58
• 可旋转键数：
  9
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  290
• 氢给体数：
  12
• 氢受体数：
  17

反应信息

• 作为产物：
  描述：

  锦葵素-3-O-葡萄糖苷 、 乙醛 、 儿茶提取物 在 溶剂黄146 作用下， 反应 48.0h， 生成 (R)-8,8-methylmethine-catechin-malvidin 3-O-glucoside 、 (S)-8,8-methylmethine-catechin-malvidin 3-O-glucoside
  参考文献：
  名称：

  UV−Visible Spectroscopic Investigation of the 8,8-Methylmethine Catechin-malvidin 3-Glucoside Pigments in Aqueous Solution:  Structural Transformations and Molecular Complexation with Chlorogenic Acid

  摘要：

  The physicochemical properties of 8,8-methylmethine catechin-malvidin 3-O-glucoside isomers, commonly referred to as catechin-ethyl-malvidin 3-O-glucoside, have been studied in aqueous solutions and compared with those of the parent anthocyanin (malvidin 3-O-glucoside). The hydration and acidity constants (pK(h) and pK(a)) of the catechin-ethyl-malvidin 3-O-glucoside pigments and malvidin 3-O-glucoside were determined by UV-visible spectroscopic measurements. The ethyl-linked catechin-malvidin 3-O-glucoside pigments present higher stability toward hydration than the parent anthocyanin. The high resistance of these ethyl-linked pigments toward the hydration is related to the self-association that offers optimal protection from the nucleophilic attack of water. Moreover, the ethyl link may confer to the molecule enough flexibility to undergo intramolecular interaction, further protecting it from hydration and bisulfite discoloration. In the wine pH range (3.2-4.0), due to the low pK(a) and high pK(h) values, the ethyl-linked pigments are present as colored forms (flavylium cation and quinonoid bases).

  DOI：

  10.1021/jf0516989

文献信息

• UV−Visible Spectroscopic Investigation of the 8,8-Methylmethine Catechin-malvidin 3-Glucoside Pigments in Aqueous Solution:  Structural Transformations and Molecular Complexation with Chlorogenic Acid
  作者：Montserrat Dueñas、Erika Salas、Véronique Cheynier、Olivier Dangles、Hélène Fulcrand

  DOI：10.1021/jf0516989

  日期：2006.1.1

  The physicochemical properties of 8,8-methylmethine catechin-malvidin 3-O-glucoside isomers, commonly referred to as catechin-ethyl-malvidin 3-O-glucoside, have been studied in aqueous solutions and compared with those of the parent anthocyanin (malvidin 3-O-glucoside). The hydration and acidity constants (pK(h) and pK(a)) of the catechin-ethyl-malvidin 3-O-glucoside pigments and malvidin 3-O-glucoside were determined by UV-visible spectroscopic measurements. The ethyl-linked catechin-malvidin 3-O-glucoside pigments present higher stability toward hydration than the parent anthocyanin. The high resistance of these ethyl-linked pigments toward the hydration is related to the self-association that offers optimal protection from the nucleophilic attack of water. Moreover, the ethyl link may confer to the molecule enough flexibility to undergo intramolecular interaction, further protecting it from hydration and bisulfite discoloration. In the wine pH range (3.2-4.0), due to the low pK(a) and high pK(h) values, the ethyl-linked pigments are present as colored forms (flavylium cation and quinonoid bases).