8-(3,3',4',5,7-pentahydroxyflavan-4-yl)-3,3',4',5,7-pentahydroxyflavan

• 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-(3,3',4',5,7-pentahydroxyflavan-4-yl)-3,3',4',5,7-pentahydroxyflavan
• 英文别名: procyanidin B4；(2R,3R)-2-(3,4-dihydroxyphenyl)-8-[(2R,3S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-4-yl]-3,4-dihydro-2H-chromene-3,5,7-triol
• 化学式: C₃₀H₂₆O₁₂
• 分子量: 578.529
• InChiKey: XFZJEEAOWLFHDH-NMHICJPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  42
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  221
• 氢给体数：
  10
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  4-羟基-3-甲氧基肉桂醛 、 8-(3,3',4',5,7-pentahydroxyflavan-4-yl)-3,3',4',5,7-pentahydroxyflavan 在 间苯三酚 作用下， 以 乙醇 、 水 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and Structural Characterization of Oaklin–Catechins

  摘要：

  Condensation reactions of procyanidin diner B4 with two representative oak wood cinnamic aldehydes (coniferaldehyde and sinapaldehyde) were conducted in winelike model solutions. Coniferaldehyde led to the formation of guaiacylcatechin-pyrylium-catechin (GCP-catechin, 737 m/z), whereas sinapaldehyde led to the formation of syringylcatechin-pyrylium-catechin (SCP-catechin, 767 m/z). The former was also structurally characterized by 1D and 2D NMR, allowing an elucidation of the formation mechanism of these oaklin-catechin adducts and demonstrating the importance of procyanidins in the formation of colored compounds through the reaction with cinnamic aldehydes extracted from oaks during storage.

  DOI：

  10.1021/jf204408p

文献信息

• Synthesis and Structural Characterization of Oaklin–Catechins
  作者：André Sousa、Ana Fernandes、Nuno Mateus、Victor De Freitas

  DOI：10.1021/jf204408p

  日期：2012.2.15

  Condensation reactions of procyanidin diner B4 with two representative oak wood cinnamic aldehydes (coniferaldehyde and sinapaldehyde) were conducted in winelike model solutions. Coniferaldehyde led to the formation of guaiacylcatechin-pyrylium-catechin (GCP-catechin, 737 m/z), whereas sinapaldehyde led to the formation of syringylcatechin-pyrylium-catechin (SCP-catechin, 767 m/z). The former was also structurally characterized by 1D and 2D NMR, allowing an elucidation of the formation mechanism of these oaklin-catechin adducts and demonstrating the importance of procyanidins in the formation of colored compounds through the reaction with cinnamic aldehydes extracted from oaks during storage.