(2R,2'R,3S,3'S)-8,8'-(ethane-1,1-diyl)bis(2-(3,4-dihydroxyphenyl)chromane-3,5,7-triol) | 205645-53-0

• 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: (2R,2'R,3S,3'S)-8,8'-(ethane-1,1-diyl)bis(2-(3,4-dihydroxyphenyl)chromane-3,5,7-triol)
• CAS: 205645-53-0
• 化学式: C₃₂H₃₀O₁₂
• 分子量: 606.583
• InChiKey: YAJCVOAVVMHKQC-SRPPIYJJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.56
• 重原子数：
  44.0
• 可旋转键数：
  4.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  220.76
• 氢给体数：
  10.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  2-巯基乙醇 、 (2R,2'R,3S,3'S)-8,8'-(ethane-1,1-diyl)bis(2-(3,4-dihydroxyphenyl)chromane-3,5,7-triol) 在 盐酸 作用下， 生成 、 儿茶提取物
  参考文献：
  名称：

  Competition between (+)-Catechin and (−)-Epicatechin in Acetaldehyde-Induced Polymerization of Flavanols

  摘要：

  The reactions of (+)-catechin and (-)-epicatechin in the presence of acetaldehyde were studied in model solution systems. When incubated separately with acetaldehyde and at pH values varying from 2.2 to 4.0, reactions were faster with (-)-epicatechin than with (+)-catechin. In mixtures containing both (+)-catechin and (-)-epicatechin with acetaldehyde, new compounds besides the homogeneous bridged derivatives were detected. These compounds were concluded to be he heteroligomers consisting of (+)-catechin and (-)-epicatechin linked with an ethyl bridge. In this case, the reaction of (-)-epicatechin was faster than that of (+)-catechin. This was also observed in solutions containing the two flavanols and the (+)-catechin-ethanol intermediate. Under these conditions, the homogeneous (+)-catechin bridged dimers and heterogeneous dimers were obtained by action of the intermediate on (+)-catechin and (-)-epicatechin, respectively. In addition, the homogeneous (-)-epicatechin ethyl-bridged dimers were also detected, showing that ethyl linkages underwent depolymerization and recombination reactions.

  DOI：

  10.1021/jf980628h
• 作为产物：
  描述：

  6-8 (ethane-1,1-diyl) di(+)-catechin 在 盐酸 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 生成 (2R,2'R,3S,3'S)-8,8'-(ethane-1,1-diyl)bis(2-(3,4-dihydroxyphenyl)chromane-3,5,7-triol)
  参考文献：
  名称：

  Competition between (+)-Catechin and (−)-Epicatechin in Acetaldehyde-Induced Polymerization of Flavanols

  摘要：

  The reactions of (+)-catechin and (-)-epicatechin in the presence of acetaldehyde were studied in model solution systems. When incubated separately with acetaldehyde and at pH values varying from 2.2 to 4.0, reactions were faster with (-)-epicatechin than with (+)-catechin. In mixtures containing both (+)-catechin and (-)-epicatechin with acetaldehyde, new compounds besides the homogeneous bridged derivatives were detected. These compounds were concluded to be he heteroligomers consisting of (+)-catechin and (-)-epicatechin linked with an ethyl bridge. In this case, the reaction of (-)-epicatechin was faster than that of (+)-catechin. This was also observed in solutions containing the two flavanols and the (+)-catechin-ethanol intermediate. Under these conditions, the homogeneous (+)-catechin bridged dimers and heterogeneous dimers were obtained by action of the intermediate on (+)-catechin and (-)-epicatechin, respectively. In addition, the homogeneous (-)-epicatechin ethyl-bridged dimers were also detected, showing that ethyl linkages underwent depolymerization and recombination reactions.

  DOI：

  10.1021/jf980628h

文献信息

• Role of Aldehydic Derivatives in the Condensation of Phenolic Compounds with Emphasis on the Sensorial Properties of Fruit-Derived Foods
  作者：Nour-Eddine Es-Safi、Véronique Cheynier、Michel Moutounet

  DOI：10.1021/jf025503y

  日期：2002.9.1

  The reactions between (epi)catechin mavidin 3 O-glucoside and some aldehydes were investigated by LC/DAD and LC/ESI MS analysis. The obtained results showed that the acetaldehyde mediated condensation occurred more generally and glyoxylic acid furfural and 5 (hydroxymethyl)furfural (HMF) react in the same way in the first stages of the reactions. In terms of reactivity, reactions were faster with acetaldehyde than with glyoxylic acid furfural or HMF where the reactions were slower. In the case of acetaldehyde, the obtained purple derivatives were more predominant and stable than the colorless adducts and no xanthylium salt was detected. Interactions involving glyoxylic acid yield purple adducts which were obtained in small amount compared to the colorless ones. The latter were shown to proceed to more polymerized and yellowish derivatives. Finally, in the case of furfural and HMF purple compounds involving flavanol and anthocyanin units were detected and colorless compounds were shown to be predominant and to yield yellowish xanthylium salts.