5-[(E)-2-carboxyethenyl]-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzofuran-3-carboxylic acid

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: 5-[(E)-2-carboxyethenyl]-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzofuran-3-carboxylic acid
• 化学式: C₁₈H₁₄O₈
• 分子量: 358.304
• InChiKey: ZHLFAYUSKKWDOH-DAFODLJHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  145
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  TRANS-咖啡酸 、 阿魏酸 在 双氧水 、 木榴油 作用下， 以 acetate buffer 为溶剂， 生成 5-[(E)-2-carboxyethenyl]-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzofuran-3-carboxylic acid 、 (4E)-2-(3,4-dihydroxyphenyl)-4-(4-hydroxy-3-methoxybenzylidene)-5-oxotetrahydrofuran-3-carboxylic acid 、 5-[(E)-2-carboxyvinyl]-7-hydroxy-2β-(4-hydroxy-3-methoxyphenyl)-2,3-dihydro-1-benzofuran-3α-carboxylic acid 、 5-[(E)-2-carboxyvinyl]-2-(3,4-dihydroxyphenyl)-7-methoxy-2,3-dihydro-1-benzofuran-3-carboxylic acid
  参考文献：
  名称：

  Modeling suberization with peroxidase-catalyzed polymerization of hydroxycinnamic acids: Cross-coupling and dimerization reactions

  摘要：

  An anionic potato peroxidase (EC 1.11.1.7, APP) thought to be involved in suberization after wounding was isolated from slices of Solanum tuberosum in order to elucidate the first steps of dehydrogenative polymerization between pairs of different hydroxycinnamic acids (FA, CafA, CA and SA) present in wound-healing plant tissues. Use of a commercial horseradish peroxidase (HRP)-H2O2 catalytic system gave the identical major products in these coupling reactions, providing sufficient quantities for purification and structural elucidation. Using an equimolar mixture of pairs of hydroxycinnamic acid suberin precursors, only caffeic acid is coupled to ferulic acid and sinapic acid in separate cross-coupling reactions. For the other systems, HRP and APP reacted as follows: (1) preferentially with ferulic acid in a reaction mixture that contained p-coumaric and ferulic acids; (2) with sinapic acid in a mixture of p-coumaric and sinapic acids; (3) with sinapic acid in a mixture of ferulic and sinapic acids; (4) with caffeic acid in a reaction mixture of p-coumaric and caffeic acids. The resulting products, isolated and identified by NMR and MS analysis, had predominantly beta-beta-gamma-lactone and beta-5 benzofuran molecular frameworks. Five cross-coupling products are described for the first time, whereas the beta-O-4 dehydrodimers identified from the caffeic acid and sinapic acid cross-coupling reaction are known materials that are highly abundant in plants. These reactivity trends lead to testable hypotheses regarding the molecular architecture of intractable suberin protective plant materials, complementing prior analysis of monomeric constituents by GC-MS and polymer functional group identification from solid-state NMR, respectively. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2006.01.026