2-(4-(2-carboxyvinyl)-2-methoxyphenoxy)-3-(3,4-dihydroxyphenyl)acrylic acid | 1138328-98-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(4-(2-carboxyvinyl)-2-methoxyphenoxy)-3-(3,4-dihydroxyphenyl)acrylic acid
• CAS: 1138328-98-9
• 化学式: C₁₉H₁₆O₈
• 分子量: 372.331
• InChiKey: RCJLRMWWKKUAOO-UHFFFAOYSA-N

物化性质

• 沸点：
  666.3±55.0 °C(predicted)
• 密度：
  1.491±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.71
• 重原子数：
  27.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  133.52
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  8-O-4'-diferulic acid 在 葡萄糖 作用下， 以 二甲基亚砜 为溶剂， 反应 58.0h， 生成 2-(4-(2-carboxyvinyl)-2-methoxyphenoxy)-3-(3,4-dihydroxyphenyl)acrylic acid
  参考文献：
  名称：

  Conversion of Dehydrodiferulic Acids by Human Intestinal Microbiota

  摘要：

  Plant cell wall associated dehydrodiferulic acids (DFA) are abundant components of cereal insoluble dietary fibers ingested by humans. The ability of human intestinal microbiota to convert DFA was studied in vitro by incubating 8-O-4- and 5-5-coupled DFA with fecal suspensions. 8-O-4-DFA was completely degraded by the intestinal microbiota of the majority of donors, yielding homovanillic acid, 3-(3,4-dihydroxyphenyl)propionic acid, and 3,4-dihydroxyphenylacetic acid as the main metabolites. The transient formation of ferulic acid and presumably 3-(3-hydroxy-4-methoxyphenyl)pyruvic acid suggests an initial cleavage of the ether bond. In contrast to 8-O-4-DFA, the 5-5-coupled DFA was not cleaved into monomers by any of the fecal suspensions. Only the side chains were hydrogenated and the methoxy groups were demethylated. The cleavage of DFA by human intestinal microbiota, which depended on their coupling type, may affect both the bioavailability of DFA and the degradability of DFA-coupled fiber in the gut.

  DOI：

  10.1021/jf900159h

文献信息

• Conversion of Dehydrodiferulic Acids by Human Intestinal Microbiota
  作者：Annett Braune、Mirko Bunzel、Reiko Yonekura、Michael Blaut

  DOI：10.1021/jf900159h

  日期：2009.4.22

  Plant cell wall associated dehydrodiferulic acids (DFA) are abundant components of cereal insoluble dietary fibers ingested by humans. The ability of human intestinal microbiota to convert DFA was studied in vitro by incubating 8-O-4- and 5-5-coupled DFA with fecal suspensions. 8-O-4-DFA was completely degraded by the intestinal microbiota of the majority of donors, yielding homovanillic acid, 3-(3,4-dihydroxyphenyl)propionic acid, and 3,4-dihydroxyphenylacetic acid as the main metabolites. The transient formation of ferulic acid and presumably 3-(3-hydroxy-4-methoxyphenyl)pyruvic acid suggests an initial cleavage of the ether bond. In contrast to 8-O-4-DFA, the 5-5-coupled DFA was not cleaved into monomers by any of the fecal suspensions. Only the side chains were hydrogenated and the methoxy groups were demethylated. The cleavage of DFA by human intestinal microbiota, which depended on their coupling type, may affect both the bioavailability of DFA and the degradability of DFA-coupled fiber in the gut.