8-O-4'-diferulic acid | 215872-63-2

• 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: 8-O-4'-diferulic acid
• 英文别名: 2-[4-(2-Carboxyethenyl)-2-methoxyphenoxy]-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid；2-[4-(2-carboxyethenyl)-2-methoxyphenoxy]-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid
• CAS: 215872-63-2
• 化学式: C₂₀H₁₈O₈
• 分子量: 386.358
• InChiKey: GGCXWTMEZZGUFT-UHFFFAOYSA-N

物化性质

• 沸点：
  635.1±55.0 °C(Predicted)
• 密度：
  1.403±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  123
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  阿魏酸 在 双氧水 作用下， 以 水 、 丙酮 为溶剂， 生成 8-O-4'-diferulic acid 、 8-5-cyclic dehydrodiferulic acid
  参考文献：
  名称：

  Determination of free diferulic, disinapic and dicoumaric acids in plants and foods

  摘要：

  Hydroxycinnamates are common phenolic compounds of plants and plant foods, often found in substantial quantities. Due to their high in vitro antioxidant activity they can easily be oxidized under oxidative conditions. In this study, we found that in vitro oxidation of coumaric, ferulic and sinapic acids resulted mainly in dimeric compounds. We hypothesized that these dimers are present in plants and plant foods not only in their bound form but also as free acids that can be extracted from non-hydrolyzed samples. By applying sensitive UHPLC-MSIMS method, we were able to identify and quantify four free hydroxycinnamic acid dimers for the first time, namely 8-8'-disinapic, 8-5'-diferulic, 8-O-4'-diferulic and 8-3'-dicoumaric acids, in wheat sprouts, Chinese cabbage, millet sprouts, light beer and parsley. Concentrations of dicinnamates in plant tissues ranged from 0.05 to 2.8 mu g g(-1) DW and the monomer:dimer ratio ranged from 2 to 850. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.foodchem.2014.08.131

文献信息

• Determination of free diferulic, disinapic and dicoumaric acids in plants and foods
  作者：Jiří Grúz、Jiří Pospíšil、Hana Kozubíková、Tomáš Pospíšil、Karel Doležal、Mirko Bunzel、Miroslav Strnad

  DOI：10.1016/j.foodchem.2014.08.131

  日期：2015.3

  Hydroxycinnamates are common phenolic compounds of plants and plant foods, often found in substantial quantities. Due to their high in vitro antioxidant activity they can easily be oxidized under oxidative conditions. In this study, we found that in vitro oxidation of coumaric, ferulic and sinapic acids resulted mainly in dimeric compounds. We hypothesized that these dimers are present in plants and plant foods not only in their bound form but also as free acids that can be extracted from non-hydrolyzed samples. By applying sensitive UHPLC-MSIMS method, we were able to identify and quantify four free hydroxycinnamic acid dimers for the first time, namely 8-8'-disinapic, 8-5'-diferulic, 8-O-4'-diferulic and 8-3'-dicoumaric acids, in wheat sprouts, Chinese cabbage, millet sprouts, light beer and parsley. Concentrations of dicinnamates in plant tissues ranged from 0.05 to 2.8 mu g g(-1) DW and the monomer:dimer ratio ranged from 2 to 850. (C) 2014 Elsevier Ltd. All rights reserved.
• 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.