2,3,4-tri-O-acetyl-1-feruloyl-D-glucuronic acid methyl ester | 1414838-04-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 2,3,4-tri-O-acetyl-1-feruloyl-D-glucuronic acid methyl ester
• CAS: 1414838-04-2
• 化学式: C₂₃H₂₆O₁₃
• 分子量: 510.452
• InChiKey: GZXKKMRGOFIVLG-YKZCJQPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.65
• 重原子数：
  36.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  170.19
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-acetyl-1-feruloyl-D-glucuronic acid methyl ester 在 水 、 potassium hydroxide 作用下， 反应 0.67h， 生成 ferulic acid acyl glucuronide
  参考文献：
  名称：

  Antioxidant Activity of Phenolic Acids and Their Metabolites: Synthesis and Antioxidant Properties of the Sulfate Derivatives of Ferulic and Caffeic Acids and of the Acyl Glucuronide of Ferulic Acid

  摘要：

  The main metabolites of caffeic and ferulic acids (ferulic acid-4'-O-sulfate, caffeic acid-4'-O-sulfate, and caffeic acid-3'-O-sulfate), the most representative phenolic acids in fruits and vegetables, and the acyl glucuronide of ferulic acid were synthesized, purified, and tested for their antioxidant activity in comparison with those of their parent compounds and other related phenolics. Both the ferric reducing antioxidant power (FRAP) assay and the 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) radical scavenging method were used. Ferulic acid-4'-O-sulfate and ferulic acid-4'-O-glucuronide exhibited very low antioxidant activity, while the monosulfate derivatives of caffeic acid were 4-fold less efficient as the antioxidant than caffeic acid. The acyl glucuronide of ferulic acid showed strong antioxidant action. The antioxidant activity of caffeic acid-3'-O-glucuronide and caffeic acid-4'-O-glucuronide was also studied. Our results demonstrate that some of the products of phenolic acid metabolism still retain strong antioxidant properties. Moreover, we first demonstrate the ex vivo synthesis of the acyl glucuronide of ferulic acid by mouse liver microsomes, in addition to the phenyl glucuronide.

  DOI：

  10.1021/jf304076z
• 作为产物：
  描述：

  2,3,4-tri-O-acetyl-1-bromo-1-deoxy-β-D-glucopyranuronic acid methy ester 、 阿魏酸 在 sodium hydroxide 作用下， 以 水 、 乙腈 为溶剂， 反应 4.0h， 生成 2,3,4-tri-O-acetyl-1-feruloyl-D-glucuronic acid methyl ester
  参考文献：
  名称：

  Antioxidant Activity of Phenolic Acids and Their Metabolites: Synthesis and Antioxidant Properties of the Sulfate Derivatives of Ferulic and Caffeic Acids and of the Acyl Glucuronide of Ferulic Acid

  摘要：

  The main metabolites of caffeic and ferulic acids (ferulic acid-4'-O-sulfate, caffeic acid-4'-O-sulfate, and caffeic acid-3'-O-sulfate), the most representative phenolic acids in fruits and vegetables, and the acyl glucuronide of ferulic acid were synthesized, purified, and tested for their antioxidant activity in comparison with those of their parent compounds and other related phenolics. Both the ferric reducing antioxidant power (FRAP) assay and the 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) radical scavenging method were used. Ferulic acid-4'-O-sulfate and ferulic acid-4'-O-glucuronide exhibited very low antioxidant activity, while the monosulfate derivatives of caffeic acid were 4-fold less efficient as the antioxidant than caffeic acid. The acyl glucuronide of ferulic acid showed strong antioxidant action. The antioxidant activity of caffeic acid-3'-O-glucuronide and caffeic acid-4'-O-glucuronide was also studied. Our results demonstrate that some of the products of phenolic acid metabolism still retain strong antioxidant properties. Moreover, we first demonstrate the ex vivo synthesis of the acyl glucuronide of ferulic acid by mouse liver microsomes, in addition to the phenyl glucuronide.

  DOI：

  10.1021/jf304076z