(2Z,4E,6E)-4-amino-6-((4-hydroxyphenyl)imino)hexa-2,4-dienoic acid | 145005-84-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (2Z,4E,6E)-4-amino-6-((4-hydroxyphenyl)imino)hexa-2,4-dienoic acid
• CAS: 145005-84-1
• 化学式: C₁₂H₁₂N₂O₃
• 分子量: 232.239
• InChiKey: YIYTXAYOOBXKLQ-BXLLUVLOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.58
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  95.91
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2Z,4E,6E)-4-amino-6-((4-hydroxyphenyl)imino)hexa-2,4-dienoic acid 在 溶剂黄146 作用下， 反应 2.0h， 生成 对氨基苯酚 、 4-amino-5-formyl-pentadienoic acid
  参考文献：
  名称：

  Tyrosinase-catalysed oxidation of the new melanocytotoxic agent N-4-hydroxyphenylglycine: Unusual cleavage of the 4-aminophenol ring to muconic semialdehyde derivatives.

  摘要：

  Oxidation of N-4-hydroxyphenylglycine (1) with tyrosinase in phosphate buffer at pH 6.8 results in two major products, which have been isolated and identified as the novel carboxymethylaminomuconic semialdehyde 3 and the related Schiff base 2. Tyrosinase-catalysed oxidation of 4-aminophenol under similar conditions affords the analogous ring-opened products 6 and 7. Formation of these compounds can be envisaged as proceeding through an unusual cleavage of the 4-aminophenol ring subsequent to its enzymatic conversion to the corresponding o-quinone. Besides disclosing new aspects of the oxidative reactivity of the 4-aminophenol system, the results of this study provide a chemical background to look into the mechanism of the cytotoxic effects of 1 towards human melanoma cells.

  DOI：

  10.1016/s0040-4020(01)80498-1
• 作为产物：
  描述：

  对氨基苯酚 在 氧气 作用下， 反应 2.0h， 生成 (2Z,4E,6E)-4-amino-6-((4-hydroxyphenyl)imino)hexa-2,4-dienoic acid
  参考文献：
  名称：

  Tyrosinase-catalysed oxidation of the new melanocytotoxic agent N-4-hydroxyphenylglycine: Unusual cleavage of the 4-aminophenol ring to muconic semialdehyde derivatives.

  摘要：

  Oxidation of N-4-hydroxyphenylglycine (1) with tyrosinase in phosphate buffer at pH 6.8 results in two major products, which have been isolated and identified as the novel carboxymethylaminomuconic semialdehyde 3 and the related Schiff base 2. Tyrosinase-catalysed oxidation of 4-aminophenol under similar conditions affords the analogous ring-opened products 6 and 7. Formation of these compounds can be envisaged as proceeding through an unusual cleavage of the 4-aminophenol ring subsequent to its enzymatic conversion to the corresponding o-quinone. Besides disclosing new aspects of the oxidative reactivity of the 4-aminophenol system, the results of this study provide a chemical background to look into the mechanism of the cytotoxic effects of 1 towards human melanoma cells.

  DOI：

  10.1016/s0040-4020(01)80498-1