4-amino-5-formyl-pentadienoic acid | 145005-85-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 4-amino-5-formyl-pentadienoic acid
• 英文别名: (2Z,4E)-4-amino-6-oxohexa-2,4-dienoic acid
• CAS: 145005-85-2
• 化学式: C₆H₇NO₃
• 分子量: 141.126
• InChiKey: ZRFQPKHDUMHTEP-REDYYMJGSA-N

物化性质

• 沸点：
  424.4±35.0 °C(Predicted)
• 密度：
  1.280±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  80.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  对氨基苯酚 在 氧气 作用下， 以7 mg的产率得到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

文献信息

• Tyrosinase-catalysed oxidation of the new melanocytotoxic agent N-4-hydroxyphenylglycine: Unusual cleavage of the 4-aminophenol ring to muconic semialdehyde derivatives.
  作者：Donatella Mascagna、Claudio Costantini、Marco d'Ischia、Giuseppe Prota

  DOI：10.1016/s0040-4020(01)80498-1

  日期：1992.1

  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.