1-(4-hydroxyphenylazo)-2,6-dihydroxtnaphthalene | 47141-26-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(4-hydroxyphenylazo)-2,6-dihydroxtnaphthalene
• 英文别名: 1-(4-hydroxyphenylazo)-2,6-dihydroxynaphthalene；1-(4-Hydroxyphenylazo)-naphthalene-2,6-diol；1-[(4-hydroxyphenyl)diazenyl]naphthalene-2,6-diol
• CAS: 47141-26-4
• 化学式: C₁₆H₁₂N₂O₃
• 分子量: 280.283
• InChiKey: AKAPJADGYIGRPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  85.4
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-((4-hydroxyphenyl)diazenyl)naphthalen-2-ol 生成 1-(3,4-Dihydroxyphenylazo)-2-naphthol 、 1-(4-hydroxyphenylazo)-2,6-dihydroxtnaphthalene
  参考文献：
  名称：

  Identification of 1-(3,4-Dihydroxyphenylazo)-2-hydroxynaphthalene as the Product of Oxidation of 1-Phenylazo-2-hydroxynaphthalene (Sudan I, Solvent Yellow 14) by Rat Liver Microsomes

  摘要：

  致癌的偶氮染料1-苯基偶氮-2-羟基萘（苏丹I，溶剂黄14）被大鼠肝微粒体氧化为多种含偶氮代谢物。迄今为止未知结构的其中一种产物已被证实与1-(3,4-二羟基苯基偶氮)-2-羟基萘相同。该产物的鉴定完成了微粒体细胞色素P-450对苏丹I氧化的主要产物的模式。

  DOI：

  10.1135/cccc19942727

文献信息

• Cytochrome P-450 from Tulip Bulbs (Tulipa fosteriana L.) Oxidizes an Azo Dye Sudan I (1-Phenylazo-2-hydroxynaphthalene, Solvent Yellow 14) in vitro
  作者：Marie Stiborová、Hana Hansíková

  DOI：10.1135/cccc19961689

  日期：——

  The microsomal fraction from tulip bulbs (Tulipa fosteriana L.) contains cytochrome P-450 enzymes catalyzing the NADPH-dependent oxidation of the xenobiotic substrate, an azo dye Sudan I (1-phenylazo-2-hydroxynaphthalene, Solvent Yellow 14). C-Hydroxy derivatives [1-(4-hydroxyphenylazo)-2-hydroxynaphthalene, 1-phenylazo-2,6-dihydroxynaphthalene, 1-(4-hydroxyphenylazo)-2,6-dihydroxynaphthalene] and the benzenediazonium ion are the products of the Sudan I oxidation. The oxidation of Sudan I has also been assessed in a reconstituted electron-transport chain with the isolated cytochrome P-450, isolated plant NADPH-cytochrome P-450 reductase and phospholipid. The results are discussed from the point of view of the role of cytochromes P-450 in the metabolism of xenobiotics in plants.

  郁金香鳞茎微粒体（Tulipa fosteriana L.）中含有细胞色素P-450酶，可催化异生物底物偶氮染料苏丹I（1-苯基偶氮-2-羟基萘，溶剂黄14）的NADPH依赖性氧化反应。苏丹I氧化产生C-羟基衍生物[1-(4-羟基苯基偶氮)-2-羟基萘、1-苯基偶氮-2,6-二羟基萘、1-(4-羟基苯基偶氮)-2,6-二羟基萘]和苯重氮离子。在隔离的细胞色素P-450、隔离的植物NADPH-细胞色素P-450还原酶和磷脂的重构电子传递链中，也评估了苏丹I的氧化反应。从细胞色素P-450在植物异生物代谢中的作用角度讨论了结果。
• Oxidation of xenobiotics by plant microsomes, a reconstituted cytochrome P450 system and peroxidase: a comparative study
  作者：M Stiborová、H.H Schmeiser、E Frei

  DOI：10.1016/s0031-9422(00)00123-0

  日期：2000.6

  The microsomal fraction from tulip bulbs (Tulipa fosteriana, L.) contains cytochrome P450 (CYP3, EC 1.14.14.1) and peroxidase (EC 1.11.1.7.) enzymes catalyzing the NADPH - and hydrogen peroxide - dependent oxidation of the xenobiotic substrates, N-nitrosodimethylamine (NDMA), Nw-nitrosomethylaniline (NMA), aminopyrine and 1-phenylazo 2-hydroxynaphthalene (Sudan I), respectively. Oxidation of these model xenobiotics has also been assessed in a reconstituted electron-transport chain with a partially purified CYP fraction, phospholipid and isolated tulip NADPH:CYP reductase (EC 1.6.2.4.). Peroxidase isolated from tulip bulbs (isoenzyme C) oxidizes these xenobiotics, too. Values of kinetic parameters (K-m, V-max), requirements for cofactors (NADPH, hydrogen peroxide), the effect of inhibitors and identification of products formed from the xenobiotics by the microsomal fraction, partially purified CYP and peroxidase C were determined. These data were used to estimate the participation of the CYP preparation and peroxidase C in oxidation of two out of the four studied xenobiotics (NMA, Sudan I) in tulip microsomes. Using such detailed study, we found that the CYP-dependent enzyme system is responsible for the oxidation of these xenobiotics in the microsomal fraction of tulip bulbs. The results demonstrate the progress in resolving the role of plant CYP and peroxidase enzymes in oxidation of xenobiotics. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Identification of 1-(3,4-Dihydroxyphenylazo)-2-hydroxynaphthalene as the Product of Oxidation of 1-Phenylazo-2-hydroxynaphthalene (Sudan I, Solvent Yellow 14) by Rat Liver Microsomes
  作者：Marie Stiborová、Befekadu Asfaw、Eva Frei、Heinz H. Schmeiser、Manfred Wiessler

  DOI：10.1135/cccc19942727

  日期：——

  The carcinogenic azo dye 1-phenylazo-2-hydroxynaphthalene (Sudan I, Solvent Yellow 14) is oxidized by rat liver microsomes to a number of azo-containing metabolites. One of the products of hitherto unknown structure has been shown to be identical with 1-(3,4-dihydroxyphenylazo)-2-hydroxynaphthalene. The identification of this product completed the pattern of major products of Sudan I oxidation by microsomal cytochrome P-450.

  致癌的偶氮染料1-苯基偶氮-2-羟基萘（苏丹I，溶剂黄14）被大鼠肝微粒体氧化为多种含偶氮代谢物。迄今为止未知结构的其中一种产物已被证实与1-(3,4-二羟基苯基偶氮)-2-羟基萘相同。该产物的鉴定完成了微粒体细胞色素P-450对苏丹I氧化的主要产物的模式。