1-(2-phenylhydrazinyl)naphthalene-2,6-dione | 115440-09-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(2-phenylhydrazinyl)naphthalene-2,6-dione
• 英文别名: 1-phenylazo-2,6-dihydroxynaphthalene；1-(phenylazo)naphthalene-2,6-diol；6-OH-Sudan I；1-phenylazo-naphthalene-2,6-diol；1-Benzolazo-2.6-dioxy-naphthalin；1-Phenylazo-naphthalin-2,6-diol
• CAS: 115440-09-0
• 化学式: C₁₆H₁₂N₂O₂
• 分子量: 264.283
• InChiKey: JVWRDWIVNBPMRR-ISLYRVAYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.67
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  65.18
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-(2-phenylhydrazinyl)naphthalene-2,6-dione 、 hydrogen trichloro-stannate(II) 生成 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  Kehrmann, Chemische Berichte, 1907, vol. 40, p. 1962

  摘要：

  DOI：
• 作为产物：
  描述：

  2,6-萘二酚 、 苯酚 生成 1-(2-phenylhydrazinyl)naphthalene-2,6-dione
  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。
• 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。
• Kehrmann, Chemische Berichte, 1907, vol. 40, p. 1962
  作者：Kehrmann

  DOI：——

  日期：——