1-硝基芘-8-醇 | 1732-29-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 中文名称: 1-硝基芘-8-醇
• 英文名称: 1-hydroxy-8-nitropyrene
• 英文别名: 8-hydroxy-1-nitropyrene；1-nitropyrene-8-ol；1-Nitropyren-8-ol；8-nitropyren-1-ol
• CAS: 1732-29-2
• 化学式: C₁₆H₉NO₃
• 分子量: 263.252
• InChiKey: RHXGKMNLLUKFLG-UHFFFAOYSA-N

物化性质

• 熔点：
  >154°C (dec.)
• 沸点：
  509.7±25.0 °C(Predicted)
• 密度：
  1.528±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  3

ADMET

代谢

8-羟基-1-硝基芘是1-硝基芘的人类已知代谢物。

8-hydroxy-1-nitropyrene is a known human metabolite of 1-nitropyrene.

来源:NORMAN Suspect List Exchange

安全信息

• 海关编码：
  2907199090

反应信息

• 作为反应物：
  描述：

  1-硝基芘-8-醇 在 氯化铵 、 锌 作用下， 以 乙醇 为溶剂， 生成 8-Amino-pyren-1-ol
  参考文献：
  名称：

  Role of O-acetyltransferase in activation of oxidised metabolites of the genotoxic environmental pollutant 1-nitropyrene

  摘要：

  The genotoxic environmental contaminant l-nitropyrene is metabolised in mammalian systems by pathways more complex than the straightforward nitroreduction which accounts for most of its biological activity in bacteria. In order to evaluate the role of O-acetyltransferase (OAT) activity in generation of genotoxic intermediates from 1-nitropyrene, the mutagenicity of the major primary oxidised metabolites of 1-nitropyrene was characterised in the Ames Salmonella typhimurium plate incorporation assay with strain TA98, and with variants of TA98 deficient (TA98/1,8-DNP6) or enhanced (YG1024) in O-acetyltransferase. 1-Nitropyren-3-ol was more mutagenic in the absence than in the presence of S9, while 1-nitropyren-4-ol, 1-nitropyren-6-ol and 1-nitropyren-8-ol required S9 for maximum expression of mutagenicity. 1-Nitropyren-4-ol (176 rev/nmol without S9, 467 rev/nmol with S9 in TA98) and 1-nitropyren-6-ol (13 rev/nmol without S9, 266 rev/nmol with S9 in TA98) were overall the most potent nitropyrenol isomers assayed. 1-Acetamidopyren-8-ol and 2-acetamidopyrene 4,5-quinone were only minimally active. 1-Acetamidopyren-3-ol exhibited direct-acting mutagenicity. 1-Acetamidopyren-6-ol, previously shown to be a major contributor to mutagenicity in the urines of rats dosed with l-nitropyrene (Ball et al., 1984b), was confirmed as a potent (359 rev/nmol) S9-dependent mutagen. Both the direct-acting and the S9-dependent mutagenicity of all the compounds studied was enhanced in the OAT-overproducing strain and much diminished (though not always entirely lost) in the OAT-deficient strain, showing that OAT amplifies expression of the genotoxicity of these compounds. 1-Acetamidopyren-6-ol required both 89 and OAT activity in order to exhibit any mutagenicity; this finding strongly implicates N-hydroxylation followed by O-esterification, as opposed to further S9-catalyzed ring oxidation, as a major route of activation for urinary metabolites of 1-nitropyrene.

  DOI：

  10.1016/s0165-1218(96)90026-9
• 作为产物：
  描述：

  1,8-二硝基芘 在 二环己烷并-18-冠醚-6 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 以98%的产率得到1-硝基芘-8-醇
  参考文献：
  名称：

  硝化多环芳烃的化学氧化：与超氧阴离子自由基羟基化。

  摘要：

  硝化的多环芳烃（nitroPAH）是一种强力的诱变剂，可以通过还原和/或氧化方式代谢。硝基PAH的生物氧化（例如羟基化和环氧化）是已知的，但是仅在几篇论文中报道了化学氧化。由于具有硝基取代基的芳环的电子不足特性，NitroPAH几乎不会被各种化学氧化剂氧化。超氧阴离子自由基的亲核反应性是已知的，因此本研究中进行了硝基PAH与化学生成的超氧阴离子自由基的氧化。当1-硝基py与KO2 / 18-crown-6在二甲基甲酰胺中反应时，可以制备产率得到5-，6-，8-和9-羟基-1-硝基py和1-羟基py。三个异构体二硝基nitro，3-硝基荧蒽，6-硝基苯并[a] py，和6-硝基铬被氧化为羟基衍生物，其中一些对应于硝基PAH的氧化代谢产物。用三氟过氧乙酸将二硝基吡啶氧化，得到K区氧化产物。

  DOI：

  10.1021/tx00043a003

文献信息

• Photodegradation Mechanisms of 1-Nitropyrene, an Environmental Pollutant: The Effect of Organic Solvents, Water, Oxygen, Phenols, and Polycyclic Aromatics on the Destruction and Product Yields
  作者：Zulma I. García-Berríos、Rafael Arce

  DOI：10.1021/jp2126416

  日期：2012.4.12

  ϕ(-1-NO2Py), was larger in toluene, benzene, and polar protic solvents (10–3) in comparison with nonpolar and polar aprotic solvents, where the yield is on the order of 10–4. In solvents with an abstractable hydrogen atom, the products formed in higher yields were 1-OHPy and 1-OH-x-NO2Py. These represent 60–80% of the photodestruction yield and result from abstraction and recombination reactions of the pyrenoxy

  这项工作描述了在由有机溶剂和气溶胶颗粒的已知成分组成的化学模型系统中对 1-硝基芘 (1-NO 2 Py) 的光降解机制的研究。光产物如 1-羟基芘 (1-OHPy)、1-羟基- x -硝基芘 (1-OH- x -NO 2 Py)、1-亚硝基芘以及 1,6- 和 1,8-芘二酮通过高-高效液相色谱（HPLC）和高效液相色谱/质谱（HPLC/MS）技术，其量子产率显示出对溶剂类型的显着依赖性。与非极性和极性非质子溶剂相比，1-NO 2 Py 的光降解量子产率在甲苯、苯和极性质子溶剂 (10 –3 ) 中更大，其中产率在10 – 4的顺序。在具有可提取氢原子的溶剂中，以较高收率形成的产物是1-OHPy和1-OH- x -NO 2 Py。这些代表了 60-80% 的光破坏产率，是芘氧基自由基的提取和重组反应的结果，芘氧基自由基是硝基芳族化合物中硝基-亚硝酸盐重排的中间产物。 O 2对光降解产率的
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