6-methoxy-1-nitropyrene | 1732-34-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 6-methoxy-1-nitropyrene
• 英文别名: methyl-(6-nitro-pyren-1-yl)-ether；Methyl-(6-nitro-pyren-1-yl)-aether；6-Nitro-1-methoxy-pyren
• CAS: 1732-34-9
• 化学式: C₁₇H₁₁NO₃
• 分子量: 277.279
• InChiKey: ZLWXDRVSKNMDPW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  52.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  1-甲氧基芘 在 硝酸 、 溶剂黄146 作用下， 生成 6-methoxy-1-nitropyrene 、 methyl-(8-nitro-pyren-1-yl)-ether
  参考文献：
  名称：

  CH216314

  摘要：

  公开号：

文献信息

• Condensation products containing nitrogen and process of making same
  申请人：SOC OF CHEMICAL IND

  公开号：US02189503A1

  公开（公告）日：1940-02-06
• CH216314
  申请人：——

  公开号：——

  公开（公告）日：——
• Sensitive and Selective Detection of Urinary 1-Nitropyrene Metabolites following Administration of a Single Intragastric Dose of Diesel Exhaust Particles (SRM 2975) to Rats
  作者：Yvette M. van Bekkum、Petra H. H. van den Broek、Paul T. J. Scheepers、Rob P. Bos

  DOI：10.1021/tx980162x

  日期：1998.11.1

  1-Nitropyrene (1-NP) has been proposed as a marker for exposure to diesel exhaust particles (DEP). Since the extent of the actual intake of 1-NP adsorbed on DEP will be relatively low, sensitive and selective methods are needed regarding human exposure assessment. Two analytical methods are presented for the assessment of 1-NP metabolites in urine of male Sprague-Dawley rats administered a single intragastric dose of native DEP (SRM 2975, 20 mg, 35.7 mu g of 1-NP/g). Enzymatically hydrolyzed urine was extracted using Blue Rayon. The extracts were analyzed directly, using HPLC with postcolumn on-line reduction and fluorescence detection (HPLC-Flu), or were processed further for GC/MS/MS analysis. Although sensitive to several metabolites, the HPLC-Flu method lacked selectivity for quantitation of some important metabolites in rat urinary extracts, and therefore seems suitable for screening purposes only. With regard to GC/MS/MS analysis, derivatization with heptafluorobutyrylimidazole (HFBI) yielded low limits of determination for hydroxy-l-aminopyrenes, hydroxy-N-acetyl-1-aminopyrenes (converted to derivatized hydroxy-l-aminopyrenes by the reagent), and l-aminopyrene (1.8-9.2 fmol on the column). Derivatization of hydroxy-l-nitropyrenes yielded relatively high limits of determination, and therefore, hydroxy-l-nitropyrenes were reduced to hydroxy-l-aminopyrenes prior to derivatization with HFBI. Intragastric administration of DEP to rats resulted in urinary excretion of 6-hydroxy-N-acetyl-1-aminopyrene, 8-hydroxy-N-acetyl-1-aminopyrene, 6-hydroxy-1-nitropyrene, 8-hydroxy-1-nitropyrene, and 3-hydroxy-1-nitropyrene (7, 1.2, 1.6, 0.3, and 0.5% of the dose within 12 h, respectively), l-Nitropyrene, N-acetyl-1-aminopyrene, and 3-, 6-, and 8-hydroxy-1-aminopyrene were not observed as urinary metabolites following administration of a single dose of DEP. The observed excretion pattern and urinary metabolite concentrations suggest that 1-NP present on unmodified DEP becomes bioavailable to a large extent and is metabolized in the same way as was previously observed following administration of pure 1-NP. The presented methods are promising for assessment of human exposure to 1-NP, e.g., following exposure to DEP, because of the possibility of analyzing large volumes of urine, the conversion of three types of metabolites to one (the amino metabolites), and the low detection limits that are achieved.
• Vollmann et al., Justus Liebigs Annalen der Chemie, 1937, vol. 531, p. 1,38
  作者：Vollmann et al.

  DOI：——

  日期：——