63041-91-8

Basic information

• Product Name: 7-NITROBENZ[A,H]ANTHRACENE
• Synonyms: 7-NITROBENZ[A,H]ANTHRACENE;Ccris 8424;Dibenz(A,H)anthracene, 7-nitro-
• CAS NO: 63041-91-8
• Molecular Formula: C22H13NO2
• Molecular Weight: 323.34
• Mol File: 63041-91-8.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 578 °C at 760 mmHg
• Flash Point: 284 °C
• Appearance: /
• Density: 1.36 g/cm³
• Vapor Pressure: 9.33E-13mmHg at 25°C
• Refractive Index: 1.827
• CAS DataBase Reference: 7-NITROBENZ[A,H]ANTHRACENE(CAS DataBase Reference)
• NIST Chemistry Reference: 7-NITROBENZ[A,H]ANTHRACENE(63041-91-8)
• EPA Substance Registry System: 7-NITROBENZ[A,H]ANTHRACENE(63041-91-8)

Safety Data

• Hazardous Substances Data: 63041-91-8(Hazardous Substances Data)

Usage

General Description

7-NITROBENZ[A,H]ANTHRACENE is a chemical compound that belongs to the class of polycyclic aromatic hydrocarbons (PAHs) and is known to be a potent carcinogen. It is a yellow crystalline solid and is primarily used in research settings to study the effects of exposure to PAHs on living organisms. 7-NITROBENZ[A,H]ANTHRACENE is mutagenic, causing changes to the genetic material of cells, and has been linked to an increased risk of developing cancer, particularly in the liver and skin. It is also known to be harmful to aquatic life, and its presence in the environment is of concern due to its persistence and potential to bioaccumulate in organisms. Due to its hazardous nature, precautions should be taken when handling and disposing of 7-NITROBENZ[A,H]ANTHRACENE to minimize its impact on human health and the environment.

InChI:InChI=1/C22H13NO2/c24-23(25)22-19-12-11-14-5-1-3-7-17(14)20(19)13-16-10-9-15-6-2-4-8-18(15)21(16)22/h1-13H

Upstream product

• 53-70-3 dibenzo[a,h]anthracene 
• 7697-37-2 nitric acid 
• 64-19-7 acetic acid 

Relevant articles and documents

Structure, tumorigenicity, microsomal metabolism, and DNA binding of 7- nitrodibenz[a,h]anthracene

It has been previously proposed that a nitropolycyclic aromatic hydrocarbon (nitro-PAH) with its nitro functional group perpendicular or nearly perpendicular to the aromatic moiety exhibits lower tumorigenicity than the corresponding parent aromatic hydrocarbon. We also hypothesized that reduction of the nitro group is not involved, or contributed less significantly in the metabolic activation of this class of nitro-PAHs. To verify this hypothesis, we selected 7-nitrodibenz[a,h]anthracene (7- NDB[a,h]A) for study. The X-ray crystallographic structure of 7-NDB[a,h]A was determined and indicated that the dihedral angle between the nitro functional group and the aromatic dibenz[a,h]anthracenyl moiety was 80.6°, indicating the nitro group preferentially adopts a nearly perpendicular orientation. The tumorigenicity of 7-NDB[a,h]A and dibenz[a,h]anthracene (DB[a,h]A) was determined in the male B6C3F1 neonatal mouse. Mice were administered ip injections of 1/7, 2/7, and 4/7 of the total dose of 7-NDB[a,h]A (400 nmol in 35 μL of DMSO per mouse) within 24 h of birth and at 8 and 15 days of age, respectively, and sacrificed at 12 months of age. DB[a,h]A induced 78 and 96% hepatocellular adenomas and carcinomas, respectively. However, 7-NDB[a,h]A induced only 50 and 8% hepatocellular adenomas and carcinomas compared with the 8 and 4% hepatocellular adenomas and carcinomas induced by the solvent vehicle, DMSO. Aerobic metabolism of 7-NDB[a,h]A by liver microsomes of 15- day old male B6C3F1 neonatal mice resulted in trans-3,4-dihydroxy-3,4- dihydro-7-nitrodibenz[a,h]anthracene (7-NDB[a,h]A trans-3,4-dihydrodiol) and trans-10,11-dihydroxy-10,11-dihydro-7-nitrodibenz[a,h]anthracene (7-NDB[a,h]A trans-10,11-dihydrodiol) as predominant metabolites. Under anaerobic conditions, 7-NDB[a,h]A was not metabolized (nitroreduced). The DNA adduct levels in liver and lung tissues of male B6C3F1 mice treated with 7- NDB[a,h]A and sacrificed 24 h and 6 days after final dosing were determined by 32P-postlabeling/TLC. In all cases, the DNA adducts derived from 7- NDB[a,h]A trans-3,4-dihydrodiol and 7-NDB[a,h]A trans-10,11-dihydrodiol were formed. These results suggest that both of the metabolites, 7-NDB[a,h]A trans-3,4-dihydrodiol and 7-NDB[a,h]A trans-10,11-dihydrodiol, are involved in the metabolic activation of 7-NDB[a,h]A, leading to tumor induction in the neonatal mouse. Thus, our results described in this paper support our hypotheses that a nitro-PAH with a perpendicular nitro orientation exhibits lower tumorigenicity than the corresponding parent PAH and that nitroreduction contributes less significantly in the metabolic activation.