4834-35-9

Basic information

• Product Name: 3-hydroxybenz(a)anthracene
• Synonyms: 3-hydroxybenz(a)anthracene;3-HYDROXYBENZ(A)ANTRHACENE;Benz[a]anthracen-3-ol
• CAS NO: 4834-35-9
• Molecular Formula: C18H12O
• Molecular Weight: 244.2873
• Product Categories: Aromatics, Metabolites & Impurities, Mutagenesis Research Chemicals, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 4834-35-9.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 498.2°Cat760mmHg
• Flash Point: 240.4°C
• Appearance: /
• Density: 1.284g/cm³
• Vapor Pressure: 1.5E-10mmHg at 25°C
• Refractive Index: 1.804
• CAS DataBase Reference: 3-hydroxybenz(a)anthracene(CAS DataBase Reference)
• NIST Chemistry Reference: 3-hydroxybenz(a)anthracene(4834-35-9)
• EPA Substance Registry System: 3-hydroxybenz(a)anthracene(4834-35-9)

Safety Data

• Hazardous Substances Data: 4834-35-9(Hazardous Substances Data)

Usage

Description

3-Hydroxybenz[a]anthracene, also known as Benz[a]anthracen-3-ol, is a chemical compound derived from the potent carcinogenic hydrocarbon, 7,12-Dimethylbenz[a]anthracene (D464500). It is characterized by its ability to be activated by microsomal enzymes into a diol epoxide metabolite, which can bind covalently to DNA in mammalian cells, potentially leading to tumor induction.

Uses

Used in Carcinogenesis Studies:
3-Hydroxybenz[a]anthracene is utilized as a research compound in carcinogenesis studies, particularly focusing on breast cancer. Its role in these studies involves understanding the mechanisms of cancer development and the factors that contribute to tumor induction.
Used in Pharmaceutical Research:
As a derivative of a potent carcinogen, 3-Hydroxybenz[a]anthracene serves as a valuable tool in the development of pharmaceuticals aimed at combating cancer. It can be used to study the interactions between carcinogenic compounds and cellular DNA, which may lead to the discovery of novel therapeutic strategies and the design of more effective chemopreventive agents.
Used in Toxicology and Environmental Studies:
3-Hydroxybenz[a]anthracene is also employed in toxicology and environmental studies to assess the potential health risks associated with exposure to carcinogenic substances. By understanding the effects of this compound on biological systems, researchers can develop better risk assessment models and establish guidelines for safe exposure levels in various environments.

InChI:InChI=1/C18H12O/c19-16-7-8-17-15(10-16)6-5-14-9-12-3-1-2-4-13(12)11-18(14)17/h1-11,19H

Upstream product

• 16434-60-9 1,4,7,12-Tetrahydro-benzanthracen 
• 671780-75-9 3,7,12-trimethoxybenz[a]anthracene 
• 70092-11-4 3-Oxo-1,2,3,4,7,12-tetrahydrobenzanthracen 
• 60967-89-7 (+/-)-trans-3,4-dihydroxy-3,4-dihydrobenzanthracene 
• 69847-25-2 3-methoxybenzanthracene 

Downstream Products

• 74877-25-1 benzanthracene-3,4-dione 
• 60968-10-7 (+/-)-trans-3,4-dihydroxy-1,2,3,4-tetrahydrobenzanthracene 
• 60967-89-7 (+/-)-trans-3,4-dihydroxy-3,4-dihydrobenzanthracene 
• 69847-25-2 3-methoxybenzanthracene 

Relevant articles and documents

Synthesis of the o-Quinones and Other Oxidized Metabolites of Polycyclic Aromatic Hydrocarbons Implicated in Carcinogenesis

Efficient new syntheses of the o-quinone derivatives of benzo[a]pyrene (BPQ), 7,12-dimethylbenz-[a] anthracene (DMBAQ), and benz[a]anthracene (BAQ), implicated as active carcinogenic metabolites of the parent polycyclic aromatic hydrocarbons (PAHs), are reported. These PAH quinones also serve as starting compounds for the synthesis of the other active metabolites of these PAHs thought to be involved in their mechanism(s) of carcinogenesis. The latter include the corresponding o-catechols, trans-dihydrodiols, and the corresponding anti- and syn-diol epoxides.

Tetrabutylammonium Hydroxide: A Reagent for the Base-Catalyzed Dehydration of Vicinal Dihydro Diols of Aromatic Hydrocarbons. Implications to Ion-Pair Chromatography

Vicinal dihydro diols of benzopyrene and benzanthracene are dehydrated to their phenolic derivatives by the methanol eluate of reverse-phase (octadecylsilane) columns previously treated with tetrabutylammonium phosphate.Phenols are also produced by treating the dihydro diols with methanolic tetrabutylammonium hydroxide on removal solvent.In most cases the regioselectivity is markedly different from the acid-catalyzed dehydration.The in situ generated tetrabutylammonium phenoxides are converted to the butyl ethers at high temperatures (150 deg C) but not under th e conditions of dehydration (60 deg C).Tetraethylammonium and tetramethylammonium hydroxides also dehydrate dihydro diols, whereas potassium and sodium hydroxides do not.Dehydration does occur by treatment of dihydro diols with potassium hydroxide in the presence of 1,4,7,10,13,16-hexaoxacyclooctadecane (18-crown-6) and with sodium methoxide in the presence of tetrabutylammonium chloride.A mechanism is suggested.