2564-65-0

Basic information

• Product Name: 7,12-dihydroxymethylbenz(a)anthracene
• Synonyms: 7,12-dihydroxymethylbenz(a)anthracene;Benz[a]anthracene-7,12-dimethanol
• CAS NO: 2564-65-0
• Molecular Formula: C20H16 O2
• Molecular Weight: 288.36
• Mol File: 2564-65-0.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 390.57°C (rough estimate)
• Flash Point: 283.5°C
• Appearance: /
• Density: 1.0992 (rough estimate)
• Vapor Pressure: 1.17E-14mmHg at 25°C
• Refractive Index: 1.7870 (estimate)
• CAS DataBase Reference: 7,12-dihydroxymethylbenz(a)anthracene(CAS DataBase Reference)
• NIST Chemistry Reference: 7,12-dihydroxymethylbenz(a)anthracene(2564-65-0)
• EPA Substance Registry System: 7,12-dihydroxymethylbenz(a)anthracene(2564-65-0)

Safety Data

• Hazardous Substances Data: 2564-65-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C20H16O2/c21-11-18-15-7-3-4-8-16(15)19(12-22)20-14-6-2-1-5-13(14)9-10-17(18)20/h1-10,21-22H,11-12H2

Upstream product

• 34331-98-1 7,12-bis(bromomethyl)benz[a]anthracene 
• 57-97-6 7,12-dimethyl-1,2-benzanthracene 
• 961-07-9 2'-Deoxyguanosine 
• 63018-62-2 7,12-bis-acetoxymethyl-benz[a]anthracene 

Downstream Products

• 19926-22-8 7.12-Diformyl-benzanthracen 
• 19926-21-7 7-Formyl-12-hydroxy-methyl-benzanthracen 

Relevant articles and documents

Synthesis and structure determination of the adducts of the potent carcinogen 7,12-dimethylbenz[a]anthracene and deoxyribonucleosides formed by electrochemical oxidation: Models for metabolic activation by one-electron oxidation

Anodic oxidation of 7,12-dimethylbenz[a]anthracene (7,12-DMBA) in the presence of dG yields four adducts and one oxygenated derivative of 7,12-DMBA: 7-methylbenz[a]anthracene (MBA)-12-CH2-C8dG (13%), 7-MBA-12-CH2-N7Gua (55%), 12-MBA-7-CH2-N7Gua (12%), 7-MBA-12-CH2-C8Gua (10%), and 7,12-(CH2OH)2-BA (10%). The first three are primary products of the electrochemical reaction, whereas the last two are secondary products. Binding occurs predominantly at the 12-CH3 group of 7,12-DMBA and specifically to the N-7 and C-8 of Gua. On the other hand, anodic oxidation of 7,12-DMBA in the presence of dA gives only two detectable adducts: 7-MBA-12-CH2-N7Ade (45%) and 12-MBA-7-CH2-N3Ade (55%). Binding at the 12-CH3 group is specific for the N-7 of Ade, whereas the 7-CH3 group of 7,12-DMBA is specific for the N-3 of Ade. Structures of the adducts were elucidated by NMR and fast atom bombardment tandem mass spectrometry (FAB MS/MS). The adducts were also investigated by fluorescence line narrowing spectroscopy (FLNS). Both the FAB MS/MS and FLNS techniques can be used to distinguish between the adducts formed at the 7-CH3 and 12-CH3 groups of 7,12-DMBA (i.e., between 7-MBA-12-CH2-N7Gua and 12-MBA-7-CH2-N7Gua and between 7-MBA-12-CH2-N7Gua and 7-MBA-12-CH2-C8Gua). FLNS can distinguish 12-MBA-7-CH2-N3Ade from 7-MBA-12-CH2-N7Ade. On the other hand, the distinction between 7-MBA-12-CH2-C8Gua and 7-MBA-12-CH2-C8dG is straightforward by FAB MS but very difficult by FLNS. The electrochemical synthesis not only provides a demonstration of the specific reactivity of nucleosides and 7,12-DMBA under oxidizing conditions but is also a source of the necessary reference materials for studying the 7,12-DMBA-DNA adducts formed in biological systems. Furthermore, the analytical methodology is now appropriate for supporting in vivo studies of 7,12-DMBA-DNA adducts. A mechanism is proposed, although there are not sufficient data to prove it.