42978-43-8

Basic information

• Product Name: 6-acetoxymethylbenzo(a)pyrene
• Synonyms: 6-acetoxymethylbenzo(a)pyrene
• CAS NO: 42978-43-8
• Molecular Formula: C₂₃H₁₆O₂
• Molecular Weight: 324.39
• Mol File: 42978-43-8.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 422.71°C (rough estimate)
• Flash Point: 211.1°C
• Appearance: /
• Density: 1.1073 (rough estimate)
• Vapor Pressure: 3.14E-11mmHg at 25°C
• Refractive Index: 1.5100 (estimate)
• CAS DataBase Reference: 6-acetoxymethylbenzo(a)pyrene(CAS DataBase Reference)
• NIST Chemistry Reference: 6-acetoxymethylbenzo(a)pyrene(42978-43-8)
• EPA Substance Registry System: 6-acetoxymethylbenzo(a)pyrene(42978-43-8)

Safety Data

• Hazardous Substances Data: 42978-43-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C23H16O2/c1-14(24)25-13-21-18-8-3-2-7-17(18)19-11-9-15-5-4-6-16-10-12-20(21)23(19)22(15)16/h2-12H,13H2,1H3

Upstream product

• 2381-39-7 6-Methylbenzopyrene 
• 10581-12-1 tetramethyl ammonium acetate 

Relevant articles and documents

Radical cations of benzo[a]pyrene and 6-substituted derivatives: Reaction with nucleophiles and DNA

1. Oxidation of benzo[a]pyrene (BP) by I2 in the presence of AgClO4 in benzene generates the BP.+ ClO4- · AgI complex. This same method was used to produce radical cations from 6-FBP, 6-ClBP, 6-BrBP and 6-CH3BP. 2. Reaction of the BP,6-FBP,6-ClBP and 6-BrBP radical cation perchlorates with H2O produced BP 1,6-, 3,6- and 6,12- dione, whereas 6-CH3BP.+ClO4- · AgI yielded 6-CH2OHBP. 3. When BP.+ClO4- · AgI and 6-FBP.+ClO4- · AgI were reacted with NaOAc in H2O/CH3CN (9:1), 6-OAcBP was formed, in addition to the quinones. In the case of 6-CIBP.+ClO4- · AgI, a small amount of 1-OAc-6-ClBP and 3-OAc-6-ClBP was formed in, addition to the diones, whereas for 6-BrBP and 6-CH3BP the reaction products were BP diones and 6-CH2OHBP respectively. 4. These results confirm the localization of charge in the BP.+ at C-6, followed by C-1 and C-3. 5. The reaction of BP with NOBF4 in CH2Cl2 produced BP.+ BF4-, radical cation free of complexation with inorganic salts. 6. Reaction of BP.+BF4- with DNA produced the depurinating adducts BP-6-C8Gua, BP-6-C8dGua and BP-6-N7Gua.

One-Electron Oxidation of 6-Substituted Benzopyrenes by Manganic Acetate. A Model for Metabolic Activation

Radical cations of benzopyrene (BP) and 6-substituted derivatives were generated by one-electron oxidation with 2 equiv of Mn(OAc)3*2H2O.Some of the properties of these radical cations were investigated by nucleophilic trapping with acetate ion.BP produced predominantly 6-OAcBP and small amounts of BP 1,6-, 3,6-, and 6,12-dione. 6-FBP yielded 6-OAcBP, a mixture of 1,6-(OAc)2BP and 3,6-(OAc)2BP, and BP diones.In the case of 6-ClBP and 6-BrBP the major products obtained were a mixture of the 1-OAc and 3-OAc derivatives, and BP diones, while substantial starting material remained unreacted. 6-CH3BP afforded mostly 6-OAcCH2BP, a mixture of 1-OAc and 3-OAc derivatives of 6-CH3BP, and a mixture of 1-OAc and 3-OAc derivatives of 6-OAcCH2BP.These results indicate that nucleophilic substitution of BP-radical-cation and 6-FBP-radical-cation occurs exclusively at C-6.For 6-ClBP-radical-cation and 6-BrBP-radical-cation substitution at C-1 and C-3, which are the positions of second highest charge density in their radical cations after C-6, complete successfully for nucleophilic substitution.For 6-CH3BP-radical-cation charge localization at C-6 activates the methyl group rendering it the most reactive toward nucleophilic attack.Competitive acetoxylation of 6-CH3BP-radical-cation also occurs to a minor extent at C-1 and C-3.These mechanistic studies have been useful in clarifying some aspects of the metabolism of BP and its halogeno derivatives by cytochrome P-450 and peroxidases.Furthermore, this chemistry can provide some guidance in understanding the mechanism of tumor initiation by these compounds.