US EPA

5147827 

Technical Report 

New Results In The Detection, Identification And Mutagenic Testing Of Heterocyclic Polycyclic Aromatic Hydrocarbons 

Karcher, W; Nelen, A; Depaus, R; Van Eijk, J; Glaude, P; Jacob, J 

1981 

Chemical Analysis and Biological Fate 

The mutagenicity of polycyclic aromatic hydrocarbon was tested in Salmonella-typhimurium (S-typhimurium) and Escherichia-coli (E-coli). High purity sulfur containing heterocyclic aromatic hydrocarbons were obtained by purification of commercial homocyclic samples. In some cases, the compounds were prepared by synthesis. Purity was assessed by a number of analytical methods before use in mutation assays. Mutagenicity was tested by a classical plate assay using S-typhimurium TA-98 and TA-100 and E-coli PKM-101. Mutagenicity was tested in the absence and presence of mice liver oxygenase fractions. The number of revertants was determined in the presence and absence of nicotinamide-adenine-dinucleotide-phosphate (NADP) and compared with the corresponding mutation frequencies of benzo(a)pyrene (50328) and aflatoxin-B under identical test conditions. For identification of heterocyclic aromatic hydrocarbons in material related to coal tar fractions, commercial samples of chrysene (218019) were analyzed. Four heterocyclic compounds were detected and identified by analytical methods. The major impurities were found to be benzo(b)naphtho(2,1-d)thiophene (239350), benzo(b)naphtho(2,3-d)thiophene (243469), benzo(a)carbazole (239010), and benzo(b)naphtho(2,1-d)furan (239305). None of these compounds was mutagenic in the presence or absence of NADP or liver enzyme fractions. However, benzo(2,3)phenanthro(4,5-bcd)thiophene (248851) exhibited significant mutagenicity in relation to benzo(a)pyrene or aflatoxin-B when tested at a 1 microgram dose. The authors conclude that benzo(2,3)phenanthro(4,5-bcd)thiophene is mutagenic because it has the same ring configuration as benzo(a)pyrene.