Synthesis of the carcinogen cyclopenta(c,d)pyrene, its tritiated analog and its proposed active metabolite cyclopenta(c,d)pyrene-3,4-oxide

Conference · Fri Aug 01 00:00:00 EDT 1980 · Am. Chem. Soc., Div. Pet. Chem., Prepr.; (United States)

OSTI ID:7141854

Ruehle, P H; McCaustland, D J; Susan, A C; Wiley, Jr, J C

Cyclopenta(c,d)pyrene 9 (CPP) is a highly mutagenic polyaromatic hydrocarbon (1) of wide environmental distribution. The levels of CPP found in automobile exhaust condensates are 5 to 10 times greater than those of benzo(a)pyrene (2, 3). CPP has also been found in a large variety of carbon soots (4, 5). It has been reported that CPP causes fibrosarcomas in mice (6). The presence in the environment of a carcinogen with a non-bay region structure has stimulated interest in both the parent hydrocarbon (7 to 11) and its proposed ultimate mutagenic intermediate, cyclopenta-(c,d)pyrene-3,4-oxide (12, 13). In the following paper, we present improvements in the synthesis of CPP, a synthesis of its tritiated analog (14) and of its proposed metabolite CPP-3,4-oxide.

• Research Organization: Midwest Research Inst., Kansas City, MO
• OSTI ID: 7141854
• Report Number(s): CONF-800814-P1
• Journal Information: Am. Chem. Soc., Div. Pet. Chem., Prepr.; (United States), Journal Name: Am. Chem. Soc., Div. Pet. Chem., Prepr.; (United States) Vol. 25:3; ISSN ACPCA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
38 RADIATION CHEMISTRY, RADIOCHEMISTRY, AND NUCLEAR CHEMISTRY
400301* -- Organic Chemistry-- Chemical & Physicochemical Properties-- (-1987)
400702 -- Radiochemistry & Nuclear Chemistry-- Properties of Radioactive Materials
AROMATICS
CHEMICAL PREPARATION
EPOXIDES
HYDROCARBONS
LABELLED COMPOUNDS
LABELLING
ORGANIC COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
POLYCYCLIC AROMATIC HYDROCARBONS
SYNTHESIS
TRITIUM COMPOUNDS