DIBENZO(A,I)PYRENE

Chemical properties

Yellow Solid

The Uses of DIBENZO(A,I)PYRENE

An active metabolite from inhalation and dermal exposure to polycyclic aromatics hydrocarbons in hot mix asphalt paving workers. DBC is the most potent tumorigen that has been identified to date. Dib enzo[def,p]chrysene (DBC) is a carcinogen and should be handled with appropriate caution.

Definition

ChEBI: Dibenzo[a,l]pyrene is an ortho- and peri-fused polycyclic arene. It has a role as a mutagen and a human metabolite.

General Description

Yellow odorless crystals or flakes. Water insoluble.

Air & Water Reactions

Dust/air mixtures may ignite and explode. Insoluble in water.

Reactivity Profile

Vigorous reactions, sometimes amounting to explosions, can result from the contact between aromatic hydrocarbons, such as DIBENZO(A,I)PYRENE, and strong oxidizing agents. They can react exothermically with bases and with diazo compounds. Substitution at the benzene nucleus occurs by halogenation (acid catalyst), nitration, sulfonation, and the Friedel-Crafts reaction.

Safety Profile

Confirmed carcinogen with experimental tumorigenic data. When heated to decomposition it emits acrid smoke and irritating fumes.

Carcinogenicity

Dibenzo[a,1]pyrene is a class 2B carcinogen according to the IARC, although recent data suggest that it is a 2A carcinogen. In mouse studies, it has been more potent than benzo[a]pyrene in skin, and in rat studies, it has been more potent than 7,12-dimethylbenz [a]anthracene in the mammary gland. Dibenzo[a,l]pyrene was tested for carcinogenicity in studies of single and repeated dermal application to mice, as well as several initiation–promotion studies on mouse skin; all studies gave positive results. Dibenzo[a,l] pyrene also induced oral cavity tumors when applied dermally to the tongue of hamsters and lung tumors in mice following intraperitoneal injection. In addition to lung tumors, dibenzo[a,l]pyrene induced hepatic tumors and a variety of tumors at other sites when administered intraperitoneally to newborn mice. Multiple tumor sites were also observed following intragastric application of dibenzo[a,l]pyrene in mice. Intramamillary administration to rats also yielded positive results. Furthermore, two studies on fish demonstrated that nonmammalian species are also susceptible to dibenzo[a,l]pyreneinduced tumorigenicity.The most active metabolite is the potent 11,12-dihydrodiol of dibenzo[a,1] pyrene.