(+)-Benzo(a)pyrene-7,8-dihydrodiol-9,10-epoxide
Cancer-causing agent derived from tobacco smoke / From Wikipedia, the free encyclopedia
(+)-Benzo[a]pyrene-7,8-dihydrodiol-9,10-epoxide is an organic compound with molecular formula C20H14O3. It is a metabolite and derivative of benzo[a]pyrene (found in tobacco smoke[1]) as a result of oxidation to include hydroxyl and epoxide functionalities. (+)-Benzo[a]pyrene-7,8-dihydrodiol-9,10-epoxide binds to the N2 atom of a guanine nucleobase in DNA,[2][3] distorting the double helix structure[4] by intercalation of the pyrene moiety between base pairs through π-stacking.[5] The carcinogenic properties of tobacco smoking are attributed in part to this compound binding and inactivating the tumor suppression ability of certain genes, leading to genetic mutations and potentially to cancer.[6]
The correct title of this article is (+)-Benzo[a]pyrene-7,8-dihydrodiol-9,10-epoxide. The substitution of any brackets is due to technical restrictions.
Quick Facts Names, Identifiers ...
Names | |
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Preferred IUPAC name
(7R,8S,8aS,9aR)-7,8,8a,9a-Tetrahydrobenzo[1,12]tetrapheno[10,11-b]oxirene-7,8-diol | |
Other names
(+)-Benzo[a]pyrene-7,8-dihydrodiol-9,10-epoxide (+)-7,8,9,10-Tetrahydrobenzo[a]pyrene-7,8-diol-9,10-epoxide (7R,8S,8aR,9aS)-7,8,8a,9a-Tetrahydrobenzo[1,12]tetrapheno[10,11-b]oxirene-7,8-diol 7,8,8a,9a-Tetrahydro-(7R,8S,8aR,9aS)-benzo[10,11]chryseno[3,4-b]oxirene-7,8-diol | |
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Properties | |
C20H14O3 | |
Molar mass | 302.329 g·mol−1 |
Density | 1.6 ± 0.1 g cm−3 |
Boiling point | 594.2 ± 50.0 °C at 760 mmHg |
Dimethyl sulfoxide, dichloromethane, methanol | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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