(+)-Benzo(a)pyrene-7,8-dihydrodiol-9,10-epoxide

(+)-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) 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, distorting the double helix structure by intercalation of the pyrene moiety between base pairs through π-stacking. 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.

(+)-Benzo[a]pyrene-7,8-dihydrodiol-9,10-epoxide
Names
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
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C20H14O3/c21-17-13-8-11-5-4-9-2-1-3-10-6-7-12(15(11)14(9)10)16(13)19-20(23-19)18(17)22/h1-8,17-22H/t17-,18+,19+,20-/m1/s1
    Key: DQEPMTIXHXSFOR-FUMNGEBKSA-N
SMILES
  • O[C@@H]3c1cc4ccc5cccc6ccc(c1[C@H]2O[C@H]2[C@H]3O)c4c56
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).
Infobox references
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