7,12-Dimethylbenz(a)anthracene

7,12-Dimethylbenz[a]anthracene^[1]

Names
IUPAC name 7,12-Dimethylbenzo[a]phenanthrene
Other names 7,12-Dimethylbenzanthracene; 7,12-Dimethyltetraphene; 1,4-Dimethyl-2,3-benzophenanthrene
Identifiers
CAS Number	57-97-6
ChEBI	CHEBI:254496
ChEMBL	ChEMBL329673
ChemSpider	5779
Jmol interactive 3D	Image
PubChem	6001
InChI InChI=1S/C20H16/c1-13-16-8-5-6-9-17(16)14(2)20-18(13)12-11-15-7-3-4-10-19(15)20/h3-12H,1-2H3 Key: ARSRBNBHOADGJU-UHFFFAOYSA-N InChI=1/C20H16/c1-13-16-8-5-6-9-17(16)14(2)20-18(13)12-11-15-7-3-4-10-19(15)20/h3-12H,1-2H3 Key: ARSRBNBHOADGJU-UHFFFAOYAX
SMILES c32c(c1ccccc1c(c2ccc4c3cccc4)C)C
Properties
Chemical formula	C20H16
Molar mass	256.35 g·mol^−1
Melting point	122 to 123 °C (252 to 253 °F; 395 to 396 K)
Hazards
Main hazards	T (Toxic)
R-phrases	R45 R22
S-phrases	S53 S36/37 S45
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

7,12-Dimethylbenz[a]anthracene (DMBA) is an immunosuppressor and a powerful organ-specific laboratory carcinogen.^[2] DMBA is widely used in many research laboratories studying cancer. DMBA serves as a tumor initiator. Tumor promotion can be induced with treatments of 12-O-tetradecanoylphorbol-13-acetate (TPA) in some models of two-stage carcinogenesis.^[3] This allows for a greatly accelerated rate of tumor growth, making many cancer studies possible.

References

1. 7,12-Dimethylbenz(a)anthracene at Sigma-Aldrich
2. Miyata M, Furukawa M, Takahashi K, Gonzalez FJ, Yamazoe Y (2001). "Mechanism of 7, 12-Dimethylbenz[a]anthracene-Induced Immunotoxicity: Role of Metabolic Activation at the Target Organ". Jpn J Pharmacol 86: 302–309. doi:10.1254/jjp.86.302.
3. Sung YM, He G, Fischer, SM (2005). "Lack of Expression of the EP2 but not EP3 Receptor for Prostaglandin E2 Results in Suppression of Skin Tumor Development". Cancer Res 65: 9304–9311. doi:10.1158/0008-5472.can-05-1015.