7,12-Dimethylbenz(a)anthracene

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


IUPAC name 7,12-dimethylbenzo[b]phenanthrene
Identifiers
CAS number	57-97-6^Y
PubChem	6001
ChemSpider	5779^Y
ChEBI	CHEBI:254496^Y
ChEMBL	CHEMBL329673^Y
Jmol-3D images	Image 1
SMILES c32c(c1ccccc1c(c2ccc4c3cccc4)C)C
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^Y Key: ARSRBNBHOADGJU-UHFFFAOYSA-N^Y 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
Properties
Molecular formula	C₂₀H₁₆
Molar mass	256.34104
Melting point	122–123 °C
Hazards
R-phrases	R45 R22
S-phrases	S53 S36/37 S45
Main hazards	T (Toxic)
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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

References

^ 7,12-Dimethylbenz(a)anthracene at Sigma-Aldrich
^ 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. Link
^ 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