7,12-Dimethylbenz(a)anthracene

7,12-Dimethylbenz[a]anthracene[1]
Names
	Preferred IUPAC name 7,12-Dimethyltetraphene
	Other names 7,12-Dimethylbenzo[a]phenanthrene; 7,12-Dimethylbenzanthracene; 7,12-Dimethyltetraphene; 1,4-Dimethyl-2,3-benzophenanthrene
Identifiers
CAS Number	57-97-6 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:254496 ;
ChEMBL	ChEMBL329673 ;
ChemSpider	5779 ;
ECHA InfoCard	100.000.326
PubChem CID	6001;
UNII	F05B6S0395 ;
CompTox Dashboard (EPA)	DTXSID1020510 ;
	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	256.348 g·mol−1
Melting point	122 to 123 °C (252 to 253 °F; 395 to 396 K)
Hazards
Main hazards	T (Toxic)
R-phrases (outdated)	R45 R22
S-phrases (outdated)	S53 S36/37 S45
NFPA 704 (fire diamond)	0 2 0
	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

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. doi:10.1254/jjp.86.302. Archived from the original on 2010-01-17.
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.

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[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. Archived from the original on 2010-01-17.

[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.