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^Y
3D model (JSmol)	Interactive image
Beilstein Reference	1912135
ChEBI	CHEBI:254496^Y
ChEMBL	ChEMBL329673^Y
ChemSpider	5779^Y
ECHA InfoCard	100.000.326
Gmelin Reference	263937
KEGG	C19488
PubChem CID	6001
RTECS number	CW3850000
UNII	F05B6S0395^Y
UN number	3077
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^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
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
Occupational safety and health (OHS/OSH):
Main hazards	T (Toxic)
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H302, H350
Precautionary statements	P201, P202, P264, P270, P281, P301+P312, P308+P313, P330, P405, P501
NFPA 704 (fire diamond)	2 0 0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is ^YN ?) 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 (3): 302–309. doi:10.1254/jjp.86.302. PMID 11488430.
^ 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 (20): 9304–9311. doi:10.1158/0008-5472.can-05-1015. PMID 16230392.

This page was last edited on 19 August 2023, at 01:51

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References