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7,12-Dimethylbenz(a)anthracene

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The correct title of this article is 7,12-Dimethylbenz[a]anthracene. The substitution of any brackets is due to technical restrictions.
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
3D model (JSmol)
1912135
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.326 Edit this at Wikidata
263937
KEGG
RTECS number
  • CW3850000
UNII
UN number 3077
  • 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 checkY
    Key: ARSRBNBHOADGJU-UHFFFAOYSA-N checkY
  • 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
  • c32c(c1ccccc1c(c2ccc4c3cccc4)C)C
Properties
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:
GHS07: Exclamation markGHS08: Health hazard
Danger
H302, H350
P201, P202, P264, P270, P281, P301+P312, P308+P313, P330, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 0: Will not burn. E.g. waterInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
0
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

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

[edit]
  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 (3): 302–309. doi:10.1254/jjp.86.302. PMID 11488430.
  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 (20): 9304–9311. doi:10.1158/0008-5472.can-05-1015. PMID 16230392.
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