D3254

Sigma-Aldrich

7,12-Dimethylbenz[a]anthracene

≥95%

Synonym(s):
DMBA, 1,4-Dimethyl-2,3-benzophenanthrene, 9,10-Dimethyl-1,2-benzanthracene
Empirical Formula (Hill Notation):
C20H16
CAS Number:
Molecular Weight:
256.34
Beilstein/REAXYS Number:
1912135
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.25

Quality Level

assay

≥95%

form

powder

mp

122-123 °C (lit.)

SMILES string

Cc1c2ccccc2c(C)c3c1ccc4ccccc34

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

InChI key

ARSRBNBHOADGJU-UHFFFAOYSA-N

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Related Categories

General description

7,12-Dimethylbenz[a]anthracene belongs to the category of polycyclic aromatic hydrocarbons. It is a carcinogenic organic pollutant generated from the incomplete combustion of gasoline and coal.

Application

7,12-Dimethylbenz[a]anthracene was used:
  • to study the effects of Cimicifuga racemosa (CR) extract on the growth of mammary tumor induced by 7,12-Dimethylbenz[a]anthracene
  • in the study to compare the anti-carcinogenic properties of four red wine polyphenols as an initiator to cause skin cancer in CD-1 mouse model
  • to induce epithelial carcinogenicity in order to study the apoptotic, proliferating and p12doc-1 profiles of normal, hyperplastic, dysplastic and malignant oral epithelium in the cheek pouch of the Syrian hamster
  • to cause mammary tumors to examine the causes and prevention of triacylglycerol accumulation in rat liver due to tamoxifen

Packaging

100 mg in glass bottle
1, 5 g in glass bottle

Biochem/physiol Actions

7,12-Dimethylbenz[a]anthracene has been found to be cytotoxic in nature, having carcinogenic properties. It also shows selective necrosis and hemorrhaging in the adrenal gland along with an inhibitory effect on plasma alkaline phosphatase levels. Its damaging effects are due to its ability to form charge transfer complexes by donating electrons to appropriate electron acceptors.

pictograms

Exclamation markHealth hazard

signalword

Danger

hazcat

Acute Tox. 4 Oral - Carc. 1B

storage_class_code

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK Germany

WGK 3

Flash Point F

Not applicable

Flash Point C

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

C HUGGINS et al.
The Journal of experimental medicine, 114, 741-760 (1961-11-01)
Invariably in every normal rat a single dose of 7, 12-dimethylbenz(a)anthracene, by mouth or injected in a vein, was found to cause apoplexy and massive necrosis in the inner zones of the adrenal cortex; the zona glomerulosa, the adrenal medulla...
Sequential expression of inducible nitric oxide synthase and cyclooxygenase-2 during DMBA-induced hamster buccal pouch carcinogenesis
Kim SA, et al.
In Vivo, 18(5), 609-614 (2004)
Yohko Kohno et al.
Oral oncology, 38(3), 274-280 (2002-04-30)
Disruption of the homeostatic balance between proliferation and apoptosis is widely believed to contribute to human oral carcinogenesis. Using the Syrian hamster oral cancer model, we examined normal, hyperplastic, dysplastic and malignant oral epithelium for the fraction of apoptotic, proliferating...
Steroid receptor coactivators, HER-2 and HER-3 expression is stimulated by tamoxifen treatment in DMBA-induced breast cancer
Moi LLH, et al.
BMC Cancer, 12(1), 247-247 (2012)
A comparison of the anticarcinogenic properties of four red wine polyphenols
Soleas GJ, et al.
Clinical Biochemistry, 35(2), 119-124 (2002)
Articles
Cancer research has revealed that the classical model of carcinogenesis, a three step process consisting of initiation, promotion, and progression, is not complete.
Read More
Protocols
US EPA Method 8270 (Appendix IX): GC Analysis of Semivolatiles on Equity®-5 (30 m x 0.25 mm I.D., 0.50 μm)
Read More

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