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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:
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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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

Signal Word

Danger

Hazard Statements

Hazard Classifications

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

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

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Certificate of Origin

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