D3254
7,12-Dimethylbenz[a]anthracene
≥95%
Synonym(s):
1,4-Dimethyl-2,3-benzophenanthrene, 9,10-Dimethyl-1,2-benzanthracene, DMBA
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About This Item
Empirical Formula (Hill Notation):
C20H16
CAS Number:
Molecular Weight:
256.34
UNSPSC Code:
12352200
NACRES:
NA.25
PubChem Substance ID:
EC Number:
200-359-5
Beilstein/REAXYS Number:
1912135
MDL number:
assay
≥95%
form
powder
mp
122-123 °C (lit.)
application(s)
metabolomics
vitamins, nutraceuticals, and natural products
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
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
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.
signalword
Danger
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Carc. 1B
Storage Class
6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
wgk
WGK 3
ppe
Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
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Related Content
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
DMBA acts on cumulus cells to desynchronize nuclear and cytoplasmic maturation of pig oocytes
Song ZQ, et al.
Scientific reports, 7(1), 1687-1687 (2017)
Regio-and stereoselective metabolism of 7, 12-dimethylbenz [a] anthracene by Mycobacterium vanbaalenii PYR-1
Moody JD, et al.
Applied and Environmental Microbiology, 69(7), 3924-3931 (2003)