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Merck

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:
57-97-6
Molecular Weight:
256.34
UNSPSC Code:
12352200
NACRES:
NA.25
PubChem Substance ID:
24893738
EC Number:
200-359-5
Beilstein/REAXYS Number:
1912135
MDL number:
MFCD00003600

Product Name

7,12-Dimethylbenz[a]anthracene, ≥95%

InChI key

ARSRBNBHOADGJU-UHFFFAOYSA-N

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

SMILES string

Cc1c2ccccc2c(C)c3c1ccc4ccccc34

assay

≥95%

form

powder

mp

122-123 °C (lit.)

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

Quality Level

200

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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.

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.

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Danger

hcodes

H302,H350

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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Certificates of Analysis (COA)

Lot/Batch Number
SLCM4298
SLCM4297
SLCK9094
SLCK9023
SLBZ8280

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A comparison of the anticarcinogenic properties of four red wine polyphenols
Soleas GJ, et al.
Clinical Biochemistry, 35(2), 119-124 (2002)
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
T Ishikawa et al.
Anticancer research, 19(5A), 3749-3752 (2000-01-08)
A two-stage mouse skin carcinogenesis model was used to examine the effects of IP6 on initiation and promotion phases of tumorigenesis. Seven week old ICR female mice were divided into 6 groups, each consisting of 20 animals. Initiation was performed
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)
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)
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Articles

Carcinogenesis and Epigenetics

Cancer research has revealed that the classical model of carcinogenesis, a three step process consisting of initiation, promotion, and progression, is not complete.

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