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D3254

Sigma-Aldrich

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

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

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General description

7,12-Dimethylbenz[a]anthracene belongs to the category of polycyclic aromatic hydrocarbons.[1] It is a carcinogenic organic pollutant generated from the incomplete combustion of gasoline and coal.[2]

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[3]
  • 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[4]
  • 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[5]
  • to cause mammary tumors to examine the causes and prevention of triacylglycerol accumulation in rat liver due to tamoxifen[6]

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.[5][1]

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_germany

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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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
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
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)
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)
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)
View All Related Papers

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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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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