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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:
1912135
EC Number:
200-359-5
MDL number:
MFCD00003600
UNSPSC Code:
12352200
PubChem Substance ID:
24893738
NACRES:
NA.25
Pricing and availability is not currently available.

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

Signal Word

Danger

Hazard Statements

H302,H350

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SLCM4298
SLCM4297
SLCK9094
SLCK9023
SLBZ8280

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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
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)
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. How is shipping temperature determined? And how is it related to the product storage temperature?

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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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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      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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