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D3254

Sigma-Aldrich

7,12-Dimethylbenz[a]anthracene

≥95%

Sinonimo/i:

1,4-Dimethyl-2,3-benzophenanthrene, 9,10-Dimethyl-1,2-benzanthracene, DMBA

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About This Item

Formula empirica (notazione di Hill):
C20H16
Numero CAS:
57-97-6
Peso molecolare:
256.34
Beilstein:
1912135
Numero CE:
200-359-5
Numero MDL:
MFCD00003600
Codice UNSPSC:
12352200
ID PubChem:
24893738
NACRES:
NA.25

Saggio

≥95%

Forma fisica

powder

Punto di fusione

122-123 °C (lit.)

applicazioni

metabolomics
vitamins, nutraceuticals, and natural products

Stringa SMILE

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
ARSRBNBHOADGJU-UHFFFAOYSA-N

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Descrizione generale

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.

Applicazioni

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

Azioni biochim/fisiol

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.

Pittogrammi

Health hazardExclamation mark
GHS08,GHS07

Avvertenze

Danger

Indicazioni di pericolo

H302,H350

Classi di pericolo

Acute Tox. 4 Oral - Carc. 1B

Codice della classe di stoccaggio

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

Classe di pericolosità dell'acqua (WGK)

WGK 3

Dispositivi di protezione individuale

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Certificati d'analisi (COA)

Cerca il Certificati d'analisi (COA) digitando il numero di lotto/batch corrispondente. I numeri di lotto o di batch sono stampati sull'etichetta dei prodotti dopo la parola ‘Lotto’ o ‘Batch’.

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Sigma-Aldrich

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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)
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
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Articoli

Carcinogenesis and Epigenetics

Carcinogenesis and Epigenetics

Protocolli

US EPA Method 8270 (Appendix IX): GC Analysis of Semivolatiles on Equity®-5 (30 m x 0.25 mm I.D., 0.50 μm)

US EPA Method 8270 (Appendix IX): GC Analysis of Semivolatiles on Equity®-5 (30 m x 0.25 mm I.D., 0.50 μm)

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