57-97-6 Usage
Description
7,12-DIMETHYLBENZ[A]ANTHRACENE, also known as a tetraphene with methyl substituents at the 7and 12-positions, is a potent carcinogen that is present in tobacco smoke. It appears as yellow to greenish-yellow crystals or a yellow solid, odorless, with maximum fluorescence at 440 nm and exhibits a bluish-violet fluorescence in UV light.
Uses
Used in Pharmaceutical and Toxicological Research:
7,12-DIMETHYLBENZ[A]ANTHRACENE is used as a potent carcinogen for studying the effects of various treatments and substances on tumor growth and carcinogenicity. It is activated by microsomal enzymes to a diol epoxide metabolite that binds covalently to DNA in mammalian cells, leading to tumor induction.
Used in Cancer Studies:
In the study of the effects of Cimicifuga racemosa (CR) extract on the growth of mammary tumors, 7,12-DIMETHYLBENZ[A]ANTHRACENE is used as an initiator to induce mammary tumors in rat liver.
Used in Skin Cancer Research:
7,12-DIMETHYLBENZ[A]ANTHRACENE is used as an initiator to cause skin cancer in CD-1 mouse models, allowing researchers to compare the anti-carcinogenic properties of various substances.
Used in Oral Cancer Research:
7,12-DIMETHYLBENZ[A]ANTHRACENE is used to induce epithelial carcinogenicity in the cheek pouch of the Syrian hamster, enabling the study of apoptotic, proliferating, and p12doc-1 profiles of normal, hyperplastic, dysplastic, and malignant oral epithelium.
Used in Mammary Tumor Studies:
7,12-DIMETHYLBENZ[A]ANTHRACENE is used to cause mammary tumors in order to examine the causes and prevention of triacylglycerol accumulation in rat liver due to tamoxifen treatment.
Used in Chemical Research:
7,12-DIMETHYLBENZ[A]ANTHRACENE, as a yellow powder, is utilized in chemical research to study its properties and potential applications in various fields.
Synthesis Reference(s)
The Journal of Organic Chemistry, 36, p. 966, 1971 DOI: 10.1021/jo00806a023
Air & Water Reactions
Insoluble in water.
Reactivity Profile
7,12-DIMETHYLBENZ[A]ANTHRACENE is incompatible with strong oxidizing agents .
Fire Hazard
7,12-DIMETHYLBENZ[A]ANTHRACENE is combustible.
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.
Safety Profile
Suspected carcinogen
with experimental carcinogenic,
neoplastigenic, tumorigenic, and teratogenic
data. A transplacental carcinogen. Poison by
ingestion, intravenous, subcutaneous,
intraperitoneal, and intratracheal routes.
Other experimental reproductive effects.
Human mutation data reported. A skin
irritant. When heated to decomposition it
emits acrid smoke and irritating fumes.
Purification Methods
Purify DMBA by chromatography on alumina/toluene or *benzene. Crystallise it from acetone/EtOH. [Beilstein 5 IV 2587.]
Check Digit Verification of cas no
The CAS Registry Mumber 57-97-6 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 7 respectively; the second part has 2 digits, 9 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 57-97:
(4*5)+(3*7)+(2*9)+(1*7)=66
66 % 10 = 6
So 57-97-6 is a valid CAS Registry Number.
InChI:InChI=1/C20H16/c1-13-7-8-15-9-10-18-11-16-5-3-4-6-17(16)12-19(18)20(15)14(13)2/h3-12H,1-2H3