7,12-DIMETHYLBENZ[A]ANTHRACENE

DBA is a greenish-yellow solid. Polynucleararomatic hydrocarbons (PAHs) are compounds containingmultiple benzene rings and are also called polycyclic aromatic hydrocarbons. Molecular weight= 256.36; Freezing/Melting point= 122℃. Insoluble in water

Yellow Powder

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 p12^doc-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

A highly potent carcinogen that is activated by microsomal enzymes to a diol epoxide metabolite that binds covalently to DNA in mammalian cells, leading ultimately to tumor induction

ChEBI: A tetraphene having methyl substituents at the 7- and 12-positions. It is a potent carcinogen and is present in tobacco smoke.

The Journal of Organic Chemistry, 36, p. 966, 1971 DOI: 10.1021/jo00806a023

Yellow to greenish-yellow crystals or a yellow solid. Odorless. Maximum fluorescence at 440 nm. Bluish-violet fluorescence in UV light.

Insoluble in water.

7,12-DIMETHYLBENZ[A]ANTHRACENE is incompatible with strong oxidizing agents .

7,12-DIMETHYLBENZ[A]ANTHRACENE is combustible.

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.

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.

Oxidizing agents

If this chemical gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least15 min, occasionally lifting upper and lower lids. If thischemical contacts the skin, remove contaminated clothingand wash immediately with soap and water. If this chemicalhas been inhaled, remove from exposure, begin rescuebreathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if heart actionhas stopped. Transfer promptly to a medical facility

Color Code—Blue: Health Hazard/Poison: Storein a secure poison location. Prior to working with DBA youshould be trained on its proper handling and storage. Storein tightly closed containers in a cool, well-ventilated areaaway from oxidizers. A regulated, marked area should beestablished where this chemical is handled, used, or storedin compliance with OSHA Standard 1910.1045.

The name of this material is not in the DOT listof materials for label and packaging standards. However,based on regulations, it may be classified as anEnvironmentally hazardous substances, solid, n.o.s. Thischemical requires a shipping label of “CLASS 9.” It falls inHazard Class 9 and Packing Group III.[20,21

Purify DMBA by chromatography on alumina/toluene or *benzene. Crystallise it from acetone/EtOH. [Beilstein 5 IV 2587.]

Contact can irritate and burn theskin and eyes. Irritates the respiratory tract. High exposuremay damage the blood cells, causing anemia

The IRSL and SRSL were derived from the inhalation unit risk (IUR) factor for B(a)P of 1.76E-3 per μg/m3 .

[1] THAMARAISELVAN RENGARAJAN . Exposure to polycyclic aromatic hydrocarbons with special focus on cancer[J]. Asian Pacific journal of tropical biomedicine, 2015, 5 3: Pages 182-189. DOI: 10.1016/s2221-1691(15)30003-4
[2] ANNA CSISZAR. Chemically induced carcinogenesis in rodent models of aging: assessing organismal resilience to genotoxic stressors in geroscience research.[J]. GeroScience, 2019, 41 2: 209-227. DOI: 10.1007/s11357-019-00064-4
[3] E HUBERMAN  S K Y  M W Chou. Identification of 7,12-dimethylbenz[a]anthracene metabolites that lead to mutagenesis in mammalian cells.[J]. Proceedings of the National Academy of Sciences of the United States of America, 1979, 76 2: 862-866. DOI: 10.1073/pnas.76.2.862
[4] YEO-JUNG KWON. 7,12-Dimethylbenz[α]anthracene increases cell proliferation and invasion through induction of Wnt/β-catenin signaling and EMT process[J]. Environmental Toxicology, 2018, 33 7: 729-742. DOI: 10.1002/tox.22560
[5] JUN GAO. Cytochrome P450 1B1 is required for 7,12-dimethylbenz(a)-anthracene (DMBA) induced spleen cell immunotoxicity.[J]. Toxicological Sciences, 2005, 86 1: 68-74. DOI: 10.1093/toxsci/kfi176
[6] ALFREDO CARLOS S D BARROS. Induction of experimental mammary carcinogenesis in rats with 7,12-dimethylbenz(a)anthracene.[J]. Revista do Hospital das Clinicas, 2004, 59 5: 257-261. DOI: 10.1590/s0041-87812004000500006
[7] MARIA VÄHÄTUPA. Chemical-Induced Skin Carcinogenesis Model Using Dimethylbenz[a]Anthracene and 12-O-Tetradecanoyl Phorbol-13-Acetate (DMBA-TPA).[J]. Jove-Journal of Visualized Experiments, 2019. DOI: 10.3791/60445