7,12-Dimethylbenz(a)anthracene
- 7,12- dimethyl-1 ,2- benzanthracene
- 9,10- dimethyl-1 ,2- benzanthracene
- DMBA
Gray - green to yellow
Fixed
123 ° C.
- Practically insoluble in water ( 0.061 mg · l-1, 20 ° C)
- Little in ethanol
- Easily soluble in benzene, toluene and acetone
Risk
Not classified as carcinogenic effect
Template: Infobox chemical / molecular formula search available
7,12- dimethylbenz [a ] anthracene, usually abbreviated with DMBA, a polycyclic aromatic hydrocarbon ( PAH). The base of the compound is benzo [a ] anthracene. DMBA is highly carcinogenic, one of the most potent carcinogens and one of the most carcinogenic polycyclic aromatic hydrocarbons.
It is used in oncology for inducing tumors in model organisms.
Properties
DMBA is greenish- yellow crystals, melting at 122.5 ° C. It is very poorly soluble in water. Only 0.055 mg dissolve in a liter of water at 24 ° C. The octanol - water partition coefficient (log K) is 5.70. DMBA is highly soluble in acetone and in benzene.
Use
Because of its strong carcinogenic effect there is no technical application for DMBA. In oncology there is a commonly used standard carcinogen to form malignant tumors in model organisms.
DMBA is thereby decomposed in the organism of the P450 enzymes to metabolites, which form adducts with DNA.
In model organisms, depending on the form to application skin cancer or breast cancer can be generated. Similarly, leukemia and tumors in other organs can be induced.
Discovery history
DMBA was first synthesized in 1938 by WE Bachmann and JM Chemerda. The carcinogenic potency of DMBA was also discovered by WE Bachmann and colleagues at the University of Michigan in the same year. They have found that DMBA in mice induced tumors twice as fast as 3- methylcholanthrene. In variations on the benz [a ] anthracene - base body they could identify that the 7,12- position of the methylene groups is responsible for a high carcinogenicity.