Dibenzoylmethane


Dibenzoylmethane is an organic compound with the formula 2CH2. DBM is the name for a 1,3-diketone, but the compound exists primarily as one of two equivalent enol tautomers. DBM is a white solid. Due to their high photostability and UV-absorbing properties, derivatives of DBM such as avobenzone, have found applications as sunscreen products.

Synthesis and reactions

DBM is prepared by condensation of ethyl benzoate with acetophenone.
Like other 1,3-diketones, DBM condenses with a variety of bifunctional reagents to give heterocycles. Hydrazine gives diphenylpyrazole. Urea and thiourea also condense to give six-membered rings. With metal salts, the conjugate base of DBM forms complexes akin to the metal acetylacetonates.

Occurrence and medicinal properties

Dibenzoylmethane is a minor constituent in the root extract of Licorice. It is also found in Curcumin. These occurrences have led to investigations into the medicinal properties of this class of compounds.
DBM slow disease progression by preventing the cessation of protein synthesis in neurons.

Related compounds