Dibenzoylmethane (DBM) is an organic compound with the formula (C6H5C(O))2CH2. DBM is the name for a 1,3-diketone, but the compound exists primarily as the enol tautomer. The interconversion between the diketone and the two equivalent enols is so rapid that the distinction is usually ignored. DBM (actually its enol) is a white solid. Due to their high photostability, derivatives of DBM such as avobenzone, have found applications as sunscreen products.
3D model (JSmol)
CompTox Dashboard (EPA)
|Molar mass||224.25 g/mol|
|Density||1.334 g cm�3|
|Melting point||77 to 78 °C (171 to 172 °F; 350 to 351 K)|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Synthesis, structure, and reactionsEdit
DBM always crystallizes as the enol.
Like other 1,3-diketones (or their enols), 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.
Dibenzoylmethane (DBM) is a natural phytochemical found as a minor constituent in the root extract of Licorice (Glycyrrhiza glabra in the family Leguminosae). DBM has been shown to prevent the formation of DNA-adducts induced by carcinogens in both in vitro and in vivo studies. DBM induce apoptosis in human prostate and colon cancer cells, and induce cycle arrest in prostate cancer cells.
An investigational use in the treatment of neurodegenerative diseases has been suggested; in the study DBM (and Trazodone) demonstrated potential in slowing disease progression, by preventing the cessation of protein synthesis in neurons.
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