Dibenzoylmethane
Chemical compound
From Wikipedia, the free encyclopedia
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 one of two equivalent enol tautomers.[2] DBM is a white solid. Due UV-absorbing properties, derivatives of DBM such as avobenzone, have found applications as sunscreen products.[3]
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| Names | |
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| Preferred IUPAC name
1,3-Diphenylpropane-1,3-dione | |
| Other names
2-Benzoylacetophenone | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
| ECHA InfoCard | 100.003.999 |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C15H12O2 | |
| Molar mass | 224.25 g/mol |
| Appearance | white solid |
| Density | 1.334 g/cm3 |
| Melting point | 77 to 78 °C (171 to 172 °F; 350 to 351 K)[1] |
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 and reactions
DBM is prepared by condensation of ethyl benzoate with acetophenone.[4]
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.[citation needed]
Occurrence and medicinal properties
Dibenzoylmethane (DBM) is a minor constituent in the root extract of Licorice (Glycyrrhiza glabra in the family Leguminosae).[5] It is also found in Curcumin. These occurrences have led to investigations into the medicinal properties of this class of compounds.[6][7]
DBM (and trazodone) slow disease progression by preventing the cessation of protein synthesis in neurons.[8]