Dibenzoylmethane

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]

Dibenzoylmethane

Names
Preferred IUPAC name 1,3-Diphenylpropane-1,3-dione
Other names 2-Benzoylacetophenone
Identifiers
CAS Number	120-46-7 Y
3D model (JSmol)	Interactive image
ChemSpider	8126 N
ECHA InfoCard	100.003.999
PubChem CID	8433
UNII	ANS7ME8OKC Y
CompTox Dashboard (EPA)	DTXSID3041247
InChI InChI=1S/C15H12O2/c16-14(12-7-3-1-4-8-12)11-15(17)13-9-5-2-6-10-13/h1-10H,11H2 N Key: NZZIMKJIVMHWJC-UHFFFAOYSA-N N InChI=1/C15H12O2/c16-14(12-7-3-1-4-8-12)11-15(17)13-9-5-2-6-10-13/h1-10H,11H2 Key: NZZIMKJIVMHWJC-UHFFFAOYAS
SMILES C1=CC=C(C=C1)C(=O)CC(=O)C2=CC=CC=C2
Properties
Chemical formula	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). N verify (what is YN ?) Infobox references

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

Curcumin, structurally related to DBM, is the bright yellow component of the spice turmeric.

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]

Related compounds

• Benzoylacetone