Dibenzoylmethane (DBM) is an

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...

with the formula (C₆H₅C(O))₂CH₂. DBM is the name for a 1,3-

diketone In organic chemistry, a dicarbonyl is a molecule containing two carbonyl () groups. Although this term could refer to any organic compound containing two carbonyl groups, it is used more specifically to describe molecules in which both carbonyls ...

, but the compound exists primarily as one of two equivalent

enol In organic chemistry, alkenols (shortened to enols) are a type of reactive structure or intermediate in organic chemistry that is represented as an alkene ( olefin) with a hydroxyl group attached to one end of the alkene double bond (). The te ...

tautomer Tautomers () are structural isomers (constitutional isomers) of chemical compounds that readily interconvert. The chemical reaction interconverting the two is called tautomerization. This conversion commonly results from the relocation of a hydr ...

s. DBM (actually its enol) is a white solid. Due to their high photostability and UV-absorbing properties, derivatives of DBM such as

avobenzone Avobenzone (trade names Parsol 1789, Milestab 1789, Eusolex 9020, Escalol 517, Neo Heliopan 357 and others, INCI Butyl Methoxydibenzoylmethane) is an oil-soluble ingredient used in sunscreen products to absorb the full spectrum of UVA rays. Hi ...

, have found applications as

sunscreen Sunscreen, also known as sunblock or sun cream, is a photoprotective topical product for the skin that mainly absorbs, or to a much lesser extent reflects, some of the sun's ultraviolet (UV) radiation and thus helps protect against sunburn and ...

products.

Synthesis and reactions

DBM is prepared by condensation of ethyl benzoate with

acetophenone Acetophenone is the organic compound with the formula C6H5C(O)CH3. It is the simplest aromatic ketone. This colorless, viscous liquid is a precursor to useful resins and fragrances. Production Acetophenone is formed as a byproduct of the cumene p ...

. Like other 1,3-diketones (or their enols), DBM condenses with a variety of bifunctional reagents to give heterocycles. Hydrazine gives diphenyl

pyrazole Pyrazole is an organic compound with the formula C3H3N2H. It is a heterocycle characterized by a 5-membered ring of three carbon Carbon () is a chemical element with the symbol C and atomic number 6. It is nonmetallic and tetravalent ...

. 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 Metal acetylacetonates are coordination complexes derived from the acetylacetonate anion () and metal ions, usually transition metals. The bidentate ligand acetylacetonate is often abbreviated acac. Typically both oxygen atoms bind to the metal t ...

Occurrence and medicinal properties

left, 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). It is also found in Curcumin. These occurrences have led to investigations into the medicinal properties of this class of compounds. DBM (and

Trazodone Trazodone, sold under many brand names, is an antidepressant medication. It is used to treat major depressive disorder, anxiety disorders, and difficulties with sleep. The medication is taken orally. Common side-effects include dry mouth, fe ...

) slow disease progression by preventing the cessation of protein synthesis in neurons.{{cite journal , doi=10.1093/brain/awx074, title=Repurposed Drugs Targeting eIF2α-P-Mediated Translational Repression Prevent Neurodegeneration in Mice, year=2017, last1=Halliday, first1=Mark, last2=Radford, first2=Helois, last3=Zents, first3=Karlijn A. M., last4=Molloy, first4=Collin, last5=Moreno, first5=Julie A., last6=Verity, first6=Nicholas C., last7=Smith, first7=Ewan, last8=Ortori, first8=Catharine A., last9=Barrett, first9=David A., last10=Bushell, first10= Martin, last11=Mallucci, first11=Giovanna R., journal=Brain, volume=140, issue=6, pages=1768–1783, pmid=28430857, pmc=5445255

Related compounds

* Benzoylacetone

References

Aromatic ketones Chelating agents Ligands Phenyl compounds