Dibenzoylmethane (DBM) is an

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

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, enols are a type of functional group or intermediate in organic chemistry containing a group with the formula (R = many substituents). The term ''enol'' is an abbreviation of ''alkenol'', a portmanteau deriving from "-ene ...

tautomer In chemistry, 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 reloca ...

s. DBM is a white solid. Due 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, International Nomenclature of Cosmetic Ingredients, INCI Butyl Methoxydibenzoylmethane) is an organic molecule and an oil-soluble ingredie ...

, have found applications as

sunscreen Sunscreen, also known as sunblock, sun lotion or sun cream, is a photoprotection, photoprotective topical product for the Human skin, skin that helps protect against sunburn and prevent skin cancer. Sunscreens come as lotions, sprays, gels, fo ...

products.

Synthesis and reactions

DBM is prepared by

condensation Condensation is the change of the state of matter from the gas phase into the liquid phase, and is the reverse of vaporization. The word most often refers to the water cycle. It can also be defined as the change in the state of water vapor ...

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 ...

. 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 chemical formula, formula . It is a heterocycle characterized as an azole with a 5-membered ring of three carbon atoms and two adjacent nitrogen atoms, which are in Arene substitution pattern, ortho-substi ...

. 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 acetylacetone, acetylacetonate anion () and metal ions, usually transition metals. The bidentate ligand acetylacetonate is often abbreviated acac. Typically both oxygen atoms bind 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 is an antidepressant medication used to treat major depressive disorder, anxiety disorders, and insomnia. It is a phenylpiperazine compound of the serotonin antagonist and reuptake inhibitor (SARI) class. The medication is taken or ...

) 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