Dibenzoylmethane
{{Chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 458774030
| ImageFile = DBMHenol.png
| ImageSize = 190
| PIN = 1,3-Diphenylpropane-1,3-dione
| OtherNames = 2-Benzoylacetophenone
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo =120-46-7
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = ANS7ME8OKC
| PubChem =8433
| SMILES = C1=CC=C(C=C1)C(=O)CC(=O)C2=CC=CC=C2
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 8126
| 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
| InChIKey = NZZIMKJIVMHWJC-UHFFFAOYAS
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C15H12O2/c16-14(12-7-3-1-4-8-12)11-15(17)13-9-5-2-6-10-13/h1-10H,11H2
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = NZZIMKJIVMHWJC-UHFFFAOYSA-N
}}
|Section2={{Chembox Properties
| Formula =C15H12O2
| MolarMass =224.25 g/mol
| Appearance = white solid
| Density = 1.334 g/cm3
| MeltingPtC = 77 to 78
| BoilingPt =
| Solubility = }}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
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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.{{cite journal|author1=Thomas, L. H. |author2=Florence, A. J. |author3=Wilson, C. C. |title=Hydrogen atom behaviour imaged in a short intramolecular hydrogen bond using the combined approach of X-ray and neutron diffraction|journal=New Journal of Chemistry|year=2009|volume=33|issue=12|pages=2486–2490|doi=10.1039/B908915B}} DBM is a white solid. Due UV-absorbing properties, derivatives of DBM such as avobenzone, have found applications as sunscreen products.{{Cite thesis |last=Freire |first=Thamires Batello |title=Influência de antioxidantes na fotoestabilização da avobenzona (filtro UVA) e do >i/i |date=2022-01-17 |degree=Doutorado em Produção e Controle Farmacêuticos |publisher=Universidade de São Paulo |url=https://www.teses.usp.br/teses/disponiveis/9/9139/tde-19052022-110821/ |place=São Paulo |doi=10.11606/t.9.2022.tde-19052022-110821 |language=pt|doi-access=free }}
Synthesis and reactions
DBM is prepared by condensation of ethyl benzoate with acetophenone.{{cite journal|title=Dibenzoylmethane|first1=Arthur|last1=Magnani|first2=S. M.|last2=McElvain|journal=Org. Synth.|year=1940|volume=20|pages=32|doi=10.15227/orgsyn.020.0032}}
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|date=April 2024}}
Occurrence and medicinal properties
file:curcumin.svg, 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).{{cite journal |doi=10.1016/S0304-3835(01)00844-8|title=Dibenzoylmethane Induces Cell Cycle Deregulation in Human Prostate Cancer Cells|year=2002|last1=Jackson|first1=Kimberly M.|last2=Deleon|first2=Marisela|last3=Verret|first3=C.Reynold|last4=Harris|first4=Wayne B.|journal=Cancer Letters|volume=178|issue=2|pages=161–165|pmid=11867200}} It is also found in Curcumin. These occurrences have led to investigations into the medicinal properties of this class of compounds.{{cite journal |doi=10.1078/094471103322331575|title=Inhibitory Effect of Dibenzoylmethane on Mutagenicity of Food-Derived Heterocyclic Amine Mutagens|year=2003|last1=Shishu|last2=Singla |first2=A.K.|last3=Kaur|first3=I.P.|journal=Phytomedicine|volume= 10|issue=6–7|pages=575–582|pmid= 13678246}}{{cite journal |doi=10.1021/jf034094i|title=Induction of Apoptosis by Hydroxydibenzoylmethane through Coordinative Modulation of Cyclin D3, BCL-XL, and Bax, Release of Cytochrome c, and Sequential Activation of Caspases in Human Colorectal Carcinoma Cells|year=2003|last1=Pan|first1=Min-Hsiung|last2=Huang|first2=Mei-Chen|last3=Wang|first3=Ying-Jan|last4=Lin|first4=Jen-Kun|last5=Lin|first5=Chao-Hsien|journal=Journal of Agricultural and Food Chemistry|volume=51|issue=14|pages=3977–3984|pmid=12822933}}
DBM (and trazodone) 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}}