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 the enol tautomer. The interconversion between the diketone and the two equivalent enols is so rapid that the distinction is usually ignored. DBM (actually its enol) is a white solid. Due to their high photostability, derivatives of DBM such as avobenzone, have found applications as sunscreen products.

Dibenzoylmethane
DBMHenol.png
Names
IUPAC name
1,3-diphenylpropane-1,3-dione
Other names
2-Benzoylacetophenone
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.003.999
Properties
C15H12O2
Molar mass 224.25 g/mol
Appearance white solid
Density 1.334 g cm�3
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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Infobox references

Synthesis, structure, and reactionsEdit

DBM is prepared by condensation of ethyl benzoate with acetophenone.[2]

DBM always crystallizes as the enol.[3]

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.

OccurrenceEdit

Dibenzoylmethane (DBM) is a natural phytochemical found as a minor constituent in the root extract of Licorice (Glycyrrhiza glabra in the family Leguminosae). DBM has been shown to prevent the formation of DNA-adducts induced by carcinogens in both in vitro and in vivo studies. DBM induce apoptosis in human prostate and colon cancer cells, and induce cycle arrest in prostate cancer cells.[4]

An investigational use in the treatment of neurodegenerative diseases has been suggested; in the study DBM (and Trazodone) demonstrated potential in slowing disease progression, by preventing the cessation of protein synthesis in neurons.[5]

ReferencesEdit

  1. ^ Jan Zawadiak; Marek Mrzyczek (2010). "UV absorption and keto–enol tautomerism equilibrium of methoxy and dimethoxy 1,3-diphenylpropane-1,3-diones". Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 75 (2): 925–929. Bibcode:2010AcSpA..75..925Z. doi:10.1016/j.saa.2009.12.040. PMID 20047853.
  2. ^ Arthur Magnani, S. M. McElvain (1940). "Dibenzoylmethane". Org. Synth. 20: 32. doi:10.15227/orgsyn.020.0032.CS1 maint: uses authors parameter (link)
  3. ^ Thomas, L. H.; Florence, A. J.; Wilson, C. C. (2009). "Hydrogen atom behaviour imaged in a short intramolecular hydrogen bond using the combined approach of X-ray and neutron diffraction". New Journal of Chemistry. 33 (12): 2486–2490. doi:10.1039/B908915B.CS1 maint: uses authors parameter (link)
  4. ^ K. Singletary, C. MacDonald, Cancer Lett. 155 (2000) 47. Shishu, A.K. Singla, I.P. Kaur, Phytomedicine 10 (2003) 575. C.C. Lin, Y.P. Lu, Y.R. Lou, C.T. Ho, H.H. Newmark, C. MacDonald, K.W. Singletary, M.T. Huang, Cancer Lett. 168 (2001) 125. K. Singletary, C. MacDonald, M. Iovinelli, C. Fisher, M. Wallig, Carcinogenesis 19 (1998) 1039. M.H. Pan, M.C. Huang, Y.J. Wang, J.K. Lin, C.H. Lin, J. Agric. Food Chem. 51 (2003) 3977. K.M. Jackson, M. DeLeon, C.R. Verret, W.B. Harris, Cancer Lett. 178 (2002) 161.
  5. ^ Repurposed drugs targeting eIF2α-P-mediated translational repression prevent neurodegeneration in mice - Brain, 19 April 2017