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 (actually its enol) is a white solid. Due to their high photostability and UV-absorbing properties, derivatives of DBM such as avobenzone, have found applications as sunscreen products.

Dibenzoylmethane
Names
Preferred IUPAC name
1,3-Diphenylpropane-1,3-dione
Other names
2-Benzoylacetophenone
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.003.999
UNII
  • 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
  • C1=CC=C(C=C1)C(=O)CC(=O)C2=CC=CC=C2
Properties
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).
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Infobox references

Synthesis and reactions

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

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).[4] It is also found in Curcumin. These occurrences have led to investigations into the medicinal properties of this class of compounds.[5][6]

DBM (and Trazodone) slow disease progression by preventing the cessation of protein synthesis in neurons.[7]

References
  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. 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.
  3. Magnani, Arthur; McElvain, S. M. (1940). "Dibenzoylmethane". Org. Synth. 20: 32. doi:10.15227/orgsyn.020.0032.
  4. Jackson, Kimberly M.; Deleon, Marisela; Verret, C.Reynold; Harris, Wayne B. (2002). "Dibenzoylmethane Induces Cell Cycle Deregulation in Human Prostate Cancer Cells". Cancer Letters. 178 (2): 161–165. doi:10.1016/S0304-3835(01)00844-8. PMID 11867200.
  5. Shishu; Singla, A.K.; Kaur, I.P. (2003). "Inhibitory Effect of Dibenzoylmethane on Mutagenicity of Food-Derived Heterocyclic Amine Mutagens". Phytomedicine. 10 (6–7): 575–582. doi:10.1078/094471103322331575. PMID 13678246.
  6. Pan, Min-Hsiung; Huang, Mei-Chen; Wang, Ying-Jan; Lin, Jen-Kun; Lin, Chao-Hsien (2003). "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". Journal of Agricultural and Food Chemistry. 51 (14): 3977–3984. doi:10.1021/jf034094i. PMID 12822933.
  7. Halliday, Mark; Radford, Helois; Zents, Karlijn A. M.; Molloy, Collin; Moreno, Julie A.; Verity, Nicholas C.; Smith, Ewan; Ortori, Catharine A.; Barrett, David A.; Bushell, Martin; Mallucci, Giovanna R. (2017). "Repurposed Drugs Targeting eIF2α-P-Mediated Translational Repression Prevent Neurodegeneration in Mice". Brain. 140 (6): 1768–1783. doi:10.1093/brain/awx074. PMC 5445255. PMID 28430857.
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