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 enoltautomers.[2] DBM is a white solid. Due UV-absorbing properties, derivatives of DBM such as avobenzone, have found applications as sunscreen products.
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.[citation needed]
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]
^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. PMID20047853.
^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.
^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. PMID11867200.
^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. PMID13678246.
^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. PMID12822933.
