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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. 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.

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

thumb|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) slow disease progression by preventing the cessation of protein synthesis in neurons.

References

References

  1. (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.
  2. (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.
  3. Freire, Thamires Batello. (2022-01-17). "Influência de antioxidantes na fotoestabilização da avobenzona (filtro UVA) e do >i/i". Universidade de São Paulo.
  4. (1940). "Dibenzoylmethane". Org. Synth..
  5. (2002). "Dibenzoylmethane Induces Cell Cycle Deregulation in Human Prostate Cancer Cells". Cancer Letters.
  6. (2003). "Inhibitory Effect of Dibenzoylmethane on Mutagenicity of Food-Derived Heterocyclic Amine Mutagens". Phytomedicine.
  7. (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.
  8. (2017). "Repurposed Drugs Targeting eIF2α-P-Mediated Translational Repression Prevent Neurodegeneration in Mice". Brain.
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aromatic-ketones chelating-agents ligands phenyl-compounds
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