Dibenzoylmethane
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| Names | |
|---|---|
| IUPAC name
1,3-diphenylpropane-1,3-dione | |
| Other names
2-Benzoylacetophenone | |
| Identifiers | |
120-46-7  | |
| 3D model (Jmol) | Interactive image |
| ChemSpider | 8126  |
| ECHA InfoCard | 100.003.999 |
| PubChem | 8433 |
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| Properties | |
| C15H12O2 | |
| Molar mass | 224.25 g/mol |
| 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). | |
| "`UNIQ--ref-00000001-QINU`"'_&page2=Dibenzoylmethane verify (what is ?) | |
| Infobox references | |
1,3-Diphenyl-1,3-propanedione (dibenzoylmethane, DBM) is an aromatic 1,3-diketone derivative of acetylacetone (acac), where both methyl groups in acac have been substituted by phenyl groups. It is a white solid melting at 77−78 °C. Similar to acac, DBM exists in two tautomeric forms, with the keto-enol equilibrium of DBM shifting strongly towards the enol form, particularly in non-polar solvents such as benzene.[1] This is the result of the stability of the intramolecular hydrogen bond in the cis-enol form which is further resonance-stabilized by conjugation with phenyl rings. Due to its high photostability, derivatives of DBM such as avobenzone, have found applications as sunscreen products.
Dibenzoylmethane (DBM) is a natural phytochemical found as a minor constitute in the root extract of Licorice (Glycyrrhiza glabra in the family Leguminosae), it is a beta-diketone phytochemical with a wide variety of anti-cancer effects. DBM has been shown to prevent the formation of DNA-adducts induced by carcinogen in both in vitro and in vivo studies. DBM could induce apoptosis in human prostate and colon cancer cells , and induce cycle arrest in prostate cancer cells
References
- 1 2 , Jan Zawadiak, Marek Mrzyczek; Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 75 (2010) pp. 925-929