Dibenzoylmethane

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Dibenzoylmethane
Dibenzoylmethane.svg
Dibenzoylmethane-3D-balls-by-AHRLS-2012.png
Dibenzoylmethane-3D-vdW-by-AHRLS-2012.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
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

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), and 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. 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.[3]

References[edit]

  1. ^ a b 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. doi:10.1016/j.saa.2009.12.040. 
  2. ^ 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.
  3. ^ Repurposed drugs targeting eIF2α-P-mediated translational repression prevent neurodegeneration in mice - Brain, 19 April 2017