Dibenzoylmethane

Dibenzoylmethane
Names
	IUPAC name 1,3-diphenylpropane-1,3-dione
	Other names 2-Benzoylacetophenone
Identifiers
CAS Number	120-46-7 ;
3D model (JSmol)	Interactive image;
ChemSpider	8126 ;
ECHA InfoCard	100.003.999
PubChem CID	8433;
CompTox Dashboard (EPA)	DTXSID3041247 ;
	InChI 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 Key: NZZIMKJIVMHWJC-UHFFFAOYSA-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;
	SMILES C1=CC=C(C=C1)C(=O)CC(=O)C2=CC=CC=C2;
Properties
Chemical formula	C15H12O2
Molar mass	224.25 g/mol
Melting point	77 to 78 °C (171 to 172 °F; 350 to 351 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). "`UNIQ--ref-00000014-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

^ ^a ^b [1], Jan Zawadiak, Marek Mrzyczek; Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 75 (2010) pp. 925-929
^ 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.

[Spectro-1] [1], Jan Zawadiak, Marek Mrzyczek; Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 75 (2010) pp. 925-929

[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.

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