Synthesis and spectroscopic examination of various substituted 1,3-dibenzoylmethane, active agents for UVA/UVB photoprotection.
We describe the synthesis of eighteen variously substituted 1,3- dibenzoylmethane (1,3-DBM) and their change in absorption spectra depending of the nature of donor or acceptor substituents on one or the two aromatic moieties. These compounds were prepared in two steps starting from the corresponding acetophenones, phenol and benzoyl chlorides. The phenyl benzoate was obtained by condensation of benzoyl chloride with phenol in a classical way. Stirring of the phenyl benzoate and acetophenone in DMSO with powdered sodium hydroxide for a few minutes gave the dibenzoylmethane in yields depending on substituents on the phenyl rings. Changes in absorption of UVA/UVB sunlight of these molecules were observed according to the nature and the position of substituents on the phenyl rings. Molecules 2b (1-phenyl-3-(3,4,5-trimethoxyphenyl)-1,3-propanedione), 2d (1-(3,4-dimethoxyphenyl)-3-phenyl-l,3-propanedione), 2e (1-(2,3-dimethoxyphenyl)-3-phenyl-l,3-propanedione) and 2f (1-(2,3,4-trimethoxyphenyl)-3-phenyl-l,3-propanedione) were the most interesting for cosmetic applications because even after irradiation, they preserve their absorptive in UVA range and also in UVB range The other compounds are too photounstable and so can lose their protective effects. These results showed the lack of phototoxicity of these compounds and the possibility to use them as solar filters. Therefore, variously di- or tri methoxy 1,3-DBM are interesting molecules in term of photoprotection and open new prospects for UVA photostable filters.
Equipe Phytochimie, UMR CNRS 6263 Institut des Sciences Moléculaires de Marseille, Université Paul Cézanne (Aix-Marseille III), Avenue Escadrille Normandie Niémen, Case 461, 13397 Marseille Cedex 20, France.
Jean-Claude
JC
Hubaud
Isabelle
I
Bombarda
Laetitia
L
Decome
Jean-Claude
JC
Wallet
Emile M
EM
Gaydou
D000818:Animals; D047188:Chalcones / Q000138:chemical synthesis / Q000737:chemistry* / Q000633:toxicity; D051379:Mice; D012867:Skin / Q000528:radiation effects; D013473:Sunscreening Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000633:toxicity; D014466:Ultraviolet Rays
D047188:Chalcones; D013473:Sunscreening Agents; C061481:dibenzoylmethane