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Synthesis and spectroscopic examination of various substituted 1,3-dibenzoylmethane, active agents for UVA/UVB photoprotection

Paper ID Volume ID Publish Year Pages File Format Full-Text
30558 44486 2008 7 PDF Available
Title
Synthesis and spectroscopic examination of various substituted 1,3-dibenzoylmethane, active agents for UVA/UVB photoprotection
Abstract

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.

Keywords
1,3- dibenzoylmethane; Synthesis; UVA/UVB sunlight; Photoprotection; Photostable filters; Sunscreen
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Synthesis and spectroscopic examination of various substituted 1,3-dibenzoylmethane, active agents for UVA/UVB photoprotection
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Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Photochemistry and Photobiology B: Biology - Volume 92, Issue 2, 21 August 2008, Pages 103–109
Authors
, , , , ,
Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
Online Support
Any Questions? feel free to contact us