A new long-chain UV absorber derived from 4-tert-butyl-4′- methoxydibenzoylmethane: Absorbance stability under solar irradiation

Journal of Cosmetic Science

Volumn 56, Issue 2, 2005, Pages 135-148

  Wetz, F ^a   Routaboul, C ^b   Denis, A ^b   Rico Lattes, I ^a  

^a Université Paul Sabatier   (France)

^b BIODERMA   (France)

Author keywords

[No Author keywords available]

Indexed keywords

1 (4 TERT BUTYLPHENYL) 2 DECANYL 3 (4' METHOXYPHENYL)PROPANE; AVOBENZONE; COSMETIC; UNCLASSIFIED DRUG; XENON;

ARTICLE; IRRADIATION; LIGHT ABSORPTION; LIGHT EXPOSURE; PHOTOSTIMULATION; SOLAR RADIATION; SUNLIGHT; ULTRAVIOLET RADIATION;

CHALCONES; MAGNETIC RESONANCE SPECTROSCOPY; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROPHOTOMETRY, INFRARED; SUNLIGHT; SUNSCREENING AGENTS; ULTRAVIOLET RAYS;

EID: 19744366849     PISSN: 15257886     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (27)

1. International Agency for Research on Cancer, IARC Monographs on the Evaluation of Carcinogenic Risks to Humans: Solar and UV Radiation (IARC, Lyon, Vol. 55, 1992).
2. F. R. De Gruijl, H. J. Sterenborg, and P. D. Forbes, Wavelength dependence of skin cancer induction in albino hairless mice, Cancer Res., 53, 53-60 (1993).
3. W. Schwack and T. Rudolph, Photochemistry of dibenzoylmethane UVA filters. Part 1, J. Photochem. Photobiol. B: Biol., 28, 229-234 (1995).
4. M. Dubois, P. Tiercet, A. Deflandre, and M. A. Lefebvre, Photoisomerisation of the sunscreen filter Parsol 1789, J. Chim. Phys., 95, 388-394 (1998).
5. O. Karl-Fred De Polo, 4-(1,1-dimethylethyl)-4′- methoxydibenzoylmethane, US patent 4,387,089 (Givaudan Corporation, Clifton, NJ, 1983).
6. A. C. Weedon, "Photochemical Reactions Involving Enols," in The Chemistry of Enols, Zvi Rappoport Ed. (The Hebrew University, Jerusalem, 1990), pp. 602-633.
7. X. B. Chen and W. H. Fang, Norrish I vs II reactions of butanal: A combined CASSCF, DFT and MP2 study, Chem. Phys. Lett., 361, 473-482 (2002).
8. H. Sakurai and S. Kato, A theorical study of the Norrish type I reaction of acetone, J. Mol. Struct. (Theochem), 461-462, 145-152 (1999).
9. N. M. Roscher, M. K. O. Lindemann, S. B. Kong, C. G. Cho, and P. Jiang, Photodecomposition of several compounds commonly used as sunscreen agents, J. Photochem. Photobiol. A: Chem., 80, 417-421 (1994).
10. J. M. Allen, S. K. Allen, and B. Lingg, Photostabilities of several chemical compounds used as active ingredients in sunscreens. Drugs: Photochem., Photostabil., 225, 171-181 (1998).
11. J. N. Thorel, Procédé de photostabilisation du 4-(tert-butyl) 4′-méthoxy dibenzoylméthane, compositions filtrantes ainsi obtenues et leurs utilisations, FR patent 2 768 730 A1 (Paris, 1997).
12. D. Allard and S. Forestier, Compositions comprenant du 4-ter-butyl-4′-méthoxydibenzoylméthane, un dérivé de 1,3,5-triazine et un (alpha-cyano)-béta, béta′-diphénylacrylate d'alkyle et utilisations, FR patent 2 750 335 A1 (L'Oreal S.A., Paris, 1996).
13. I. Hansenne and K. De Chabannes, Composition filtrante photostable comprenant un dérivé de dibenzoylméthane et un alkylether de polysaccharide et ses utilisations, FR patent 2 747 038 A2 (L'Oreal S.A., Paris, 1996).
14. D. Candau, Cosmetic solar protection compositions based on a synergic mixture of filters and uses, WO 02/49598 A2 (L'Oreal S.A., Paris, 2001).
15. C. Cole and F. Natter, Sunscreen compositions containing a dibenzoylmethane derivative, US patent 6,444,195 B1 (Johnson & Johnson Consumer Companies, NJ, 2001).
16. S. Tobita, J. Ohba, K. Nakagawa, and H. Shizuka, Recovery mechanism of the reaction intermediate produced by photoinduced cleavage of the intramolecular hydrogen bond of dibenzoylmethane, J. Photochem. Photobiol. A: Chem., 92, 61-67 (1995).
17. M. J. Rosen, "Characteristic Features of Surfactants," in Surfactants and Interfacial Phenomena (Wiley Interscience, New York, 1989), pp. 1-32.
18. J. H. Clark and J. M. Miller, Hydrogen bonding in organic synthesis. Part 6. C-alkylation of β-dicarbonyl compounds using tetra-alkylammonium fluorides, J. C. S. Perkin I, 1743-1745 (1977).
19. J. H. Clark and J. M. Miller, Mono-C-alkylation of β-dicarbonyl compounds using tetraalkylammonium fluorides, J. C. S. Chem. Comm., 64-65 (1977).
20. A. L. Marzinzik and E. R. Felder, Solid support synthesis of highly functionalized pyrazoles and isoxazoles: Scaffolds for molecular diversity, Tetrahedron Lett., 37, 1003-1006 (1996).
21. T. Rudolph, Photoreactions of chemical UVA filters in cosmetics, GIT Laboratory J., 1, 17-20 (1997).
22. A. Deflandre and G. Lang, Photostability assessment of sunscreens: Benzylidene camphor and dibenzoylmethane derivatives, Int. J. Cosmet. Sci., 10, 53-62 (1988).
23. P. Markov and I. Petkov, On the photosensitivity of dibenzoylmethane, benzoylacetone and ethyl benzoylacetate in solution, Tetrahedron, 33, 1013-1015, (1977).
24. P. Markov, I. Petkov, and D. Jeglova, Photochemistry of enolizable β-dicarbonyl compounds: Study on the photoketonization of some esters of aroylacetic acids, J. Photochem., 8, 277-284 (1978).
25. J. Emsley, The composition, structure and hydrogen bonding of the β-diketones, Structure and Bonding, 57, 147-191 (1984).
26. H. Watarai, M. Takano, and N. Suzuki, Tautomerization and dissociation equilibria of β-diketones in microemulsions, Bull. Chem. Soc. Jpn., 65, 170-174 (1992).
27. F. Wetz, C. Routaboul, D. Lavabre, J.-C. Garrigues, I. Rico-Lattes, I. Pernet, and A. Denis, Photochemical behaviour of a new long-chain UV absorber derived from 4-tert-butyl-4′-methoxydibenzoylmethane, Photochem. Photobiol., 80, 316-321 (2004).