SOLVENT EFFECT ON PHOTOSTABILITY OF BUTYL METHOXY DI BENZOYL METHANE FORMULATED IN SOLUTION AND EMULSION
Objective: The current study was undertaken to correlate the impact of some cosmetics solvents in the photostability of butyl methoxy dibenzoyl methane (BMDBM) into systems with an increasing order of complexity, from simple solutions to emulsions.
Methods: Solutions and emulsions containing BMDBM in different solvents were prepared and evaluated using spectrophotometer or transmittance analyzer, respectively. Also, emulsions containing BMDBM in combination with octyl methoxycinnamate (OMC) in ratio 1:1 and 1: 2, and in the presence of octocrylene in the ratio 1:2:1 were prepared. The percentage of decay absorbance at 356 nm was measured before and after irradiation at 500 W/m2 at intervals of 20 min until completing 100 min. Finally, a photolysis assay was carried to analyze deoxygenated and not BMDBM solutions.
Results: The absorbance decay of BMDBM in solution was higher in solvents such as mineral oil, isopropyl palmitate and isopropyl myristate. Also, it was observed that concentration and degassing had an effect on the decay kinetics. In emulsions containing only, BMDBM, the absorbance decay did not exceed 20% in all solvents, suggesting a protective effect of the matrix. In the contrary, a decay of 90% was observed in emulsion containing BMDBM and OMC in a 1:2 ratio. When Oct was added to that emulsion, stabilization on the absorbance decay of BMDBM was detected.
Conclusion: This study evidenced that the photochemistry of BMDBM is different in solutions and in emulsions. In solutions, the nature of solvents was important, while in emulsions the nature of UVB filters played a pivotal role in the stability of BMDBM.
2. S Kale, K Kulkarni, P Ugale, K Jadav. Application of hptlc for the qualitative and quantitative analysis of avobenzone, Oxybenzone, Octinoxate in sunscreen cream. Int J Pharm Pharm Sci 2014;6:391â€“4.
3. J Kockler, M OelgemÃ¶ller, S Robertson, BD Glass. Influence of titanium dioxide particle size on the photostability of the chemical UV-Filters butyl methoxy dibenzoylmethane and octocrylene in a microemulsion. Cosmetics 2014;1:128â€“39.
4. A Cantrell, D McGarvey. Photochemical studies of 4-tert-butyl-4â€™-methoxydibenzoyl methane (BM-DBM). J Photochem Photobiol B 2001;64:117â€“22.
5. W Schwack, T Rudolph. Photochemistry of dibenzoyl methane UVA filters Part 1. J Photochem Photobiol B 1995;28:229â€“34.
6. M Yamaji, C Paris, MÃ Miranda. Steady-state and laser flash photolysis studies on photochemical formation of 4-tert-butyl-4â€²-methoxydibenzoylmethane from its derivative via the norrish type II reaction in solution. J Photochem Photobiol A 2010;209:153â€“7.
7. M Yamaji, M Kida. Photothermal tautomerization of a UV sunscreen (4-tert-butyl-4Â´-methoxydibenzoylmethane) in acetonitrile studied by steady-state and laser flash photolysis. J Phys Chem 2013;117:1946â€“51.
8. Kockler J, Robertson S, OelgemÃ¶ller M, Davies M, Bowden B, Brittain HG, et al. Butyl methoxy dibenzoylmethane. Profiles of drug substances, Excipients and related methodology. 1st ed. Elsevier Inc, all rights reserved; 2013. p. 87-111.
9. JF Nash, PR Tanner. Relevance of UV filter/sunscreen product photostability to human safety. Photodermatol Photoimmunol Photomed 2014;30:88â€“95.
10. S Afonso, K Horita, J Sousa, I Almeida, M Amaral, P LobÃ£o, et al. Photodegradation of avobenzone: stabilization effect of antioxidants. J Photochem Photobiol B 2014;140:36â€“40.
11. C Gallardo, J Pinillos, J Arteaga, A Munera. Characterization of encapsulation process of avobenzone in solid lipid microparticle using a factorial design and its effect on photostability. J Appl Pharm Sci 2014;4:35â€“43.
12. C Gallardo, J Vallejo, M Mesa. Evaluation of the avobenzone photostability in solvents used in cosmetic formulations. Vitae 2011;18:63â€“71.
13. H Maier, A Schmalwieser. Sunscreens and occupation: the austrian experience. Photochem Photobiol Sci 2010;9:510â€“5.
14. G Neudahl, J Zhang. Formulating sun protection products that people will use with favourable aesthetics. Focus Sun Care 2010;3:18â€“20.
15. S Huong, E Rocher, J Fourneron, L Charles, V Monnier, H Bun, et al. Photoreactivity of the sunscreen Butyl methoxy di benzoyl methane (DBM) under various experimental conditions. J Photochem Photobiol A 2008;196:106â€“12.
16. U Craig, C Bonda, A Pavlovic. Photostabilizers, UV absorbers, and methods of photostabilizing a sunscreen composition. U. S. Patent No.â€ 6,962,692; 2005.
17. O Dueva, J Sanogueira. Sunscreen compositions with SPF enhancer. U. S. Patent No 8,465,729; 2013.
18. B Brewster. Photostability: the back story of UV Filters. Cosmet Toilet 2006;121:22â€“8.
19. B Buzek, Ask. Regulation (EC) No 1223/2009 of the european parliament and of the council of 30 november 2009 on cosmetic products. Off J Eur Union L 2009;342:133.
20. G Mturi, B Martincigh. Photostability of the sunscreening agent 4-tert-butyl-4â€²-methoxydibenzoylmethane (avobenzone) in solvents of different polarity and proticity. J Photochem Photobiol A 2008;200:410â€“20.
21. M Dubois, P Gilard, P Tiercet, A Deflandre, M Lefebvre. Photoisomerisation of the sunscreen filter PARSOLÂ® 1789. J Chim Phys 1998;95:388â€“94.
22. G Marti-mestres, C Fernandez, N Parsotam, F Nielloud, J Mestres, H Maillols. Stability of UV filters in different vehicles: solvents and emulsions. Drug Dev Ind Pharm 1997;23:647â€“55.
23. L Gaspar, P Maia. Evaluation of the photostability of different UV filter combinations in a sunscreen. Int J Pharm 2006;307:123â€“8.
24. E Damiani, L Rosati, R Castagna, P Carloni, L Greci. Changes in ultraviolet absorbance and hence in protective efficacy against lipid peroxidation of organic sunscreens after UVA irradiation. J Photochem Photobiol B 2006;82:204â€“13.
25. G Niculae, N Badea, A Meghea, O Oprea, I Lacatusu. Coencapsulation of butyl-methoxydibenzoylmethane and octocrylene into lipid nanocarriers: UV performance, photostability and in vitro release. Photochem Photobiol 2013;89:1085-94.
26. R Rodil, M Moeder, R Altenburger, M Schmitt-Jansen. Photostability and phytotoxicity of selected sunscreen agents and their degradation mixtures in water. Anal Bioanal Chem 2009;395:1513â€“24.
27. A Ricci, M ChrÃ©tien, L Maretti, J Scaiano. TiO2-promoted mineralization of organic sunscreens in water suspension and sodium dodecyl sulfate micelles. Photochem Photobiol Sci 2003;2:487â€“92.
28. K Broadbent, B Martincigh, M Raynor, L Salter, R Moulder, P SjÃ¶berg, et al. Capillary supercritical fluid chromatography combined with atmospheric pressure chemical ionisation mass spectrometry for the investigation of photoproduct formation in the sunscreen absorber 2-ethylhexyl-p-methoxycinnamate. J Chromatogr A 1996;732:101â€“10.
29. C Bonda. The photostability of organic sunscreen actives. In: Shaath N. Sunscreens. 1Âª edition. Boca Raton: Taylor Francis; 2005. p. 323â€“45.
30. D Dondi, A Albini, N Serpone. Interactions between different solar UVB/UVA filters contained in commercial suncreams and consequent loss of UV protection. Photochem Photobiol Sci 2006;5:835â€“43.