Photophysical properties of dioctyl 4-methoxybenzylidenemalonate: UV-B absorber

Photochemical and Photobiological Sciences

Volumn 11, Issue 10, 2012, Pages 1528-1535

  Oguchi Fujiyama, Nozomi ^a   Miyazawa, Kazuyuki ^a   Kikuchi, Azusa ^b   Yagi, Mikio ^b  

^a SHISEIDO RESEARCH CENTER   (Japan)

^b YOKOHAMA NATIONAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84871826682     PISSN: 1474905X     EISSN: 14749092     Source Type: Journal    
DOI: 10.1039/c2pp25101a     Document Type: Article

References (48)

1. United Nations Environment Programme Environmental Effects Assessment Panel Environmental effects of ozone depletion and its interactions with climate change: progress report, 2011, Photochem. Photobiol. Sci 2012 11 13 27
2. N. R. Attard P. Karran UVA photosensitization of thiopurines and skin cancer in organ transplant recipients Photochem. Photobiol. Sci. 2012 11 62 68
3. G. P. Pfeifer A. Besaratinia UV wavelength-dependent DNA damage and human non-melanoma and melanoma skin cancer Photochem. Photobiol. Sci. 2012 11 90 97
4. Y. Matsumura H. N. Ananthaswamy Toxic effects of ultraviolet radiation on the skin Toxicol. Appl. Pharmacol. 2004 195 298 308 (Pubitemid 38338650)
5. T. M. Hughes J. A. Martin V. J. Lewis N. M. Stone Allergic contact dermatitis to drometrizole trisiloxane in a sunscreen with concomitant sensitivities to other sun screens Contact Dermatitis 2005 52 226 227 (Pubitemid 40676602)
6. W. Schwack T. Rudolph Photochemistry of dibenzoyl methane UVA filters, Part 1 J. Photochem. Photobiol., B 1995 28 229 234
7. N. M. Roscher M. K. O. Lindemann S. B. Kong C. G. Cho P. Jiang Photodecomposition of several compounds commonly used as sunscreen agents J. Photochem. Photobiol., A 1994 80 417 421
8. J. M. Allen C. J. Gossett S. K. Allen Photochemical formation of singlet molecular oxygen in illuminated aqueous solutions of several commercially available sunscreen active ingredients Chem. Res. Toxicol. 1996 9 605 609 (Pubitemid 26123961)
9. L. F. Alves R. Gargano S. K. B. Alcanfor L. A. S. Romeiro J. B. L. Martins A chromophoric study of 2-ethylhexyl p-methoxycinnamate Chem. Phys. Lett. 2011 516 162 165
10. B. K. Paul N. Guchhait A computational insight into the photophysics of a potent UV absorber Tinuvin P: critical evaluation of the role of charge transfer interaction and topological properties of the intramolecular hydrogen bonding Comput. Theor. Chem. 2011 966 250 258
11. K. Morabito K. G. Steeley N. C. Shapley C. Mello D. Li P. Calvert A. Tripathi Proximal effects of ultraviolet light absorbers and polymer matrix in the photostability of β-carotene Dyes Pigm. 2012 92 509 516
12. A. Kikuchi M. Yagi Direct observation of the intermolecular triplet-triplet energy transfer from UV-A absorber 4-tert-butyl-4′- methoxydibenzoylmethane to UV-B absorber octyl methoxycinnamate Chem. Phys. Lett. 2011 513 63 66
13. A. Kikuchi H. Saito M. Mori M. Yagi Photoexcited triplet states of new UV absorbers, cinnamic acid 2-methylphenyl esters Photochem. Photobiol. Sci. 2011 10 1902 1909
14. A. Kikuchi S. Yukimaru N. Oguchi K. Miyazawa M. Yagi Excited triplet state of a UV-B absorber, octyl methoxycinnamate Chem. Lett. 2010 39 633 635
15. V. Lhiaubet-Vallet M. Marin O. Jimenez O. Gorchs C. Trullas M. A. Miranda Filter-filter interactions. Photostabilization, triplet quenching and reactivity with singlet oxygen Photochem. Photobiol. Sci. 2010 9 552 558
16. C. Bonda A. Pavlovic K. Hanson C. Bardeen Singlet quenching proves faster is better for photostability Cosmet. Toiletries 2010 125 40 48
17. R. Farkas V. Lhiaubet-Vallet J. Corbera M. Törincsi O. Gorchs C. Trullas O. Jiménez M. A. Miranda L. Novak Synthesis of new 2-(2′-hydroxyaryl)benzotriazoles and evaluation of their photochemical behavior as potential UV-filters Molecules 2010 15 6205 6216
18. J. Kockler M. Oelgemöller S. Robertson B. D. Glass Photostability of sunscreens J. Photochem. Photobiol., C 2012 13 91 110
19. 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 5 835 843 (Pubitemid 44315945)
20. C. A. Bonda, The Photostability of Organic Sunscreen Actives: A Review, in Sunscreens, ed., N. A. Shaath, Taylor & Francis, Boca Raton, 2005, pp. 321-349
21. C. Paris V. Lhiaubet-Vallet O. Jiménez C. Trullas M. Á. Miranda A blocked diketo form of avobenzone: photostability, photosensitizing properties and triplet quenching by a triazine-derived UVB-filter Photochem. Photobiol. 2009 85 178 184
22. S. Scalia M. Mezzena Photostabilization effect of quercetin on the UV filter combination, butyl methoxydibenzoylmethane-octyl methoxycinnamate Photochem. Photobiol. 2010 86 273 278
23. C. Mendrok-Edinger K. Smith A. Janssen J. Vollhardt The quest for avobenzone stabilizers and sunscreen photostability Cosmet. Toiletries 2009 124 47 54
24. B. Herzog M. Wehrle K. Quass Photostability of UV absorber systems in sunscreens Photochem. Photobiol. 2009 85 869 878
25. E. Damiani W. Baschong L. Greci UV-Filter combinations under UV-A exposure: Concomitant quantification of over-all spectral stability and molecular integrity J. Photochem. Photobiol., B 2007 87 95 104 (Pubitemid 46706304)
26. 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 82 204 213 (Pubitemid 43240101)
27. E. Chatelain B. Gabard Photostabilization of butyl methoxydibenzoylmethane (avobenzone) and ethylhexyl methoxycinnamate by bis-ethylhexyloxyphenol methoxyphenyl triazine (Tinosorb S), a new UV broadband filter Photochem. Photobiol. 2001 74 401 406
28. R. M. Sayre J. C. Dowdy A. J. Gerwig W. J. Shields R. V. Lloyd Unexpected photolysis of the sunscreen octinoxate in the presence of the sunscreen avobenzone Photochem. Photobiol. 2005 81 452 456 (Pubitemid 40551525)
29. N. A. Shaath Ultraviolet filters Photochem. Photobiol. Sci. 2010 9 464 469
30. S. Schauder H. Ippen Contact and photocontact sensitivity to sunscreens: Review of a 15-year experience and of the literature Contact Dermatitis 1997 37 221 232 (Pubitemid 27499880)
31. S. P. Huong V. Andrieu J.-P. Reynier E. Rocher J.-D. Fourneron The photoisomerization of the sunscreen ethylhexyl p-methoxy cinnamate and its influence on the sun protection factor J. Photochem. Photobiol., A 2007 186 65 70
32. S. Pattanaargson N. Hongchinnagorn P. Hirunsupachot Y. Sritana-anant UV absorption and photoisomerization of p-methoxycinnamate grafted silicone Photochem. Photobiol. 2004 80 322 325
33. S. Pattanaargson T. Munhapol P. Hirunsupachot P. Luangthongaram Photoisomerization of octyl methoxycinnamate J. Photochem. Photobiol., A 2004 161 269 274
34. W. Johncock Sunscreen interactions in formulations Cosmet. Toiletries 1999 114 75 82
35. Z. R. Grabowski A. Grabowska The Förster cycle reconsidered Z. Phys. Chem. 1976 101 197 208
36. A. Kikuchi N. Oguchi M. Yagi Optical and electron paramagnetic resonance studies of the excited states of 4-tert-butyl-4′-methoxydibenzoylmethane and 4-tert-butyl-4′-methoxydibenzoylpropane J. Phys. Chem. A 2009 113 13492 13497
37. M. Montalti, A. Credi, L. Prodi and M. T. Gandolfi, Handbook of photochemistry, Tayler & Francis, Boca Raton, 3rd edn, 2006
38. P. Kottis R. Lefebvre Calculation of the electron spin resonance line shape of randomly oriented molecules in a triplet state. I. The Δm = 2 transition with a constant linewidth J. Chem. Phys. 1963 39 393 403
39. 1 states of halogen-containing benzonitriles, anisoles and anilines Mol. Phys. 1978 35 1029 1046
40. G. Kothandaraman D. S. Tinti PMDR studies of intramolecular spin-orbit perturbations on the triplet state properties of substituted benzenes Chem. Phys. Lett. 1973 19 225 230
41. S. A. Boorstein M. Gouterman Theory for zero-field splittings in aromatic hydrocarbons. III J. Chem. Phys. 1963 39 2443 2452
42. W. T. Raynes Spin splittings and rotational structure of nonlinear molecules in doublet and triplet electronic states J. Chem. Phys. 1964 41 3020 3032
43. N. J. Turro, V. Ramamurthy and J. C. Scaiano, Modern Molecular Photochemistry of organic molecules, Unversity Science Books, Sausalito, 2010
44. g): quantum yields of formation and lifetimes J. Photochem. 1985 31 37 47
45. T. Suzuki U. Okuyama T. Ichimura Double proton transfer reaction of 7-azaindole dimer and complexes studied by time-resolved thermal lensing technique J. Phys. Chem. A 1997 101 7047 7052 (Pubitemid 127580960)
46. M. W. Wolf R. E. Brown L. A. Singer Deactivation of benzophenone triplets via exciplex formation. Evidence for dual reaction pathways J. Am. Chem. Soc. 1977 99 526 531
47. J. V. Morris M. A. Mahaney J. R. Huber Fluorescence quantum yield determinations. 9,10-Diphenylanthracene as a reference standard in different solvents J. Phys. Chem. 1976 80 969 974
48. T. M. Karpkird S. Wanichweacharungruang B. Albinsson Photophysical characterization of cinnamates Photochem. Photobiol. Sci. 2009 8 1455 1460