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Changes in Ultraviolet Absorption of Sunscreens After Ultraviolet Irradiation
Open accessAbstract
The incidence of skin cancer is increasing rapidly and sunscreens have been recommended in order to reduce damage from sunlight. In this investigation we have studied the change in the absorption spectrum of some photoactive organic species in sunscreens after ultraviolet A and ultraviolet B irradiation in a dose normally encountered during a full day in the sun. Samples of a number of photoactive compounds commonly used in sunscreens were irradiated with ultraviolet A and ultraviolet B light. A UVASUN 2000 MUTZHAS sunlamp was used for ultraviolet A irradiation and an Esshå Corona mini, equipped with two Philips TL12 20 W lamps, was used as the ultraviolet B source. The ultraviolet A dose was 100 J per cm2. The ultraviolet B dose corresponded to 20 minimal erythema doses. The absorption spectra of the compounds were recorded before and after irradiation. The absorbance of 2-ethylhexyl 4-methoxycinnamate was reduced significantly, whereas 3-(4-methylbenzyliden)camphor seemed to be rather stable. The benzophenones studied seemed to be relatively stable. In the case of 4-tert. butyl-4'-methoxy-dibenzoylmethane there was a rapid decrease in the ultraviolet A absorption leading to unsatisfactory protection in the ultraviolet A region. 4-Isopropyl-dibenzoylmethane also lost most of its ultraviolet protective capacity after irradiation with ultraviolet A. Ultraviolet B seemed to have a minor effect on all the samples. It is important for the clinician not only to know the initial absorption spectrum in the ultraviolet region for a specific sunscreen substance, but also whether it is altered during irradiation and in what way. This study including gas chromatography and mass spectrometry analysis indicates that some of the photoactive organic species commonly used today in sunscreens are unstable following ultraviolet irradiation.
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“It was verified that UV irradiation can promote the keto-enol isomerisation of 11 (Figure 2 (1)), and the fragmentation into two radicals (Figure 2 (2)), which after could form a phenacyl and benzoyl radicals that could generate reactive by-products, through reaction with others UV filters or fragments [28,30].”
From UV Filters: Challenges and Prospects (2022) · cites this paper as [30]
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“In 1999, Tarras-Wahlberg et al. verified by high-performance liquid chromatography (HPLC) analysis that samples of 21 previously irradiated with UVR (λ = 290–320 nm) showed the presence of an additional band associated with the Z isomer of the UV filter, confirming the conversion between E and Z isomers after UV exposure (Figure 3) [28,30].”
From UV Filters: Challenges and Prospects (2022) · cites this paper as [30]
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“The UV filter 3-(4-methylbenzylidene) camphor (4-MBC) (7) (Figure 1) suffers E-Z photoisomerisation. Nevertheless, 4-MBC (7) is considered stable due to the similarity of the UV spectra before and after irradiation, as well as the minimum change of the photoprotective action, before and after the irradiation [30].”
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“This compound tends to promptly decompose after irradiation, forming two photoproducts, one as a result of the loss of methyl group from the initial molecule, and the other product with an extra value of atomic number, probably associated with the oxidation of the amine group, directly linked to the aromatic ring (Table 1, 2nd entry) [30].”
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“The photodegradation of 2-ethylhexyl-4-dimethylaminobenzoate (Padimate O) (24) was also evaluated confirming its photoinstability for UVA and photostability for UVB radiation.”
From UV Filters: Challenges and Prospects (2022) · cites this paper as [30]
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Citations
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Cyclodextrin based novel drug delivery systems
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Sunscreens in human plasma and urine after repeated whole‐body topical application
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“Indeed, it is now well documented that dibenzoylmethanes lose much of their UV protective capacity after UV irradiation through tautomerization, fragmention and formation of new products with distinctly altered UV absorption characteristics (21,22).”
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Self-citationPerugini, P., Simeoni, S., Scalia, S., Genta, I., Modena, T., Conti, B., & Pavanetto, F. (2002) · International Journal of Pharmaceutics · doi:10.1016/s0378-5173(02)00356-3 · Cited by 164
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Dondi, D., Albini, A., & Serpone, N. (2006) · Photochemical & Photobiological Sciences · doi:10.1039/b606768a · Cited by 140
UV Filters: Challenges and Prospects
Jesus, A., Sousa, E., Cruz, M., Cidade, H., Lobo, J., & Almeida, I. (2022) · Pharmaceuticals · doi:10.3390/ph15030263 · Cited by 132
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“Despite the simplicity of these tests, the spectral profiles obtained on the UV-absorbers alone are in total accordance with literature data using other, sometimes more sophisticated means of investigation [15,31,47].”
BackgroundResultInfluentialPercutaneous absorption of benzophenone-3, a common component of topical sunscreens
Gonzalez, H. G., Farbrot, A., & Larkö, O. (2002) · Clinical and Experimental Dermatology · doi:10.1046/j.1365-2230.2002.01095.x · Cited by 121
Self-citationManová, E., von Goetz, N., Hauri, U., Bogdal, C., & Hungerbühler, K. (2012) · International Journal of Hygiene and Environmental Health · doi:10.1016/j.ijheh.2012.08.003 · Cited by 123
Photoisomerization of octyl methoxycinnamate
Pattanaargson, S., Munhapol, T., Hirunsupachot, P., & Luangthongaram, P. (2003) · Journal of Photochemistry and Photobiology A Chemistry · doi:10.1016/s1010-6030(03)00282-x · Cited by 116
Change of Ultraviolet Absorbance of Sunscreens by Exposure to Solar-Simulated Radiation
Maier, H., Hönigsmann, H., Schauberger, G., & Brunnhofer, K. (2001) · Journal of Investigative Dermatology · doi:10.1046/j.0022-202x.2001.01425.x · Cited by 113
“Photodecomposition of UV ®lters results in a change of absorptive capacity (Gasparro, 1985; Berset et al, 1995; Tarras-Wahlberg et al, 1999) and the development of photoproducts (Gasparro, 1985; Schwack and Rudolph, 1995), which might be of biologic relevance when sunscreens are applied as thin…”
BackgroundResultInfluentialUnexpected Photolysis of the Sunscreen Octinoxate in the Presence of the Sunscreen Avobenzone¶
Sayre, R. M., Dowdy, J. C., Gerwig, A. J., Shields, W. J., & Lloyd, R. V. (2005) · Photochemistry and Photobiology · doi:10.1562/2004-02-12-ra-083.1 · Cited by 111
Sunscreen use: controversies, challenges and regulatory aspects
Lodén, M., Beitner, H., Gonzalez, H., Edström, D. W., Åkerström, U., Austad, J., Buraczewska, I., Matsson, M., & Wulf, H. C. (2011) · British Journal of Dermatology · doi:10.1111/j.1365-2133.2011.10298.x · Cited by 110
Perioli, L., Ambrogi, V., Bertini, B., Ricci, M., Nocchetti, M., Latterini, L., & Rossi, C. R. (2005) · European Journal of Pharmaceutics and Biopharmaceutics · doi:10.1016/j.ejpb.2005.08.001 · Cited by 108
Photostability of commercial sunscreens upon sun exposure and irradiation by ultraviolet lamps
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“When mixed with petrolatum, some sunscreens undergo degradation during exposure to UV radiation, especially in the UVA range [5].”
BackgroundSelf-citationKarsili, T. N. V., Marchetti, B., Ashfold, M. N. R., & Domcke, W. (2014) · The Journal of Physical Chemistry A · doi:10.1021/jp507282d · Cited by 103
Ultraviolet Filters for Cosmetic Applications
Nițulescu, G., Lupuliasa, D., Adam-Dima, I., & Nițulescu, G. M. (2023) · Cosmetics · doi:10.3390/cosmetics10040101 · Cited by 113
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Stability of octyl methoxycinnamate and identification of its photo‐degradation product
Pattanaargson, S., & Limphong, P. (2001) · International Journal of Cosmetic Science · doi:10.1046/j.1467-2494.2001.00071.x · Cited by 84
“It has been speculated that a E to Z con¢guration change occurs upon light exposure [4,6].”
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Modern approaches to photoprotection
DeBuys, H. V., Levy, S. B., Murray, J. C., Madey, D. L., & Pinnell, S. R. (2000) · Dermatologic Clinics · doi:10.1016/s0733-8635(05)70208-4 · Cited by 80
Incorporation of quercetin in lipid microparticles: Effect on photo- and chemical-stability
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Functional photostability and cutaneous compatibility of bioactive UVA sun care products
de Oliveira, C. A., Peres, D. D., Rugno, C. M., Kojima, M., Pinto, C. A. S. D. O., Consiglieri, V. O., Kaneko, T. M., Rosado, C., Mota, J. P., Velasco, M. V. R., et al. (2015) · Journal of Photochemistry and Photobiology B Biology · doi:10.1016/j.jphotobiol.2015.04.007 · Cited by 78
“However, the critical wavelength values obtained were compatible with the BMDBM profile, indicating that rutin was not effective when associated with this UVA filter [8,11,23].”
BackgroundResultBallestín, S. S., & Bartolomé, M. J. L. (2023) · Applied Sciences · doi:10.3390/app13020712 · Cited by 64
Multiparticulate carriers for sun‐screening agents
Jain, S. K., & Jain, S. (2010) · International Journal of Cosmetic Science · doi:10.1111/j.1468-2494.2010.00547.x · Cited by 68
“Ultraviolet-induced photoageing accounts for 80–90% of visible skin ageing [3].”
BackgroundScalia, S., Molinari, A., Casolari, A., & Maldotti, A. (2004) · European Journal of Pharmaceutical Sciences · doi:10.1016/j.ejps.2004.03.014 · Cited by 70
Yener, G. (2003) · International Journal of Pharmaceutics · doi:10.1016/s0378-5173(03)00203-5 · Cited by 67
“All rights reserved. doi:10.1016/S0378-5173(03)00203-5 absorption spectra of the substance (Kammeyer et al., 1987; Aberturas et al., 1987; Tarras-Wahlberg et al., 1999).”
BackgroundInfluentialBerenbeim, J., Wong, N. G. K., Cockett, M., Berden, G., Oomens, J., Rijs, A., & Dessent, C. (2020) · Journal of Physical Chemistry A · doi:10.1021/acs.jpca.0c01295 · Cited by 55
Review of the environmental fate and effects of two UV filter substances used in cosmetic products
Duis, K., Junker, T., & Coors, A. (2022) · Science of The Total Environment · doi:10.1016/j.scitotenv.2021.151931 · Cited by 64
Huong, S. P., Rocher, E., Fourneron, J., Charles, L., Monnier, V., Bun, H., & Andrieu, V. (2007) · Journal of Photochemistry and Photobiology A Chemistry · doi:10.1016/j.jphotochem.2007.11.023 · Cited by 64
Wolf, R., Wolf, D., Morganti, P., & Ruocco, V. (2001) · Clinics in Dermatology · doi:10.1016/s0738-081x(01)00190-0 · Cited by 64
Scalia, S., Casolari, A., Iaconinoto, M. A., & Simeoni, S. (2002) · Journal of Pharmaceutical and Biomedical Analysis · doi:10.1016/s0731-7085(02)00433-8 · Cited by 65
Simeoni, S., Scalia, S., & Benson, H. A. (2004) · International Journal of Pharmaceutics · doi:10.1016/j.ijpharm.2004.05.021 · Cited by 64
A Perspective on the Ultrafast Photochemistry of Solution-Phase Sunscreen Molecules
Baker, L. A., Greenough, S. E., & Stavros, V. G. (2016) · The Journal of Physical Chemistry Letters · doi:10.1021/acs.jpclett.6b02104 · Cited by 57
A Survey of UV Filters Used in Sunscreen Cosmetics
Pniewska, A., & Kalinowska‐Lis, U. (2024) · Applied Sciences · doi:10.3390/app14083302 · Cited by 60
Ice-Catalyzed Ionization of Hydrochloric Acid
Bolton, K., & Pettersson, J. B. C. (2001) · Journal of the American Chemical Society · doi:10.1021/ja010096c · Cited by 56
Duale, N., Olsen, A.-K. H., Christensen, T., Butt, S. T., & Brunborg, G. (2010) · Toxicological Sciences · doi:10.1093/toxsci/kfq005 · Cited by 53
“The photoinstability of active ingredients in sunscreen has been reported by several studies (Bredholt et al., 1998; Serpone et al., 2002; Tarras-Wahlberg et al., 1999).”
Edlich, R. F., Winters, K. L., Lim, H. W., Cox, M. J., Becker, D. G., Horowitz, J. H., Nichter, L. S., Britt, L. D., & Long, W. B. (2004) · Journal of Long-Term Effects of Medical Implants · doi:10.1615/jlongtermeffmedimplants.v14.i4.40 · Cited by 52
Occurrence and Distribution of UV Filters in Beach Sediments of the Southern Baltic Sea Coast
Astel, A. M., Stec, M., & Rykowska, I. (2020) · Water · doi:10.3390/w12113024 · Cited by 51
“Since the International Agency for Research on Cancer (IARC) classified solar radiation (UV-B and UV-A) as human carcinogens [4], UV-filters containing creams, balms, and suntan lotions have been recommended by dermatologists as an effective means to protect the skin from excessive UV radiation, simultaneously prevent…”
BackgroundUp-to-Date Overview of the Use of Natural Ingredients in Sunscreens
Resende, D. I. S. P., de Jesus, A. I. M., Lobo, J. M. S., Sousa, E., Cruz, M. T., Cidade, H. M., & Almeida, I. F. (2022) · Pharmaceuticals · doi:10.3390/ph15030372 · Cited by 59
“Additionally, results showed the chemical stabilization of EHMC [68], a UVB filter commonly used in sunscreen formulations, known to be photounstable [70].”
BackgroundDamiani, E., Astolfi, P., Giesinger, J., Ehlis, T., Herzog, B., Greci, L., & Baschong, W. (2010) · Free Radical Research · doi:10.3109/10715760903486065 · Cited by 52
“This loss in photo-stability is in accordance with the earlier reports on BMDBM when in certain sunscreen formulations [10,37] and is attributed to the wellestablished keto-enol isomerization upon UV exposure (the diketo tautomer of BMDBM absorbs at 260 nm) followed by photo-cleavage leading to radical generation [16,…”
ResultSunscreen tests: Correspondence between in vitro data and values reported by the manufacturers
Garoli, D., Pelizzo, M. G., Bernardini, B., Nicolosi, P., & Alaibac, M. (2008) · Journal of Dermatological Science · doi:10.1016/j.jdermsci.2008.06.010 · Cited by 49
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Nanocarriers and Microcarriers for Enhancing the UV Protection of Sunscreens: An Overview
Damiani, E., & Puglia, C. (2019) · Journal of Pharmaceutical Sciences · doi:10.1016/j.xphs.2019.09.009 · Cited by 48
Li, C. C., Chen, Y. T., Lin, Y., Sie, S.-Y., & Chen-Yang, Y. W. (2013) · Colloids and Surfaces B Biointerfaces · doi:10.1016/j.colsurfb.2013.11.011 · Cited by 48
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Enhancement of melatonin photostability by encapsulation in lipospheres
Tursilli, R., Casolari, A., Iannuccelli, V., & Scalia, S. (2005) · Journal of Pharmaceutical and Biomedical Analysis · doi:10.1016/j.jpba.2005.08.025 · Cited by 48
Influence of liposphere preparation on butyl-methoxydibenzoylmethane photostability
Iannuccelli, V., Sala, N., Tursilli, R., Coppi, G., & Scalia, S. (2006) · European Journal of Pharmaceutics and Biopharmaceutics · doi:10.1016/j.ejpb.2006.01.007 · Cited by 47
Ambrogi, V., Latterini, L., Marmottini, F., Pagano, C., & Ricci, M. (2013) · Journal of Pharmaceutical Sciences · doi:10.1002/jps.23478 · Cited by 47
Armeni, T., Damiani, E., Battino, M. A., Greci, L., & Principato, G. (2004) · Toxicology · doi:10.1016/j.tox.2004.06.008 · Cited by 46
Photophysical characterization of cinnamates
Karpkird, T. M., Wanichweacharungruang, S., & Albinsson, B. (2009) · Photochemical & Photobiological Sciences · doi:10.1039/b909695g · Cited by 44
Aspée, A., Aliaga, C., & Scaiano, J. C. (2007) · Photochemistry and Photobiology · doi:10.1562/2006-08-01-ra-992 · Cited by 43
Tursilli, R., Piel, G., Delattre, L., & Scalia, S. (2007) · European Journal of Pharmaceutics and Biopharmaceutics · doi:10.1016/j.ejpb.2007.02.017 · Cited by 43
de Jesus, A. I. M., Augusto, I., Duarte, J., Sousa, E., Cidade, H. M., Cruz, M. T., Lobo, J. M. S., & Almeida, I. F. (2022) · Applied Sciences · doi:10.3390/app122312003 · Cited by 50
“Phenacyl and benzoyl radicals are the main photodegradation products formed; however, their combination could generate more reactive and toxic species for human beings and the environment [25,26], thus losing its photoprotective action [25].”
BackgroundScalia, S., & Mezzena, M. (2009) · AAPS PharmSciTech · doi:10.1208/s12249-009-9217-2 · Cited by 44
Kockler, J., Oelgemöller, M., Robertson, S. G., & Glass, B. D. (2014) · Cosmetics · doi:10.3390/cosmetics1020128 · Cited by 40
“in Scandinavia [24,25].”
Campos, P. M. B. G. M., Gianeti, M. D., Kanashiro, A., Lucisano-Valim, Y. M., & Gaspar, L. R. (2006) · Photochemistry and Photobiology · doi:10.1562/2005-10-14-ra-715 · Cited by 40
“Maia Campos) UV-induced erythema and, as shown by many studies, their regular use prevents skin photodamage (2).”
BackgroundScalia, S., Tursilli, R., & Iannuccelli, V. (2007) · Journal of Pharmaceutical and Biomedical Analysis · doi:10.1016/j.jpba.2007.01.016 · Cited by 43
Albertini, B., Mezzena, M., Passerini, N., Rodriguez, L., & Scalia, S. (2008) · Journal of Pharmaceutical Sciences · doi:10.1002/jps.21636 · Cited by 42
Pescia, A. C., Astolfi, P., Puglia, C., Bonina, F. P., Perrotta, R. E., Herzog, B., & Damiani, E. (2012) · International Journal of Pharmaceutics · doi:10.1016/j.ijpharm.2012.02.001 · Cited by 39
In vitro photostability and photoprotection studies of a novel ‘multi-active' UV-absorber
Venditti, E., Spadoni, T., Tiano, L., Astolfi, P., Greci, L., Littarru, G. P., & Damiani, E. (2008) · Free Radical Biology and Medicine · doi:10.1016/j.freeradbiomed.2008.04.025 · Cited by 39
“[34] reported that OMCdecomposes slightly after UV-B irradiation, but much more rapidly upon UV-A exposure supporting the results shown here.”
ResultBrugè, F., Tiano, L., Astolfi, P., Emanuelli, M., & Damiani, E. (2014) · PLoS ONE · doi:10.1371/journal.pone.0083401 · Cited by 40
“This loss in photostability is in accordance with previous reports on this UV filter present in certain sunscreen formulations [35,36], and is due to the well known keto-enol isomerisation upon UV exposure which is followed by photo-cleavage and generation of free radicals [9,37,38].”
ResultPoly( D,L ‐lactide) nanoencapsulation to reduce photoinactivation of a sunscreen agent
Vettor, M., Perugini, P., Scalia, S., Conti, B., Genta, I., Modena, T., & Pavanetto, F. (2008) · International Journal of Cosmetic Science · doi:10.1111/j.1468-2494.2008.00443.x · Cited by 38
“The applied UVB energy corresponded to 20 Minimal Erythemal Doses, which is considered comparable with a daily solar emission [24].”
BackgroundCarvalho, P. G., Naveira, R. I., Granone, L. I., Mendive, C. B., Massa, Á. E., & Churio, M. S. (2023) · Environmental Advances · doi:10.1016/j.envadv.2023.100404 · Cited by 37
Unexpected Photolysis of the Sunscreen Octinoxate in the Presence of the Sunscreen Avobenzone¶
Sayre, R. M., Dowdy, J. C., Gerwig, A. J., Shlelds, W. J., & Lioyd, R. V. (2005) · Photochemistry and Photobiology · doi:10.1111/j.1751-1097.2005.tb00207.x · Cited by 36
“0 2005 American Society for Photobiology 0031-8655/05 developed, highly effective dibenzoylmethane UV-A sunscreens was the focus of concern (2,9-16).”
BackgroundMaier, H., Schauberger, G., Martincigh, B. S., Brunnhofer, K., & Hönigsmann, H. (2005) · Photodermatology Photoimmunology & Photomedicine · doi:10.1111/j.1600-0781.2005.00143.x · Cited by 36
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“10,11 However, organic formulations are generally more esthetically appealing due to their inconspicuous appearance.”
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“uration does not allow the highest level of absorption of UV light energy (Tarras-Wahlberg et al., 1999; Pattanaargson and Limphong, 2001).”
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“[31] Tarras-Wahlberg N, Stenhagen G, Larko O, Rosén A,”
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“In earlier studies, B3 was proved to be reasonably photostable (23); other sunscreens have also been proved to be unstable (24,25).”
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“[13].”
Metadata
- Authors
- Tarras-Wahlberg, N., Rosén, A., Stenhagen, G., Larkö, O., Wennberg, A.-M., & Wennerström, O.
- Affiliations
- Chalmers University of Technology (SE)
- Sahlgrenska University Hospital (SE)
- Corresponding author
- Tarras-Wahlberg, Nils
- ORCID
- Stenhagen, Gunnar
- Venue
- Journal of Investigative Dermatology
- Publisher
- Elsevier BV
- Published
- 1999-10
- Volume
- 113
- Issue
- 4
- Pages
- 547-553
- ISSN
- 0022-202X (ISSN-L)
- OpenAlex
- W2075524385
- Cited by
- 172
- References
- 13
- Citations by year
- 2026: 2 · 2025: 2 · 2024: 5 · 2023: 5 · 2022: 6 · 2021: 1 · 2020: 10 · 2019: 5 · 2018: 5 · 2017: 4 · 2016: 8 · 2015: 5 · 2014: 9 · 2013: 11 · 2012: 6
- FWCI
- 5.45
- Type
- journal article
- Language
- en
- Open access
- bronze
- doi.org
- Licence
- Locations
- Journal of Investigative Dermatology (publishedVersion)
- PubMed (publishedVersion)
- Funders
- Vetenskapsrådet
- Topics
- Health Sciences › Medicine › Dermatology › Skin Protection and Aging
- Physical Sciences › Materials Science › Materials Chemistry › Photochromic and Fluorescence Chemistry
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Cell Biology › melanin and skin pigmentation
- Keywords
- sunscreen, UV absorption, photostability, UVA, UV-B radiation, 2-ethylhexyl-4-methoxycinnamate, benzophenone, skin cancer prevention
- MeSH terms
- Drug Stability, Spectrophotometry, Ultraviolet, Sunscreening Agents, Ultraviolet Rays
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