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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].”
From UV Filters: Challenges and Prospects (2022) · cites this paper as [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].”
From UV Filters: Challenges and Prospects (2022) · cites this paper as [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
Cites
Reduction of Solar Keratoses by Regular Sunscreen Use
Thompson, S., Jolley, D., & Marks, R. (1993) · New England Journal of Medicine · doi:10.1056/nejm199310143291602 · Cited by 782
Wavelengths effective in induction of malignant melanoma.
Setlow, R. B., Grist, E., Thompson, K. H., & Woodhead, A. D. (1993) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.90.14.6666 · Cited by 718
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Photochemistry of dibenzoyl methane UVA filters—Part 1
Schwack, W., & Rudolph, T. (1995) · Journal of Photochemistry and Photobiology B: Biology · doi:10.1016/1011-1344(95)07118-l · Cited by 180
Armstrong, B. K., Kricker, A., & English, D. R. (1997) · Australasian Journal of Dermatology · doi:10.1111/j.1440-0960.1997.tb01000.x · Cited by 179
Sunscreen Application and Its Importance for the Sun Protection Factor
Stenberg, C. (1985) · Archives of Dermatology · doi:10.1001/archderm.1985.01660110048013 · Cited by 169
Is the use of sunscreens a risk factor for malignant melanoma?
Westerdahl, J., Olsson, H. L., ck, A. M. S., Ingvar, C., & Jonsson, N. (1995) · Melanoma Research · doi:10.1097/00008390-199502000-00007 · Cited by 147
Ultraviolet radiation and skin cancer of humans
Urbach, F. (1997) · Journal of Photochemistry and Photobiology B: Biology · doi:10.1016/s1011-1344(97)00029-8 · Cited by 136
Photodecomposition of several compounds commonly used as sunscreen agents
Roscher, N. M., Lindemann, M. K. O., Bin Kong, S., Cho, C. G., & Jiang, P. (1994) · Journal of Photochemistry and Photobiology A: Chemistry · doi:10.1016/1010-6030(94)01043-9 · Cited by 101
Uric acid photo‐oxidation assay: in vitro comparison of sunscreening agents
Dunlap, W. C., Yamamoto, Y., Inoue, M., Kashiba-Iwatsuki, M., YAMAGUCHI, M., & TOMITA, K. (1998) · International Journal of Cosmetic Science · doi:10.1046/j.1467-2494.1998.171731.x · Cited by 32
Research works printed but not linked: 1
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Cited by
Sorted by citations
Inorganic and organic UV filters: Their role and efficacy in sunscreens and suncare products
Serpone, N., Dondi, D., & Albini, A. (2007) · Inorganica Chimica Acta · doi:10.1016/j.ica.2005.12.057 · Cited by 711
Cyclodextrin based novel drug delivery systems
Vyas, A., Saraf, S., & Saraf, S. (2008) · Journal of Inclusion Phenomena and Macrocyclic Chemistry · doi:10.1007/s10847-008-9456-y · Cited by 412
Hydrotalcite-like compounds: Versatile layered hosts of molecular anions with biological activity
Costantino, U., Ambrogi, V., Nocchetti, M., & Perioli, L. (2007) · Microporous and Mesoporous Materials · doi:10.1016/j.micromeso.2007.02.005 · Cited by 302
Kockler, J., Oelgemöller, M., Robertson, S., & Glass, B. D. (2012) · Journal of Photochemistry and Photobiology C: Photochemistry Reviews · doi:10.1016/j.jphotochemrev.2011.12.001 · Cited by 268
Sunscreens in human plasma and urine after repeated whole‐body topical application
Janjua, N., Kongshoj, B., Andersson, A., & Wulf, H. (2008) · Journal of the European Academy of Dermatology and Venereology · doi:10.1111/j.1468-3083.2007.02492.x · Cited by 252
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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