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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UV irradiation can promote keto-enol isomerisation of avobenzone and fragmentation into radicals that can form reactive by-products.
“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]
The “UVB sunscreen compounds” section (page not specified in our copy) says that the dibenzoylmethane derivative requires keto-enol isomerization before photoreaction and decomposes under UV irradiation. The Discussion describes possible secondary reactions in sunscreen mixtures, but the cited passages do not establish fragmentation into phenacyl and benzoyl radicals or their reactions with other UV filters. (LLM, conf=0.86)
Experimental — accuracy not yet measuredEHMC undergoes E-to-Z photoisomerisation after UV exposure at 290-320 nm.
“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]
The ‘UVB sunscreen compounds’ section reports cis–trans photoisomerization of the cinnamate after irradiation that included UVB at 290–320 nm, and assigns an additional chromatographic peak to the cis isomer. But the paper describes gas chromatography and mass spectrometry, not HPLC; its Figure 3 concerns a different compound. No page numbers are available in our copy. (LLM, conf=0.88)
Experimental — accuracy not yet measured4-MBC undergoes E-Z photoisomerisation but is considered stable due to similar UV spectra before and after irradiation and minimal change in photoprotective action.
“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]
Padimate O decomposes after irradiation forming two photoproducts, one from loss of a methyl group and another from oxidation of the amine group.
“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]
Padimate O is photoinstable for UVA and photostable for UVB radiation.
“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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BackgroundResultInfluentialPercutaneous absorption of benzophenone-3, a common component of topical sunscreens
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“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
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“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,…”
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“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].”
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“Maia Campos) UV-induced erythema and, as shown by many studies, their regular use prevents skin photodamage (2).”
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In vitro photostability and photoprotection studies of a novel ‘multi-active' UV-absorber
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“[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 38 · see citing works
“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 · see citing works
“The applied UVB energy corresponded to 20 Minimal Erythemal Doses, which is considered comparable with a daily solar emission [24].”
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Unexpected Photolysis of the Sunscreen Octinoxate in the Presence of the Sunscreen Avobenzone¶
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“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 · see citing works
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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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Variations in the Blaise Reaction: Conceptually New Synthesis of 3‐Amino Enones and 1,3‐Diketones
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Absorption and Photo-Stability of Substituted Dibenzoylmethanes and Chalcones as UVA Filters
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Solubilization of ultraviolet absorbers by cyclodextrin and their potential application in cosmetics
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Nanostructured Lipid Carriers (NLC) in dermal and personal care formulations
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Butyl Methoxy Dibenzoylmethane
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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).”
BackgroundHow the sun protection factor (SPF) of sunscreen films change during solar irradiation
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“Several studies have demonstrated that octyl methoxycinnamate (OMC) is unstable following irradiation both in solution([12]) and in emulsion formulations.”
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“[13].”
- 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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