A blocked diketo form of avobenzone: Photostability, photosensitizing properties and triplet quenching by a triazine-derived UVB-filter
Open accessAbstract
Novel sunscreens are required providing active protection in the UVA and UVB regions. On the other hand, there is an increasing concern about the photosafety of UV filters, as some of them are not sufficiently photostable. Avobenzone is one of the most frequently employed sunscreen ingredients, but it has been reported to partially decompose after irradiation. In the present work, photophysical and photochemical studies on a methylated avobenzone‐derivative have shown that the diketo form is responsible for photodegradation. A transient absorption was observed at 380 nm after laser flash photolysis excitation at 308 nm. It was assigned to the triplet excited state of the diketo form, as inferred from quenching by oxygen and β‐carotene. This transient also interacted with key building blocks of biomolecules by triplet–triplet energy transfer (in the case of thymidine) or electron transfer processes (for 2′‐deoxyguanosine, tryptophan and tyrosine). Irradiation of the avobenzone derivative in the presence of a triazine UV‐B filter (E‐35852) diminished the undesirable effects of the compound by an efficient quenching of the triplet excited state. Thus, sunscreen formulations including triplet quenchers could provide effective protection from the potential phototoxic and photoallergic effects derived from poor photostability of avobenzone.
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A methylated derivative of avobenzone blocking keto-enol conversion plus a triazine triplet quencher reduces undesirable effects by quenching the triplet excited state.
“For instance, Paris et al. (2019) prepared a methylated derivative of avobenzone (11) in order to block the conversion between keto-enol forms, and a new triazine triplet quencher molecule was added, reducing the undesirable effects of the UV filter by successful quenching the triplet excited state of UV filter [39].”
From UV Filters: Challenges and Prospects (2022) · cites this paper as [39]
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Efficient ultraviolet-light energy dissipation by an aromatic ketone.
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Sahoo, D. K., More, S., & Gowd, K. H. (2025) · Journal of Sulfur Chemistry · doi:10.1080/17415993.2025.2571657
“…independent approaches have been employed to overcome the draw-back of photounstability of avobenzone: (i) the addition of photostabilizers, [9–12] (ii) structural modifications to improve intrinsic photostability, [13–16] and (iii) encapsulation for slow and sustained release into the system.”
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- Authors
- Paris, C., Lhiaubet‐Vallet, V., Jiménez, O., Trullas, C., & Miranda, M. Á.
- Affiliations
- Consejo Superior de Investigaciones Científicas (ES)
- Venue
- Photochemistry and Photobiology
- Publisher
- Wiley
- Published
- 2009-01
- Volume
- 85
- Issue
- 1
- Pages
- 178-184
- ISSN
- 0031-8655 (ISSN-L)
- 1751-1097
- OpenAlex
- W2089303504
- Cited by
- 112
- References
- 0
- Citations by year
- 2025: 6 · 2024: 3 · 2023: 8 · 2022: 5 · 2021: 9 · 2020: 9 · 2019: 6 · 2018: 9 · 2017: 6 · 2016: 8 · 2015: 9 · 2014: 8 · 2013: 7 · 2012: 7
- FWCI
- 4.27
- Type
- journal article
- Language
- en
- Open access
- bronze
- doi.org
- Locations
- Photochemistry and Photobiology (publishedVersion)
- PubMed (publishedVersion)
- Topics
- Health Sciences › Medicine › Dermatology › Skin Protection and Aging
- Physical Sciences › Chemistry › Physical and Theoretical Chemistry › Photochemistry and Electron Transfer Studies
- Physical Sciences › Materials Science › Materials Chemistry › Photochromic and Fluorescence Chemistry
- Keywords
- avobenzone, photostability, photodegradation, triplet state, triplet quenching, sunscreen ingredients, photosensitization, triplet-triplet energy transfer, electron transfer, thymidine, 2'-deoxyguanosine, tryptophan, tyrosine, phototoxicity, photoallergy, transient absorption spectroscopy
- MeSH terms
- Ketoses, Methylation, Propiophenones, Ultraviolet Rays, Molecular Structure, Photosensitizing Agents, Singlet Oxygen, Chalcones, Photochemical Processes
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