ArticleLangmuir : the ACS journal of surfaces and colloids2025
Stability and Properties of Ultraviolet Filter Avobenzone under Its Diketo/Enol Tautomerization Induced by Molecular Encapsulation with β-Cyclodextrin.
Article in Langmuir : the ACS journal of surfaces and colloids, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed.
- Multifunctional System with Ferulic Acid: Increased Safety, Antioxidant Activity, and Efficacy of Sunscreen Formulations.Antioxidants (Basel, Switzerland) · 2026Article
- Cyclodextrin-Based Delivery Systems in Cosmeceuticals: Current Advances and Future Perspectives.Biomolecules · 2026Review
- Disrupting the Photochemical Landscape of a β-Diketone via Electrostatic Perturbation of Ground-State Tautomers.Journal of the American Chemical Society · 2025Article
- Comparative Study of UVA Filtering Compounds 2‑Methyl/2-Amino Pyrimidine Derivatives of Avobenzone under Acidic Conditions.ACS omega · 2025Article
- Potential of pyridine nanobelt in detecting and trapping of harmful UV filters.Scientific reports · 2025Article
- Computed libraries of avobenzone derivatives with sulfur groups as enhanced UVA filters.Journal of molecular modeling · 2025Article
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Authors and funding
6 authors.
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Abstract
Inclusion complexation of the sunscreen ingredient avobenzone (AVB) with β-cyclodextrin (β-CD) was investigated to improve its aqueous solubility and photostability; another ultraviolet (UV) filter, oxybenzone (OXB), and the phytochemical antioxidant curcumin (CUR) served as a comparison. In this study, the 1-octanol/water partition coefficients, acid dissociation constants, phase-solubility diagrams with β-CD, and ultraviolet-visible (UV-vis) spectral changes induced by UVA1 (365 nm) irradiation were evaluated. β-CD at concentrations 50-100 times that of AVB most effectively protected the photostability of AVB. Additionally, an UVA1-insensitive species with a diketo tautomer, which has an UVC-absorbing band and the potential to cause photodegradation, was stored in the inclusion complex. Acetonitrile-water mixtures at various volume ratios were screened to mimic the internal cavity of β-CD for the AVB tautomeric species using nuclear magnetic resonance (NMR) spectral integrals for the components. The results indicated that β-CD provides a hydrophobic environment similar to that of a 40-50% acetonitrile aqueous solution and enhances the photostability of AVB. However, excess β-CD induced a hyperchromic effect on the diketo tautomer. Aggregation of the AVB/β-CD inclusion complexes at β-CD concentrations of ≥2 mM enhances UVC band absorption. To avoid excess β-CD, a molar ratio of 50-100 of β-CD to AVB is recommended as the optimal composition. This study newly exhibited that the cavity of β-CD mitigates the reactivity of UVA1 toward AVB by inducing the diketo tautomer form of AVB within the cavity.
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