Evidence map›Paper›PMID 39772649›Full record

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.

Chihiro Kuroda, Tomohiro Tsuchida, Chihiro Tsunoda, Megumi Minamide, Ryosuke Hiroshige, Satoru Goto

Abstract read
In one paragraph

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.

0numbers the graph read from it
0cells of the map it votes in
6citing papers in PubMed
–field-weighted citation impact
1 · What the graph read from it

What it found

Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.

The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.

2 · The registry

The trial behind it

Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.

Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.

3 · Its place in the literature

Who cites it

6 citing papers in PubMed.

  1. Article
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4 · The record

Corrections and comments

PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.

5 · Who and what money

Authors and funding

6 authors.

Chihiro KurodaFaculty of Pharmaceutical Sciences, Tokyo University of Science, 2641 Yamazaki, Noda, Chiba 278-8510, Japan.
Tomohiro TsuchidaFaculty of Pharmaceutical Sciences, Tokyo University of Science, 2641 Yamazaki, Noda, Chiba 278-8510, Japan.ORCID 0000-0001-9024-9210
Chihiro TsunodaFaculty of Pharmaceutical Sciences, Tokyo University of Science, 2641 Yamazaki, Noda, Chiba 278-8510, Japan.
Megumi MinamideFaculty of Pharmaceutical Sciences, Tokyo University of Science, 2641 Yamazaki, Noda, Chiba 278-8510, Japan.
Ryosuke HiroshigeFaculty of Pharmaceutical Sciences, Tokyo University of Science, 2641 Yamazaki, Noda, Chiba 278-8510, Japan.
Satoru GotoFaculty of Pharmaceutical Sciences, Tokyo University of Science, 2641 Yamazaki, Noda, Chiba 278-8510, Japan.ORCID 0000-0001-8088-9070

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

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.

Indexed as

Benzophenonesbeta-CyclodextrinsPropiophenonesSunscreening AgentsUltraviolet RaysCurcuminIsomerismSolubilityWateravobenzoneBenzophenonesbeta-CyclodextrinsbetadexCurcuminoxybenzonePropiophenonesSunscreening AgentsWater

Identifiers

PMID39772649
PMCPMC11755785

What Socratic holds

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LicenceCC BY
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Registered trials

None linked

Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the Socratic graph.