Chlorination of UV filters with antioxidant shield in swimming pool waters - products identification and toxicity assessment

Bavcon Kralj, Mojca (author), Lebedev, Albert T. (author), Trebše, Polonca (author)

This work summarizes our research on synthesis, characterization and toxicity of selected UV-A filters and their antioxidant shield in commercial formulation – resveratrol. Benzophenone type of UV filters react under disinfection conditions with chlorine and form different mono- and dichlorinated products, while dibenzoylmethane derivatives, such as avobenzone, react with chlorine and form two main bridge chlorinated products followed by numerous chlorinated species at the advanced stages of the process. Resveratrol showed three main susceptible centers to chlorination, start¬ing from the electrophilic addition to the double bond and continuing with the chlorination of the phenolic moieties. Several experiments conducted under different disinfection conditions (pool/sea water, addition of salts, irradiation) showed basically similar chlorination patterns with some variations in terms of product formation. The results of toxicity assessment using different test organisms (Vibrio fischeri, microalgae, daphnids) have shown different sensitivity of testing organisms to the parent UV filters in comparison with chlorinated products as well as different toxicity for specific UV filter in comparison to the others. As the closing loop of all experiments in the laboratory, an up-scaling to the real human skin is presented.

• Language: English
• Keywords: UV filtri, kloriranje, stranski produkti dezinfekcije, strupenost
• Work type: Article
• Typology: 1.02 - Review Article
• Organization: ZF - Faculty of Health Sciences
• Publication status: Published
• Publication version: Version of Record
• Publication date: 20.12.2023
• Year: 2023
• Number of pages: Str. 601-610
• Numbering: Vol. 70, no. 4
• PID: 20.500.12556/RUL-153309
• UDC: 543:628.166.094.413
• ISSN on article: 1580-3155
• DOI: 10.17344/acsi.2023.8411
• COBISS.SI-ID: 178436099
• Publication date in RUL: 21.12.2023

Record is a part of a journal

• Title: Acta chimica slovenica
• Shortened title: Acta chim. slov.
• Publisher: Slovensko kemijsko društvo, =Slovenian Chemical Society
• ISSN: 1580-3155
• COBISS.SI-ID: 21870085

Licences

• License: CC BY 4.0, Creative Commons Attribution 4.0 International
• Link: http://creativecommons.org/licenses/by/4.0/
• Description: This is the standard Creative Commons license that gives others maximum freedom to do what they want with the work as long as they credit the author.

Secondary language

• Language: Slovenian

Abstract

Članek povzema raziskave naše skupine o sintezi, karakterizaciji in toksičnosti izbranih UV-A filtrov in ter vlogo an-tioksidanta resveratrola kot dodatka v kremah za zaščito pred soncem. UV filtri benzofenonskega tipa reagirajo pod dezinfekcijskimi pogoji s klorom, pri čemer se tvorijo mono- in diklorirani produkti. Derivati dibenzoilmetana, kot je avobenzon, pa reagirajo s klorom tako, da najprej reagira metilenska skupina avobenzona, pri čemer se tvorita dva glavna klorirana produkta, v nadaljevanju procesa pa sledi nastanek številnih kloriranih produktov. Resveratrol vsebuje tri skupine, na katerih poteče kloriranje, začenši z elektrofilno adicijo na dvojno vez ter s kloriranjem fenolnih delov. Več poskusov, izvedenih v različnih pogojih dezinfekcije (bazen/morska voda, dodajanje soli, obsevanje s svetlobo), je pokazalo podobne vzorce kloriranja z razlikami pri številu in tipu produktov. Rezultati ugotavljanja toksičnosti z uporabo različnih testnih organizmov (Vibrio fischeri, mikroalge, vodne bolhe) so pokazali različno občutljivost testnih organizmov na osnovne UV filtre v primerjavi s kloriranimi produkti ter različno toksičnost posameznih UV filtrov. Nadgradnjo vseh laboratorijskih poskusov predstavlja študija izpostavljenosti pogojem kloriranja in obsevanja, ki je bila izvedena na človeški koži.

• Keywords: UV filters, chlorination, disinfection by-products, toxicity

Projects

• Funder: ARRS - Slovenian Research Agency
• Funding programme: Javna agencija za znanstvenoraziskovalno in inovacijsko dejavnost Republike Slovenije
• Project number: P3-0388
• Name: Mehanizmi varovanja zdravja