{"title":"Pyrimidine derivative mimicking the locked enol form of avobenzone acts as a photostable UVAII and UVB filter","authors":"Deepak Kumar Sahoo , Abhishek Nayak , Srinivas Reddy Dannarm , A. Subha Jahnavi , Amol G. Dikundwar , Rajesh Sonti , Konkallu Hanumae Gowd","doi":"10.1016/j.jphotochem.2024.116099","DOIUrl":null,"url":null,"abstract":"<div><div>The broad UVA (UVAI and UVAII) filtering activity of the sunscreen agent avobenzone is due to its enolic forms which undergoes ketonization followed by degradation upon exposure to sunlight/radiation. The current report aims to lock the enolic forms of avobenzone through chemical derivatization that preserves the chelated intramolecular hydrogen bond geometry. The pyrimidine derivative mimicking both the enol-1 and enol-2 forms of avobenzone has been synthesized and evaluated for it photostability under natural sunlight by UV spectroscopy. The avobenzone pyrimidine derivative acts as a broad-spectrum UVAII, and UVB filter and exhibits unprecedented photostability under sunlight. The new derivative of avobenzone is a valuable additive to the tool kit of chemical UV filters and its poor skin permeability relative to the native avobenzone may be an advantage for cosmetics.</div></div>","PeriodicalId":16782,"journal":{"name":"Journal of Photochemistry and Photobiology A-chemistry","volume":null,"pages":null},"PeriodicalIF":4.1000,"publicationDate":"2024-10-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Photochemistry and Photobiology A-chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S1010603024006439","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, PHYSICAL","Score":null,"Total":0}
引用次数: 0
Abstract
The broad UVA (UVAI and UVAII) filtering activity of the sunscreen agent avobenzone is due to its enolic forms which undergoes ketonization followed by degradation upon exposure to sunlight/radiation. The current report aims to lock the enolic forms of avobenzone through chemical derivatization that preserves the chelated intramolecular hydrogen bond geometry. The pyrimidine derivative mimicking both the enol-1 and enol-2 forms of avobenzone has been synthesized and evaluated for it photostability under natural sunlight by UV spectroscopy. The avobenzone pyrimidine derivative acts as a broad-spectrum UVAII, and UVB filter and exhibits unprecedented photostability under sunlight. The new derivative of avobenzone is a valuable additive to the tool kit of chemical UV filters and its poor skin permeability relative to the native avobenzone may be an advantage for cosmetics.
期刊介绍:
JPPA publishes the results of fundamental studies on all aspects of chemical phenomena induced by interactions between light and molecules/matter of all kinds.
All systems capable of being described at the molecular or integrated multimolecular level are appropriate for the journal. This includes all molecular chemical species as well as biomolecular, supramolecular, polymer and other macromolecular systems, as well as solid state photochemistry. In addition, the journal publishes studies of semiconductor and other photoactive organic and inorganic materials, photocatalysis (organic, inorganic, supramolecular and superconductor).
The scope includes condensed and gas phase photochemistry, as well as synchrotron radiation chemistry. A broad range of processes and techniques in photochemistry are covered such as light induced energy, electron and proton transfer; nonlinear photochemical behavior; mechanistic investigation of photochemical reactions and identification of the products of photochemical reactions; quantum yield determinations and measurements of rate constants for primary and secondary photochemical processes; steady-state and time-resolved emission, ultrafast spectroscopic methods, single molecule spectroscopy, time resolved X-ray diffraction, luminescence microscopy, and scattering spectroscopy applied to photochemistry. Papers in emerging and applied areas such as luminescent sensors, electroluminescence, solar energy conversion, atmospheric photochemistry, environmental remediation, and related photocatalytic chemistry are also welcome.