{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,1]],"date-time":"2026-07-01T18:29:49Z","timestamp":1782930589214,"version":"3.54.5"},"reference-count":64,"publisher":"MDPI AG","issue":"13","license":[{"start":{"date-parts":[[2024,6,28]],"date-time":"2024-06-28T00:00:00Z","timestamp":1719532800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/100016247","name":"Wroc\u0142aw University of Environmental and Life Sciences (Poland)","doi-asserted-by":"publisher","award":["N090\/0005\/23"],"award-info":[{"award-number":["N090\/0005\/23"]}],"id":[{"id":"10.13039\/100016247","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["IJMS"],"abstract":"<jats:p>4\u2032-dihydrochalcones are secondary metabolites isolated from many medicinal plants and from the resin known as \u2018dragon\u2019s blood\u2019. Due to their biological potential, our research objective was to determine the possibilities of using biocatalysis processes carried out in deep eutectic solvents (DESs) to obtain 4\u2032-dihydrochalcones as a model compound. The processes were carried out in a culture of the yeast Yarrowia lipolytica KCh 71 and also in cultures of strains of the genera Rhodotorula and Debaryomyces. Based on the experiments carried out, an optimum process temperature of 35 \u00b0C was chosen, and the most suitable DES contained glycerol as a hydrogen bond donor (HBD). For a medium with 30% water content (DES 11), the conversion observed after 24 h exceeded 70%, while increasing the amount of water to 50% resulted in a similar level of conversion after just 1 h. A fivefold increase in the amount of added substrate resulted in a reduction in conversion, which reached 30.3%. Of the other yeast strains tested, Rhodotorula marina KCh 77 and Rhodotorula rubra KCh 4 also proved to be good biocatalysts for the bioreduction process. For these strains, the conversion reached 95.4% and 95.1%, respectively. These findings highlight the potential of yeast as a biocatalyst for the selective reduction of \u03b1,\u03b2-unsaturated ketones and the possibility of using a DESs as a reaction medium in this process.<\/jats:p>","DOI":"10.3390\/ijms25137152","type":"journal-article","created":{"date-parts":[[2024,7,2]],"date-time":"2024-07-02T12:58:42Z","timestamp":1719925122000},"page":"7152","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":12,"title":["Bioreduction of 4\u2032-Hydroxychalcone in Deep Eutectic Solvents: Optimization and Efficacy with Various Yeast Strains"],"prefix":"10.3390","volume":"25","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-6987-1096","authenticated-orcid":false,"given":"Pawe\u0142","family":"Chlipa\u0142a","sequence":"first","affiliation":[{"name":"Department of Food Chemistry and Biocatalysis, Wroc\u0142aw University of Environmental and Life Sciences, Norwida 25, 50-375 Wroc\u0142aw, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9757-6684","authenticated-orcid":false,"given":"Tomasz","family":"Janeczko","sequence":"additional","affiliation":[{"name":"Department of Food Chemistry and Biocatalysis, Wroc\u0142aw University of Environmental and Life Sciences, Norwida 25, 50-375 Wroc\u0142aw, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6192-5248","authenticated-orcid":false,"given":"Marcelina","family":"Mazur","sequence":"additional","affiliation":[{"name":"Department of Food Chemistry and Biocatalysis, Wroc\u0142aw University of Environmental and Life Sciences, Norwida 25, 50-375 Wroc\u0142aw, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2024,6,28]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"309","DOI":"10.1002\/elsc.200520089","article-title":"Highlights in biocatalysis\u2014Historical landmarks and current trends","volume":"5","author":"Bornscheuer","year":"2005","journal-title":"Eng. Life Sci."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"1105","DOI":"10.1021\/acscentsci.1c00273","article-title":"State-of-the-Art Biocatalysis","volume":"7","author":"Pyser","year":"2021","journal-title":"ACS Cent. Sci."},{"key":"ref_3","doi-asserted-by":"crossref","unstructured":"de Oliveira, N.S., da Silva, G.P.L., Furlan, O., Pe\u00f1a, L.C., Bianchini, L.F., Parahitiyawa, N., and Rosa, E.A.R. (2023). The song remains the same. The lab bench dilemma of using shaken flasks in microbial biotransformation experiments. Biocatal. Biotransformation, 1\u201326.","DOI":"10.1080\/10242422.2023.2284116"},{"key":"ref_4","doi-asserted-by":"crossref","unstructured":"Garz\u00f3n-Posse, F., Becerra-Figueroa, L., Hern\u00e1ndez-Arias, J., and Gamba-S\u00e1nchez, D. (2018). Whole Cells as Biocatalysts in Organic Transformations. Molecules, 23.","DOI":"10.3390\/molecules23061265"},{"key":"ref_5","doi-asserted-by":"crossref","unstructured":"Crnoglavac Popovi\u0107, M., Stani\u0161i\u0107, M., and Prodanovi\u0107, R. (2024). State of the Art Technologies for High Yield Heterologous Expression and Production of Oxidoreductase Enzymes: Glucose Oxidase, Cellobiose Dehydrogenase, Horseradish Peroxidase, and Laccases in Yeasts P. pastoris and S. cerevisiae. Fermentation, 10.","DOI":"10.3390\/fermentation10020093"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"9888","DOI":"10.1021\/acs.jafc.2c03306","article-title":"Screening and Remodeling of Enone Oxidoreductase for High Production of 2(or 5)-Ethyl-5(or 2)-methyl-4-hydroxy-3(2H)-Furanone in Saccharomyces Cerevisiae","volume":"70","author":"Fu","year":"2022","journal-title":"J. Agric. Food Chem."},{"key":"ref_7","doi-asserted-by":"crossref","unstructured":"de Gonzalo, G., and Alc\u00e1ntara, A.R. (2021). Multienzymatic Processes Involving Baeyer\u2013Villiger Monooxygenases. Catalysts, 11.","DOI":"10.3390\/catal11050605"},{"key":"ref_8","doi-asserted-by":"crossref","unstructured":"Zappaterra, F., Costa, S., Summa, D., Bertolasi, V., Semeraro, B., Pedrini, P., Buzzi, R., and Vertuani, S. (2021). Biotransformation of Cortisone with Rhodococcus rhodnii: Synthesis of New Steroids. Molecules, 26.","DOI":"10.3390\/molecules26051352"},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"253","DOI":"10.1007\/s10529-018-2631-3","article-title":"Green asymmetric reduction of acetophenone derivatives: Saccharomyces cerevisiae and aqueous natural deep eutectic solvent","volume":"41","author":"Roje","year":"2019","journal-title":"Biotechnol. Lett."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"1788","DOI":"10.1016\/j.procbio.2015.07.015","article-title":"Baker\u2019s yeast-mediated asymmetric reduction of ethyl 3-oxobutanoate in deep eutectic solvents","volume":"50","author":"Mazur","year":"2015","journal-title":"Process. Biochem."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"299","DOI":"10.3311\/PPch.17429","article-title":"Characterization of Yeast Strains with Ketoreductase Activity for Bioreduction of Ketones","volume":"65","author":"Csuka","year":"2021","journal-title":"Period. Polytech. Chem. Eng."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"111217","DOI":"10.1016\/j.mcat.2020.111217","article-title":"Biocatalytic reductive desymmetrization of prochiral 1,3-diketone and its application to microbial hormone synthesis","volume":"497","author":"Monna","year":"2020","journal-title":"Mol. Catal."},{"key":"ref_13","doi-asserted-by":"crossref","unstructured":"Stompor, M., Broda, D., and Bajek-Bil, A. (2019). Dihydrochalcones: Methods of Acquisition and Pharmacological Properties\u2014A First Systematic Review. Molecules, 24.","DOI":"10.3390\/molecules24244468"},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"393","DOI":"10.1080\/10242422.2022.2073226","article-title":"Biotransformation of chalcones and flavanones: An update on their bio-based derivatizations","volume":"40","author":"Aguiar","year":"2022","journal-title":"Biocatal. Biotransformation"},{"key":"ref_15","doi-asserted-by":"crossref","unstructured":"Krawczyk-\u0141ebek, A., Dymarska, M., Janeczko, T., and Kostrzewa-Sus\u0142ow, E. (2021). New Glycosylated Dihydrochalcones Obtained by Biotransformation of 2\u2032-Hydroxy-2-methylchalcone in Cultures of Entomopathogenic Filamentous Fungi. Int. J. Mol. Sci., 22.","DOI":"10.3390\/ijms22179619"},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"136","DOI":"10.1186\/s12934-017-0752-3","article-title":"Highly effective, regiospecific reduction of chalcone by cyanobacteria leads to the formation of dihydrochalcone: Two steps towards natural sweetness","volume":"16","author":"Lipok","year":"2017","journal-title":"Microb. Cell Fact."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"46","DOI":"10.1080\/10242422.2021.1956909","article-title":"Regioselective and chemoselective biotransformation of 2\u2032-hydroxychalcone derivatives by marine-derived fungi","volume":"41","author":"Nitschke","year":"2023","journal-title":"Biocatal. Biotransformation"},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"65","DOI":"10.1186\/s12934-024-02338-9","article-title":"Multienzymatic biotransformation of flavokawain B by entomopathogenic filamentous fungi: Structural modifications and pharmacological predictions","volume":"23","author":"Tronina","year":"2024","journal-title":"Microb. Cell Fact."},{"key":"ref_19","doi-asserted-by":"crossref","unstructured":"Krawczyk-\u0141ebek, A., Dymarska, M., Janeczko, T., and Kostrzewa-sus\u0142ow, E. (2022). Glycosylation of Methylflavonoids in the Cultures of Entomopathogenic Filamentous Fungi as a Tool for Obtaining New Biologically Active Compounds. Int. J. Mol. Sci., 23.","DOI":"10.3390\/ijms23105558"},{"key":"ref_20","doi-asserted-by":"crossref","unstructured":"Koz\u0142owska, J., Potaniec, B., and Anio\u0142, M. (2020). Biotransformation of Hydroxychalcones as a Method of Obtaining Novel and Unpredictable Products Using Whole Cells of Bacteria. Catalysts, 10.","DOI":"10.3390\/catal10101167"},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"8371","DOI":"10.1007\/s00253-016-7607-4","article-title":"Biotechnological methods for chalcone reduction using whole cells of Lactobacillus, Rhodococcus and Rhodotorula strains as a way to produce new derivatives","volume":"100","author":"Stompor","year":"2016","journal-title":"Appl. Microbiol. Biotechnol."},{"key":"ref_22","doi-asserted-by":"crossref","unstructured":"\u0141u\u017cny, M., Kaczanowska, D., Gawdzik, B., Wzorek, A., Pawlak, A., Obmi\u0144ska-Mrukowicz, B., Dymarska, M., Koz\u0142owska, E., Kostrzewa-Sus\u0142ow, E., and Janeczko, T. (2022). Regiospecific Hydrogenation of Bromochalcone by Unconventional Yeast Strains. Molecules, 27.","DOI":"10.3390\/molecules27123681"},{"key":"ref_23","doi-asserted-by":"crossref","unstructured":"\u0141u\u017cny, M., Koz\u0142owska, E., Kostrzewa-Sus\u0142ow, E., and Janeczko, T. (2020). Methoxychalcone by Yarrowia lipolytica Enables. Catalysts, 10.","DOI":"10.3390\/catal10101135"},{"key":"ref_24","doi-asserted-by":"crossref","unstructured":"Filippucci, S., Tasselli, G., Kenza Labbani, F.Z., Turchetti, B., Rita Cramarossa, M., Buzzini, P., and Forti, L. (2020). Non-conventional yeasts as sources of ene-reductases for the bioreduction of chalcones. Fermentation, 6.","DOI":"10.3390\/fermentation6010029"},{"key":"ref_25","doi-asserted-by":"crossref","unstructured":"Zieniuk, B., Jasi\u0144ska, K., Wierzchowska, K., U\u011fur, \u015e., and Fabiszewska, A. (2024). Yarrowia lipolytica Yeast: A Treasure Trove of Enzymes for Biocatalytic Applications\u2014A Review. Fermentation, 10.","DOI":"10.3390\/fermentation10050263"},{"key":"ref_26","first-page":"e05594","article-title":"Safety of Yarrowia lipolytica yeast biomass as a novel food pursuant to Regulation (EU) 2015\/2283","volume":"17","author":"Turck","year":"2019","journal-title":"EFSA J."},{"key":"ref_27","first-page":"e07450","article-title":"Safety of an extension of use of Yarrowia lipolytica yeast biomass as a novel food pursuant to Regulation (EU) 2015\/2283","volume":"20","author":"Turck","year":"2022","journal-title":"EFSA J."},{"key":"ref_28","doi-asserted-by":"crossref","unstructured":"\u0141uzny, M., Krzywda, M., Koz\u0142owska, E., Kostrzewa-Sus\u0142ow, E., and Janeczko, T. (2019). Effective Hydrogenation of 3-(2\u201d-furyl)- And 3-(2\u201d-thienyl)-1-(2\u2032-hydroxyphenyl)-prop-2-en-1-one in Selected Yeast Cultures. Molecules, 24.","DOI":"10.3390\/molecules24173185"},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"27","DOI":"10.1016\/j.cogsc.2019.09.004","article-title":"Deep eutectic solvents and their applications as green solvents","volume":"21","author":"Perna","year":"2020","journal-title":"Curr. Opin. Green Sustain. Chem."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"361","DOI":"10.1186\/1472-6882-11-13","article-title":"Bioprotective properties of Dragon\u2019s blood resin: In vitro evaluation of antioxidant activity and antimicrobial activity","volume":"11","author":"Gupta","year":"2011","journal-title":"BMC Complement. Altern. Med."},{"key":"ref_31","doi-asserted-by":"crossref","unstructured":"Al-Awthan, Y.S., and Bahattab, O.S. (2021). Phytochemistry and Pharmacological Activities of Dracaena cinnabari Resin. Biomed. Res. Int., 2021.","DOI":"10.1155\/2021\/8561696"},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"1046","DOI":"10.1111\/jocd.15515","article-title":"Enhanced intradermal delivery of Dragon\u2019s blood in biocompatible nanosuspensions hydrogel patch for skin photoprotective effect","volume":"22","author":"Wang","year":"2022","journal-title":"J. Cosmet. Dermatol."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"14795","DOI":"10.1038\/s41598-022-18913-2","article-title":"Lipase-mediated Baeyer-Villiger oxidation of benzylcyclopentanones in ester solvents and deep eutectic solvents","volume":"12","author":"Mazur","year":"2022","journal-title":"Sci. Rep."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"117196","DOI":"10.1016\/j.seppur.2020.117196","article-title":"Simple and green method for the extraction of xanthohumol from spent hops using deep eutectic solvents","volume":"250","author":"Grudniewska","year":"2020","journal-title":"Sep. Purif. Technol."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"582","DOI":"10.1039\/D0RE00458H","article-title":"Deep eutectic solvents: Alternative reaction media for organic oxidation reactions","volume":"6","author":"Abbott","year":"2021","journal-title":"React. Chem. Eng."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"943","DOI":"10.1016\/j.tibtech.2019.03.007","article-title":"Deep Eutectic Solvents as Efficient Solvents in Biocatalysis","volume":"37","author":"Siebenhaller","year":"2019","journal-title":"Trends Biotechnol."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"1063","DOI":"10.1021\/sc500096j","article-title":"Natural deep eutectic solvents\u2014Solvents for the 21st century","volume":"2","author":"Paiva","year":"2014","journal-title":"ACS Sustain. Chem. Eng."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"100654","DOI":"10.1016\/j.scp.2022.100654","article-title":"Natural deep eutectic solvents improve the solubility of acetylcholinesterase reactivator RS194B","volume":"27","author":"Hrvat","year":"2022","journal-title":"Sustain. Chem. Pharm."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"5713","DOI":"10.1021\/acssuschemeng.7b00285","article-title":"Improving Whole-Cell Biocatalysis by Addition of Deep Eutectic Solvents and Natural Deep Eutectic Solvents","volume":"5","author":"Yang","year":"2017","journal-title":"ACS Sustain. Chem. Eng."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"14212","DOI":"10.1021\/acs.jafc.0c04964","article-title":"Optimization of Culture Conditions for the Efficient Biosynthesis of Trilobatin from Phloretin by Engineered Escherichia coli Harboring the Apple Phloretin-4\u2032-O-glycosyltransferase","volume":"68","author":"Nawade","year":"2020","journal-title":"J. Agric. Food Chem."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"1014","DOI":"10.1021\/jm970432t","article-title":"Cytotoxic activities of Mannich bases of chalcones and related compounds","volume":"41","author":"Dimmock","year":"1998","journal-title":"J. Med. Chem."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"33","DOI":"10.1016\/S0014-5793(03)01398-X","article-title":"Chalcone dimethylallyltransferase from Morus nigra cell cultures. Substrate specificity studies","volume":"557","author":"Vitali","year":"2004","journal-title":"FEBS Lett."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"553","DOI":"10.1021\/np030448o","article-title":"Microbial Transformations of Chalcones: Hydroxylation, O -Demethylation, and Cyclization to Flavanones","volume":"67","author":"Rosazza","year":"2004","journal-title":"J. Nat. Prod."},{"key":"ref_44","doi-asserted-by":"crossref","unstructured":"Lewis, J.A., Jacobo, E.P., Palmer, N., Vermerris, W., Sattler, S.E., Brozik, J.A., Sarath, G., and Kang, C. (2024). Structural and Interactional Analysis of the Flavonoid Pathway Proteins: Chalcone Synthase, Chalcone Isomerase and Chalcone Isomerase-like Protein. Int. J. Mol. Sci., 25.","DOI":"10.3390\/ijms25115651"},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"398","DOI":"10.1021\/acs.jnatprod.2c01027","article-title":"Identification and Functional Characterization of Fungal Chalcone Synthase and Chalcone Isomerase","volume":"86","author":"Furumura","year":"2023","journal-title":"J. Nat. Prod."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"27","DOI":"10.3390\/molecules27072300","article-title":"Yarrowia lipolytica as an Alternative and Valuable Source of Nutritional and Bioactive Compounds for Humans","volume":"27","author":"Jach","year":"2022","journal-title":"Molecules"},{"key":"ref_47","doi-asserted-by":"crossref","unstructured":"L\u00f3pez-Trujillo, J., Mellado-Bosque, M., Ascacio-Vald\u00e9s, J.A., Prado-Barrag\u00e1n, L.A., Hern\u00e1ndez-Herrera, J.A., and Aguilera-Carb\u00f3, A.F. (2023). Temperature and pH Optimization for Protease Production Fermented by Yarrowia lipolytica from Agro-Industrial Waste. Fermentation, 9.","DOI":"10.3390\/fermentation9090819"},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"9914","DOI":"10.1002\/ange.201702486","article-title":"The Effect of Water upon Deep Eutectic Solvent Nanostructure: An Unusual Transition from Ionic Mixture to Aqueous Solution","volume":"129","author":"Hammond","year":"2017","journal-title":"Angew. Chem."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"111301","DOI":"10.1016\/j.molliq.2019.111301","article-title":"Effect of water addition on choline chloride\/glycol deep eutectic solvents: Characterization of their structural and physicochemical properties","volume":"291","author":"Gabriele","year":"2019","journal-title":"J. Mol. Liq."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"2221","DOI":"10.1021\/je5001796","article-title":"Densities and viscosities of (choline chloride + urea) deep eutectic solvent and its aqueous mixtures in the temperature range 293.15 K to 363.15 K","volume":"59","author":"Yadav","year":"2014","journal-title":"J. Chem. Eng. Data"},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"159","DOI":"10.1016\/j.jct.2018.09.029","article-title":"Physical properties of aqueous mixtures of (choline chloride + glucose) deep eutectic solvents","volume":"129","author":"Moghimi","year":"2019","journal-title":"J. Chem. Thermodyn."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"17565","DOI":"10.1021\/acssuschemeng.9b05096","article-title":"Looking at the \u201cwater-in-Deep-Eutectic-Solvent\u201d System: A Dilution Range for High Performance Eutectics","volume":"7","author":"Imberti","year":"2019","journal-title":"ACS Sustain. Chem. Eng."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"55","DOI":"10.1016\/j.molcatb.2013.09.021","article-title":"Microbial transformations of chalcones to produce food sweetener derivatives","volume":"98","author":"Janeczko","year":"2013","journal-title":"J. Mol. Catal. B Enzym."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"4090","DOI":"10.1021\/ja01165a069","article-title":"cis-Benzalacetophenone","volume":"72","author":"Lutz","year":"1950","journal-title":"J. Am. Chem. Soc."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"1266","DOI":"10.1248\/bpb.20.1266","article-title":"Antitumorigenic activity of chalcones (II). Photo-isomerization of chalcones and correlation with their biological activities","volume":"20","author":"Iwata","year":"1997","journal-title":"Biol. Pharm. Bull."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"1509","DOI":"10.1016\/0040-4020(77)88013-7","article-title":"Conformational study on some \u03b2-phenyl-\u03b1,\u03b2-unsaturated ketones","volume":"33","author":"Baas","year":"1977","journal-title":"Tetrahedron"},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"185","DOI":"10.1016\/j.jphotochem.2004.05.022","article-title":"Thermal and photochemical properties of 4\u2032-hydroxyflavylium in water-ionic liquid biphasic systems","volume":"168","author":"Fernandez","year":"2004","journal-title":"J. Photochem. Photobiol. A Chem."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"2766","DOI":"10.1021\/jp0133081","article-title":"Photochemistry of 2\u2032-hydroxychalcone. One-way cis-trans photoisomerization induced by adiabatic intramolecular hydrogen atom transfer","volume":"106","author":"Norikane","year":"2002","journal-title":"J. Phys. Chem. A"},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"1094","DOI":"10.1246\/cl.2000.1094","article-title":"Control of the photoisomerization mode of carbon-carbon double bond by intramolecular hydrogen bond; one-way photoisomerization of 2\u2032-hydroxychalcone induced by adiabatic intramolecular hydrogen atom transfer","volume":"1","author":"Norikane","year":"2000","journal-title":"Chem. Lett."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"743","DOI":"10.1039\/P29850000743","article-title":"Photochemical cyclization of 2\u2032-hydroxychalcones","volume":"2","author":"Matsushima","year":"1985","journal-title":"J. Chem. Soc. Perkin Trans."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"381","DOI":"10.1039\/b612612j","article-title":"Substitution and solvent effects in the chalcones isomerization barrier of flavylium photochromic systems","volume":"6","author":"Roque","year":"2007","journal-title":"Photochem. Photobiol. Sci."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"8924","DOI":"10.1039\/C8CP00602D","article-title":"Impacts of hydroxylation on the photophysics of chalcones: Insights into the relation between the chemical composition and the electronic structure","volume":"20","author":"Kalchevski","year":"2018","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"1184","DOI":"10.1002\/(SICI)1521-3765(19980710)4:7<1184::AID-CHEM1184>3.0.CO;2-6","article-title":"Multistate\/multifunctional molecular-level systems: Light and pH switching between the various forms of a synthetic flavylium salt","volume":"4","author":"Pina","year":"1998","journal-title":"Chem. A Eur. J."},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"1149","DOI":"10.4028\/www.scientific.net\/AMR.1033-1034.1149","article-title":"Light induced properties of chalcones correlated with molecular structure and photophysical properties for permanent optical storage device","volume":"1033\u20131034","author":"Sidharth","year":"2014","journal-title":"Adv. Mater. Res."}],"container-title":["International Journal of Molecular Sciences"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1422-0067\/25\/13\/7152\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T15:07:22Z","timestamp":1760108842000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1422-0067\/25\/13\/7152"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,6,28]]},"references-count":64,"journal-issue":{"issue":"13","published-online":{"date-parts":[[2024,7]]}},"alternative-id":["ijms25137152"],"URL":"https:\/\/doi.org\/10.3390\/ijms25137152","relation":{},"ISSN":["1422-0067"],"issn-type":[{"value":"1422-0067","type":"electronic"}],"subject":[],"published":{"date-parts":[[2024,6,28]]}}}