{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,25]],"date-time":"2026-03-25T22:02:03Z","timestamp":1774476123252,"version":"3.50.1"},"reference-count":50,"publisher":"MDPI AG","issue":"9","license":[{"start":{"date-parts":[[2022,4,20]],"date-time":"2022-04-20T00:00:00Z","timestamp":1650412800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001871","name":"Funda\u00e7\u00e3o para a Ci\u00eancia e Tecnologia","doi-asserted-by":"publisher","award":["project CICECO-Aveiro Institute of Materials, UIDB\/50011\/2020, UIDP\/50011\/2020 and LA\/P\/0006\/2020, and project CIMO-Mountain Research Center, UIDB\/00690\/2020 and LA\/P\/0007\/2020"],"award-info":[{"award-number":["project CICECO-Aveiro Institute of Materials, UIDB\/50011\/2020, UIDP\/50011\/2020 and LA\/P\/0006\/2020, and project CIMO-Mountain Research Center, UIDB\/00690\/2020 and LA\/P\/0007\/2020"]}],"id":[{"id":"10.13039\/501100001871","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001871","name":"Funda\u00e7\u00e3o para a Ci\u00eancia e Tecnologia","doi-asserted-by":"publisher","award":["AllNat - POCI-01-0145-FEDER-030463 (PTDC\/EQU-EPQ\/30463\/2017)"],"award-info":[{"award-number":["AllNat - POCI-01-0145-FEDER-030463 (PTDC\/EQU-EPQ\/30463\/2017)"]}],"id":[{"id":"10.13039\/501100001871","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001871","name":"Funda\u00e7\u00e3o para a Ci\u00eancia e Tecnologia","doi-asserted-by":"publisher","award":["funded by national funds through the FCT\/MCTES (PIDDAC)) to CIQUP, Faculty of Science, University of Porto (Project UIDB\/00081\/2020), IMS-Institute of Molecular Sciences (LA\/P\/0056\/2020)"],"award-info":[{"award-number":["funded by national funds through the FCT\/MCTES (PIDDAC)) to CIQUP, Faculty of Science, University of Porto (Project UIDB\/00081\/2020), IMS-Institute of Molecular Sciences (LA\/P\/0056\/2020)"]}],"id":[{"id":"10.13039\/501100001871","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001871","name":"Funda\u00e7\u00e3o para a Ci\u00eancia e Tecnologia","doi-asserted-by":"publisher","award":["PhD grant (UI\/BD\/151114\/2021);"],"award-info":[{"award-number":["PhD grant (UI\/BD\/151114\/2021);"]}],"id":[{"id":"10.13039\/501100001871","id-type":"DOI","asserted-by":"publisher"}]},{"name":"FEDER funds through COMPETE2020","award":["AllNat - POCI-01-0145-FEDER-030463 (PTDC\/EQU-EPQ\/30463\/2017)"],"award-info":[{"award-number":["AllNat - POCI-01-0145-FEDER-030463 (PTDC\/EQU-EPQ\/30463\/2017)"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>The formation of deep eutectic solvents (DES) is tied to negative deviations to ideality caused by the establishment of stronger interactions in the mixture than in the pure DES precursors. This work tested thymol and menthol as hydrogen bond donors when combined with different flavonoids. Negative deviations from ideality were observed upon mixing thymol with either flavone or flavanone, two parent flavonoids that only have hydrogen bond acceptor (HBA) groups, thus forming non-ionic DES (Type V). On the other hand, the menthol systems with the same compounds generally showed positive deviations from ideality. That was also the case with the mixtures containing the more complex hydroxylated flavonoid, hesperetin, which resulted in positive deviations when mixed with either thymol or menthol. COSMO-RS successfully predicted the behavior of the solid-liquid phase diagram of the studied systems, allowing for evaluation of the impact of the different contributions to the intermolecular interactions, and proving to be a good tool for the design of DES.<\/jats:p>","DOI":"10.3390\/molecules27092649","type":"journal-article","created":{"date-parts":[[2022,4,21]],"date-time":"2022-04-21T03:46:11Z","timestamp":1650512771000},"page":"2649","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":19,"title":["Liquefying Flavonoids with Terpenoids through Deep Eutectic Solvent Formation"],"prefix":"10.3390","volume":"27","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-5213-5359","authenticated-orcid":false,"given":"Gabriel","family":"Teixeira","sequence":"first","affiliation":[{"name":"CICECO-Aveiro Institute of Materials, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0097-2072","authenticated-orcid":false,"given":"Dinis O.","family":"Abranches","sequence":"additional","affiliation":[{"name":"CICECO-Aveiro Institute of Materials, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6636-1920","authenticated-orcid":false,"given":"Liliana P.","family":"Silva","sequence":"additional","affiliation":[{"name":"CICECO-Aveiro Institute of Materials, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8179-935X","authenticated-orcid":false,"given":"S\u00e9rgio M.","family":"Vilas-Boas","sequence":"additional","affiliation":[{"name":"CICECO-Aveiro Institute of Materials, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal"},{"name":"Mountain Research Center (CIMO), Polytechnic Institute of Bragan\u00e7a, Campus de Santa Apol\u00f3nia, 5300-253 Bragan\u00e7a, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9211-857X","authenticated-orcid":false,"given":"Sim\u00e3o P.","family":"Pinho","sequence":"additional","affiliation":[{"name":"Mountain Research Center (CIMO), Polytechnic Institute of Bragan\u00e7a, Campus de Santa Apol\u00f3nia, 5300-253 Bragan\u00e7a, Portugal"}]},{"given":"Ana I. M. C. L.","family":"Ferreira","sequence":"additional","affiliation":[{"name":"CIQUP, Institute of Molecular Sciences (IMS)\u2014Departamento de Qu\u00edmica e Bioqu\u00edmica, Faculdade de Ci\u00eancias da Universidade do Porto, Rua Campo Alegre, 4169-007 Porto, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3040-0358","authenticated-orcid":false,"given":"Lu\u00eds M. N. B. F.","family":"Santos","sequence":"additional","affiliation":[{"name":"CIQUP, Institute of Molecular Sciences (IMS)\u2014Departamento de Qu\u00edmica e Bioqu\u00edmica, Faculdade de Ci\u00eancias da Universidade do Porto, Rua Campo Alegre, 4169-007 Porto, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8414-3479","authenticated-orcid":false,"given":"Olga","family":"Ferreira","sequence":"additional","affiliation":[{"name":"Mountain Research Center (CIMO), Polytechnic Institute of Bragan\u00e7a, Campus de Santa Apol\u00f3nia, 5300-253 Bragan\u00e7a, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3841-743X","authenticated-orcid":false,"given":"Jo\u00e3o A. P.","family":"Coutinho","sequence":"additional","affiliation":[{"name":"CICECO-Aveiro Institute of Materials, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal"}]}],"member":"1968","published-online":{"date-parts":[[2022,4,20]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"301","DOI":"10.1039\/B918763B","article-title":"Green Chemistry: Principles and Practice","volume":"39","author":"Anastas","year":"2010","journal-title":"Chem. Soc. Rev."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"878","DOI":"10.1021\/acs.jafc.0c06641","article-title":"Review on Extraction of Phenolic Compounds from Natural Sources Using Green Deep Eutectic Solvents","volume":"69","year":"2021","journal-title":"J. Agric. Food Chem."},{"key":"ref_3","doi-asserted-by":"crossref","unstructured":"Chemat, F., Vian, M.A., Ravi, H.K., Khadhraoui, B., Hilali, S., Perino, S., and Tixier, A.S.F. (2019). 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