Publicação
Solubility of olive oil phenolic compounds in green solvents
| Resumo: | The production of olive oil generates various by-products that are rich in phenyl alcohols, secoiridoids, phenolic acids and aldehydes, flavonoids, and other bioactive compounds. Due to their diverse biological activities, these compounds have promising potential as functional additives in the food, pharmaceutical, and cosmetics industries.1 However, data on their solubility in water and common volatile organic solvents, as well as partitioning behavior—critical for optimizing extraction, purification, and formulation processes—remains very limited. In this study, the solubility of tyrosol (a phenyl alcohol) was experimentally determined in ten pure solvents and five aqueous binary solvent mixtures, using acetone, ethanol, 2-propanol, 1,3-butanediol, and 1,3-propanediol as co-solvents. Measurements were performed at 298 K using the analytical isothermal shake flask method. Additionally, the COnductor-like Screening MOdel for Real Solvents (COSMO-RS)3 using the default conformer distribution was employed to predict the solubility of tyrosol, hydroxytyrosol, and oleuropein in a wide range of pure organic solvents varying in polarity and functional groups, as well as in aqueous binary solvent mixtures. For tyrosol, the influence of solvent conformers and their apolar, hydrogen bond donor, and acceptor characteristics on COSMO-RS predictions was analyzed, as illustrated in Figure 1 for water–ethanol mixtures. Overall, the model effectively captures general solubility trends, though with reduced quantitative accuracy in polar aprotic solvents, indicating its utility for preliminary solvent selection. |
|---|---|
| Autores principais: | Vale, Mariana Ribeiro de Paula |
| Outros Autores: | Zambom, Aline; Krüger, Felipe; Martins, Mónia A. R.; Coutinho, João A.P.; Pinho, Simão; Peres, António M.; Ferreira, Olga |
| Assunto: | Olive oil Olives |
| Ano: | 2025 |
| País: | Portugal |
| Tipo de documento: | documento de conferência |
| Tipo de acesso: | acesso aberto |
| Instituição associada: | Instituto Politécnico de Bragança |
| Idioma: | inglês |
| Origem: | Biblioteca Digital do IPB |
| _version_ | 1867173099074486272 |
|---|---|
| author | Vale, Mariana Ribeiro de Paula |
| author2 | Zambom, Aline Krüger, Felipe Martins, Mónia A. R. Coutinho, João A.P. Pinho, Simão Peres, António M. Ferreira, Olga |
| author2_role | author author author author author author author |
| author_facet | Vale, Mariana Ribeiro de Paula Zambom, Aline Krüger, Felipe Martins, Mónia A. R. Coutinho, João A.P. Pinho, Simão Peres, António M. Ferreira, Olga |
| author_role | author |
| contributor_name_str_mv | Biblioteca Digital do IPB |
| country_str | PT |
| creators_json_txt | [{\"Person.name\":\"Vale, Mariana Ribeiro de Paula\"},{\"Person.name\":\"Zambom, Aline\"},{\"Person.name\":\"Krüger, Felipe\"},{\"Person.name\":\"Martins, Mónia A. R.\",\"Person.identifier.orcid\":\"0000-0003-0748-1612\"},{\"Person.name\":\"Coutinho, João A.P.\"},{\"Person.name\":\"Pinho, Simão\",\"Person.identifier.orcid\":\"0000-0002-9211-857X\"},{\"Person.name\":\"Peres, António M.\",\"Person.identifier.orcid\":\"0000-0001-6595-9165\"},{\"Person.name\":\"Ferreira, Olga\",\"Person.identifier.orcid\":\"0000-0001-8414-3479\"}] |
| datacite.contributors.contributor.contributorName.fl_str_mv | Biblioteca Digital do IPB |
| datacite.creators.creator.creatorName.fl_str_mv | Vale, Mariana Ribeiro de Paula Zambom, Aline Krüger, Felipe Martins, Mónia A. R. Coutinho, João A.P. Pinho, Simão Peres, António M. Ferreira, Olga |
| datacite.date.Accepted.fl_str_mv | 2025-01-01T00:00:00Z |
| datacite.date.available.fl_str_mv | 2025-11-05T11:04:08Z |
| datacite.date.embargoed.fl_str_mv | 2025-11-05T11:04:08Z |
| datacite.rights.fl_str_mv | http://purl.org/coar/access_right/c_abf2 |
| datacite.subjects.subject.fl_str_mv | Olive oil Olives |
| datacite.titles.title.fl_str_mv | Solubility of olive oil phenolic compounds in green solvents |
| dc.contributor.none.fl_str_mv | Biblioteca Digital do IPB |
| dc.creator.none.fl_str_mv | Vale, Mariana Ribeiro de Paula Zambom, Aline Krüger, Felipe Martins, Mónia A. R. Coutinho, João A.P. Pinho, Simão Peres, António M. Ferreira, Olga |
| dc.date.Accepted.fl_str_mv | 2025-01-01T00:00:00Z |
| dc.date.available.fl_str_mv | 2025-11-05T11:04:08Z |
| dc.date.embargoed.fl_str_mv | 2025-11-05T11:04:08Z |
| dc.format.none.fl_str_mv | application/pdf |
| dc.identifier.none.fl_str_mv | http://hdl.handle.net/10198/34951 |
| dc.language.none.fl_str_mv | eng |
| dc.publisher.none.fl_str_mv | University of Porto |
| dc.rights.cclincense.fl_str_mv | http://creativecommons.org/licenses/by/4.0/ |
| dc.rights.none.fl_str_mv | http://purl.org/coar/access_right/c_abf2 |
| dc.subject.none.fl_str_mv | Olive oil Olives |
| dc.title.fl_str_mv | Solubility of olive oil phenolic compounds in green solvents |
| dc.type.none.fl_str_mv | http://purl.org/coar/resource_type/c_c94f |
| description | The production of olive oil generates various by-products that are rich in phenyl alcohols, secoiridoids, phenolic acids and aldehydes, flavonoids, and other bioactive compounds. Due to their diverse biological activities, these compounds have promising potential as functional additives in the food, pharmaceutical, and cosmetics industries.1 However, data on their solubility in water and common volatile organic solvents, as well as partitioning behavior—critical for optimizing extraction, purification, and formulation processes—remains very limited. In this study, the solubility of tyrosol (a phenyl alcohol) was experimentally determined in ten pure solvents and five aqueous binary solvent mixtures, using acetone, ethanol, 2-propanol, 1,3-butanediol, and 1,3-propanediol as co-solvents. Measurements were performed at 298 K using the analytical isothermal shake flask method. Additionally, the COnductor-like Screening MOdel for Real Solvents (COSMO-RS)3 using the default conformer distribution was employed to predict the solubility of tyrosol, hydroxytyrosol, and oleuropein in a wide range of pure organic solvents varying in polarity and functional groups, as well as in aqueous binary solvent mixtures. For tyrosol, the influence of solvent conformers and their apolar, hydrogen bond donor, and acceptor characteristics on COSMO-RS predictions was analyzed, as illustrated in Figure 1 for water–ethanol mixtures. Overall, the model effectively captures general solubility trends, though with reduced quantitative accuracy in polar aprotic solvents, indicating its utility for preliminary solvent selection. |
| dirty | 0 |
| eu_rights_str_mv | openAccess |
| format | conferenceObject |
| fulltext.url.fl_str_mv | https://bibliotecadigital.ipb.pt/bitstreams/8145d5ea-b198-4d6e-bd5c-8b28365959eb/download |
| funding.funder.alternateName_str_mv | FCT FCT FCT FCT |
| funding.funder.identifier_str_mv | http://doi.org/10.13039/501100001871 http://doi.org/10.13039/501100001871 http://doi.org/10.13039/501100001871 http://doi.org/10.13039/501100001871 |
| funding.funder.name_str_mv | Fundação para a Ciência e a Tecnologia Fundação para a Ciência e a Tecnologia Fundação para a Ciência e a Tecnologia Fundação para a Ciência e a Tecnologia |
| funding.name_str_mv | 6817 - DCRRNI ID 6817 - DCRRNI ID 6817 - DCRRNI ID 6817 - DCRRNI ID |
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| identifier.url.fl_str_mv | http://hdl.handle.net/10198/34951 |
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| institution | Instituto Politécnico de Bragança |
| instname_str | Instituto Politécnico de Bragança |
| language | eng |
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| network_name_str | Biblioteca Digital do IPB |
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| organization_str_mv | urn:organizationAcronym:ipb |
| person_str_mv | Vale, Mariana Ribeiro de Paula Zambom, Aline Krüger, Felipe Martins, Mónia A. R. Martins, Mónia A. R. https://www.ciencia-id.pt/8117-0EEA-6B8E 8117-0EEA-6B8E http://orcid.org/0000-0003-0748-1612 0000-0003-0748-1612 Coutinho, João A.P. Pinho, Simão Pinho, Simão https://www.ciencia-id.pt/481D-73AD-8D0F 481D-73AD-8D0F http://orcid.org/0000-0002-9211-857X 0000-0002-9211-857X Peres, António M. Peres, António M. https://www.ciencia-id.pt/CF16-5443-F420 CF16-5443-F420 http://orcid.org/0000-0001-6595-9165 0000-0001-6595-9165 Ferreira, Olga Ferreira, Olga https://www.ciencia-id.pt/9F1D-C75A-4A54 9F1D-C75A-4A54 http://orcid.org/0000-0001-8414-3479 0000-0001-8414-3479 |
| publishDate | 2025 |
| publisher.none.fl_str_mv | University of Porto |
| reponame_str | Biblioteca Digital do IPB |
| repository_id_str | urn:repositoryAcronym:ipb |
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| spelling | engUniversity of PortoengThe production of olive oil generates various by-products that are rich in phenyl alcohols, secoiridoids, phenolic acids and aldehydes, flavonoids, and other bioactive compounds. Due to their diverse biological activities, these compounds have promising potential as functional additives in the food, pharmaceutical, and cosmetics industries.1 However, data on their solubility in water and common volatile organic solvents, as well as partitioning behavior—critical for optimizing extraction, purification, and formulation processes—remains very limited. In this study, the solubility of tyrosol (a phenyl alcohol) was experimentally determined in ten pure solvents and five aqueous binary solvent mixtures, using acetone, ethanol, 2-propanol, 1,3-butanediol, and 1,3-propanediol as co-solvents. Measurements were performed at 298 K using the analytical isothermal shake flask method. Additionally, the COnductor-like Screening MOdel for Real Solvents (COSMO-RS)3 using the default conformer distribution was employed to predict the solubility of tyrosol, hydroxytyrosol, and oleuropein in a wide range of pure organic solvents varying in polarity and functional groups, as well as in aqueous binary solvent mixtures. For tyrosol, the influence of solvent conformers and their apolar, hydrogen bond donor, and acceptor characteristics on COSMO-RS predictions was analyzed, as illustrated in Figure 1 for water–ethanol mixtures. Overall, the model effectively captures general solubility trends, though with reduced quantitative accuracy in polar aprotic solvents, indicating its utility for preliminary solvent selection.application/pdfporSolubility of olive oil phenolic compounds in green solventsVale, Mariana Ribeiro de PaulaZambom, AlineKrüger, FelipePersonalMartins, Mónia A. R.DSpacehttp://dspace.org/items/18f906f2-efcf-456c-b638-c921bbebe284DSpacehttp://dspace.org/items/18f906f2-efcf-456c-b638-c921bbebe284MartinsMónia A. R.Ciência IDhttps://www.ciencia-id.pt8117-0EEA-6B8EORCIDhttp://orcid.org0000-0003-0748-1612Scopus Author IDhttps://www.scopus.com56191802400Coutinho, João A.P.PersonalPinho, SimãoDSpacehttp://dspace.org/items/8ef7789a-34f3-4915-a666-4efe26272a30DSpacehttp://dspace.org/items/8ef7789a-34f3-4915-a666-4efe26272a30PinhoSimãoCiência IDhttps://www.ciencia-id.pt481D-73AD-8D0FORCIDhttp://orcid.org0000-0002-9211-857XResearcher IDhttps://www.researcherid.comD-4148-2013Scopus Author IDhttps://www.scopus.com7003570175PersonalPeres, António M.DSpacehttp://dspace.org/items/7d93be47-8dc4-4413-9304-5b978773d3bbDSpacehttp://dspace.org/items/7d93be47-8dc4-4413-9304-5b978773d3bbPeresAntónio M.Ciência IDhttps://www.ciencia-id.ptCF16-5443-F420ORCIDhttp://orcid.org0000-0001-6595-9165Researcher IDhttps://www.researcherid.comI-8470-2012Scopus Author IDhttps://www.scopus.com7102331969PersonalFerreira, OlgaDSpacehttp://dspace.org/items/59e0c608-0c21-4191-af5e-529d21970399DSpacehttp://dspace.org/items/59e0c608-0c21-4191-af5e-529d21970399FerreiraOlgaCiência IDhttps://www.ciencia-id.pt9F1D-C75A-4A54ORCIDhttp://orcid.org0000-0001-8414-3479Researcher IDhttps://www.researcherid.comM-4567-2013Scopus Author IDhttps://www.scopus.com57203083219HostingInstitutionOrganizationalBiblioteca Digital do IPBe-mailmailto:dspace@ipb.ptdspace@ipb.ptISBNIsPartOf978-989-35992-9-72025-11-05T11:04:08Z20252025-01-01T00:00:00ZHandlehttp://hdl.handle.net/10198/34951http://purl.org/coar/access_right/c_abf2open accessOlive oilOlives823411 bytesFundação para a Ciência e a TecnologiaMountain Research Center6817 - DCRRNI IDCrossref Funder IDhttp://doi.org/10.13039/501100001871Fundação para a Ciência e a TecnologiaCICECO-Aveiro Institute of Materials6817 - DCRRNI IDCrossref Funder IDhttp://doi.org/10.13039/501100001871Fundação para a Ciência e a TecnologiaMountain Research Center6817 - DCRRNI IDCrossref Funder IDhttp://doi.org/10.13039/501100001871Fundação para a Ciência e a TecnologiaCICECO – Aveiro Institute of Materials6817 - DCRRNI IDCrossref Funder IDhttp://doi.org/10.13039/501100001871other research producthttp://purl.org/coar/resource_type/c_c94fconference object2025http://creativecommons.org/licenses/by/4.0/http://purl.org/coar/access_right/c_abf2application/pdffulltexthttps://bibliotecadigital.ipb.pt/bitstreams/8145d5ea-b198-4d6e-bd5c-8b28365959eb/downloadBook of Abstracts of the 27th IUPAC International Conference on Chemical Thermodynamics ICCT2025169169Porto2025 |
| spellingShingle | Solubility of olive oil phenolic compounds in green solvents Vale, Mariana Ribeiro de Paula Olive oil Olives |
| status | SINGLETON |
| subject.fl_str_mv | Olive oil Olives |
| title | Solubility of olive oil phenolic compounds in green solvents |
| title_full | Solubility of olive oil phenolic compounds in green solvents |
| title_fullStr | Solubility of olive oil phenolic compounds in green solvents |
| title_full_unstemmed | Solubility of olive oil phenolic compounds in green solvents |
| title_short | Solubility of olive oil phenolic compounds in green solvents |
| title_sort | Solubility of olive oil phenolic compounds in green solvents |
| topic | Olive oil Olives |
| topic_facet | Olive oil Olives |
| url | http://hdl.handle.net/10198/34951 |
| visible | 1 |