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Octanol–water partition coefficients and aqueous solubility data of monoterpenoids: experimental, modeling, and environmental distribution

2022Journal article Open access
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dc.contributor.authorVilas-Boas, Sérgio M.
dc.contributor.authorCosta, Mariana C.
dc.contributor.authorCoutinho, João A.P.
dc.contributor.authorFerreira, Olga
dc.contributor.authorPinho, Simão
dc.date.accessioned2022-03-09T16:54:11Z
dc.date.available2022-03-09T16:54:11Z
dc.date.issued2022
dc.description.abstractTerpenes and terpenoids encompass one of the most extensive and valuable classes of secondary metabolites. Their ten-carbon-containing oxygenated representatives, monoterpenoids, are the main components of plant essential oils, being widely exploited in the cosmetic, pharmaceutical, and food industrial areas. Due to its widespread use, it is crucial to investigate their environmental distribution. Thus, new water solubility data were obtained for six monoterpenoids ((1R)-(+)-camphor, (S)-(+)-carvone, eucalyptol, (1R)- (−)-fenchone, L-(−)-menthol, and (−)-menthone) at 298.2 and 313.2 K. Furthermore, octanol−water partition coefficients of 12 monoterpenoids (the six mentioned above plus carvacrol, (±)-β-citronellol, eugenol, geraniol, linalool, and thymol) were measured at 298.2 K. The COSMO-RS thermodynamic model and other more empirical approaches were evaluated for the description of the solubilities and partition coefficients, showing reliable predictions. Lastly, the distribution of the monoterpenoids in the different environmental compartments was assessed through an intuitive two-dimensional chemical space diagram based on the physicochemical equilibrium information reported.pt_PT
dc.description.sponsorshipThis work was developed within the scope of the project CIMO-Mountain Research Center, UIDB/00690/2020, and CICECO-Aveiro Institute of Materials, UIDB/50011/2020 and UIDP/50011/2020, financed by national funds through the Portuguese Foundation for Science and Technology (FCT)/MCTES. S.M.V.-B. thanks FCT and the European Social Fund (ESF) for his Ph.D. grant (SFRH/BD/138149/2018). M.C.d.C. would also like to thank CNPq (306666/ 2020-0) and FAPESP (2014/21252-0).pt_PT
dc.description.versioninfo:eu-repo/semantics/publishedVersionpt_PT
dc.identifier.citationVilas-Boas, Sérgio M.; Costa, Mariana C. Da; Coutinho, João A. P.; Ferreira, Olga; Pinho, Simão (2022). Octanol–water partition coefficients and aqueous solubility data of monoterpenoids: experimental, modeling, and environmental distribution. Industrial & Engineering Chemistry Research. ISSN 0888-5885. 61:8, p. 3154-3167pt_PT
dc.identifier.doi10.1021/acs.iecr.1c04196pt_PT
dc.identifier.issnISSN 0888-5885
dc.identifier.urihttp://hdl.handle.net/10198/25190
dc.language.isoengpt_PT
dc.peerreviewedyespt_PT
dc.publisherACSpt_PT
dc.relationMountain Research Center
dc.relationCICECO-Aveiro Institute of Materials
dc.relationCICECO-Aveiro Institute of Materials
dc.relationNovos Processos de Separação para o Fracionamento e Purificação de Terpenos
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/pt_PT
dc.subjectEssential oilspt_PT
dc.subjectMetabolitespt_PT
dc.subjectSolubilitypt_PT
dc.titleOctanol–water partition coefficients and aqueous solubility data of monoterpenoids: experimental, modeling, and environmental distributionpt_PT
dc.typejournal article
dspace.entity.typePublication
oaire.awardTitleMountain Research Center
oaire.awardTitleCICECO-Aveiro Institute of Materials
oaire.awardTitleCICECO-Aveiro Institute of Materials
oaire.awardTitleNovos Processos de Separação para o Fracionamento e Purificação de Terpenos
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDB%2F00690%2F2020/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDB%2F50011%2F2020/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDP%2F50011%2F2020/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT//SFRH%2FBD%2F138149%2F2018/PT
oaire.citation.endPage3167pt_PT
oaire.citation.issue8pt_PT
oaire.citation.startPage3154pt_PT
oaire.citation.titleIndustrial & Engineering Chemistry Researchpt_PT
oaire.citation.volume61pt_PT
oaire.fundingStream6817 - DCRRNI ID
oaire.fundingStream6817 - DCRRNI ID
oaire.fundingStream6817 - DCRRNI ID
person.familyNameFerreira
person.familyNamePinho
person.givenNameOlga
person.givenNameSimão
person.identifier810882
person.identifier.ciencia-id9F1D-C75A-4A54
person.identifier.ciencia-id481D-73AD-8D0F
person.identifier.orcid0000-0001-8414-3479
person.identifier.orcid0000-0002-9211-857X
person.identifier.ridM-4567-2013
person.identifier.ridD-4148-2013
person.identifier.scopus-author-id57203083219
person.identifier.scopus-author-id7003570175
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
rcaap.rightsopenAccesspt_PT
rcaap.typearticlept_PT
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