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Partitioning is also of general interest in the oil industry. Edible oils such as olive oil contain a variety of bioactive components that, depending on their partition constants, end up in an aqueous phase when extracted from olive fruits. Frequently, waste waters are subsequently discarded, but their recovery would allow for obtaining extracts with antioxidant and\/or biological activities, adding commercial value to the wastes and, at the same time, would allow for minimizing environmental risks. Thus, given the importance of partitioning antioxidants, in this manuscript, we review the background theory necessary to derive the relevant equations necessary to describe, quantitatively, the partitioning of antioxidants (and, in general, other drugs) and the common methods for determining their partition constants in both binary (PWOIL) and multiphasic systems composed with edible oils. We also include some discussion on the usefulness (or not) of extrapolating the widely employed octanol\u2013water partition constant (PWOCT) values to predict PWOIL values as well as on the effects of acidity and temperature on their distributions. Finally, there is a brief section discussing the importance of partitioning in lipidic oil-in-water emulsions, where two partition constants, that between the oil-interfacial, POI, and that between aqueous-interfacial, PwI, regions, which are needed to describe the partitioning of antioxidants, and whose values cannot be predicted from the PWOIL or the PWOCT ones.<\/jats:p>","DOI":"10.3390\/antiox12040828","type":"journal-article","created":{"date-parts":[[2023,3,28]],"date-time":"2023-03-28T07:05:25Z","timestamp":1679987125000},"page":"828","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":12,"title":["Partitioning of Antioxidants in Edible Oil\u2013Water Binary Systems and in Oil-in-Water Emulsions"],"prefix":"10.3390","volume":"12","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-9447-5626","authenticated-orcid":false,"given":"Sonia","family":"Losada-Barreiro","sequence":"first","affiliation":[{"name":"Departamento Qu\u00edmica-F\u00edsica, Facultad de Qu\u00edmica, Universidade de Vigo, 36310 Vigo, Spain"},{"name":"REQUIMTE-LAQV, Departamento de Qu\u00edmica e Bioqu\u00edmica, Faculdade de Ci\u00eancias, Universidade do Porto, 4169-007 Porto, Portugal"}]},{"given":"F\u00e1tima","family":"Paiva-Martins","sequence":"additional","affiliation":[{"name":"REQUIMTE-LAQV, Departamento de Qu\u00edmica e Bioqu\u00edmica, Faculdade de Ci\u00eancias, Universidade do Porto, 4169-007 Porto, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9468-0881","authenticated-orcid":false,"given":"Carlos","family":"Bravo-D\u00edaz","sequence":"additional","affiliation":[{"name":"Departamento Qu\u00edmica-F\u00edsica, Facultad de Qu\u00edmica, Universidade de Vigo, 36310 Vigo, Spain"}]}],"member":"1968","published-online":{"date-parts":[[2023,3,28]]},"reference":[{"key":"ref_1","first-page":"69","article-title":"Recovery and Concentration of Antioxidants from Industrial Effluents and from Processing Streams of Underutilized Vegetal Biomass","volume":"3","author":"Conde","year":"2013","journal-title":"Food Public Health"},{"key":"ref_2","doi-asserted-by":"crossref","unstructured":"Ben-Othman, S., J\u00f5udu, I., and Bhat, R. (2020). Bioactives from Agri-Food Wastes: Present Insights and Future Challenges. Molecules, 25.","DOI":"10.3390\/molecules25030510"},{"key":"ref_3","doi-asserted-by":"crossref","unstructured":"Louren\u00e7o, S.C., Mold\u00e3o-Martins, M., and Alves, V.D. (2019). Antioxidants of Natural Plant Origins: From Sources to Food Industry Applications. Molecules, 24.","DOI":"10.3390\/molecules24224132"},{"key":"ref_4","doi-asserted-by":"crossref","unstructured":"Costa, M., Sezgin-Bayindir, Z., Losada-Barreiro, S., Paiva-Martins, F., Saso, L., and Bravo-D\u00edaz, C. (2021). Polyphenols as Antioxidants for Extending Food Shelf-Life and in the Prevention of Health Diseases: Encapsulation and Interfacial Phenomena. Biomedicines, 9.","DOI":"10.3390\/biomedicines9121909"},{"key":"ref_5","unstructured":"Milani, J.M. (2018). Some New Aspects of Colloidal Systems in Foods, IntechOpen."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"41","DOI":"10.1080\/10942912.2020.1866597","article-title":"Antioxidant-rich natural fruit and vegetable products and human health","volume":"24","author":"Jideani","year":"2021","journal-title":"Int. J. Food Prop."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"108849","DOI":"10.1016\/j.foodres.2019.108849","article-title":"Antioxidant compounds from microbial sources: A review","volume":"129","author":"Chandra","year":"2020","journal-title":"Food Res. Int."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"127","DOI":"10.1016\/j.jfoodeng.2009.07.007","article-title":"Recovery of antioxidants from industrial waste liquors using membranes and polymeric resins","volume":"96","author":"Moure","year":"2010","journal-title":"J. Food Eng."},{"key":"ref_9","doi-asserted-by":"crossref","unstructured":"Fierascu, R.C., Fierascu, I., Avramescu, S.M., and Sieniawska, E. (2019). Recovery of Natural Antioxidants from Agro-Industrial Side Streams through Advanced Extraction Techniques. Molecules, 24.","DOI":"10.3390\/molecules24234212"},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"116602","DOI":"10.1016\/j.watres.2020.116602","article-title":"Diphenylamine Antioxidants in wastewater influent, effluent, biosolids and landfill leachate: Contribution to environmental releases","volume":"189","author":"Zhang","year":"2021","journal-title":"Water Res."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"615","DOI":"10.1007\/s10646-011-0806-y","article-title":"Olive oil mill wastewaters before and after treatment: A critical review from the ecotoxicological point of view","volume":"21","author":"Justino","year":"2012","journal-title":"Ecotoxicology"},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"447","DOI":"10.1016\/j.procbio.2005.07.014","article-title":"Antioxidant properties of ultrafiltration-recovered soy protein fractions from industrial effluents and their hydrolysates","volume":"41","author":"Moure","year":"2006","journal-title":"Process Biochem."},{"key":"ref_13","doi-asserted-by":"crossref","unstructured":"Melini, V., Melini, F., Luziatelli, F., and Ruzzi, M. (2020). Functional Ingredients from Agri-Food Waste: Effect of Inclusion Thereof on Phenolic Compound Content and Bioaccessibility in Bakery Products. Antioxidants, 9.","DOI":"10.3390\/antiox9121216"},{"key":"ref_14","doi-asserted-by":"crossref","unstructured":"Stromsnes, K., Lagzdina, R., Olaso-Gonzalez, G., Gimeno-Mallench, L., and Gambini, J. (2021). Pharmacological Properties of Polyphenols: Bioavailability, Mechanisms of Action, and Biological Effects in In Vitro Studies, Animal Models, and Humans. Biomedicines, 9.","DOI":"10.3390\/biomedicines9081074"},{"key":"ref_15","doi-asserted-by":"crossref","unstructured":"Bravo-Diaz, C. (2022). Lipid Oxidation in Food and Biological Systems: A Physical Chemistry Perspective, Springer International Publishing.","DOI":"10.1007\/978-3-030-87222-9"},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"7151","DOI":"10.1021\/jf801154r","article-title":"Antioxidant activity of oregano, parsley, and olive mill wastewaters in bulk oils and oil-in-water emulsions enriched in fish oil","volume":"56","author":"Giuffrida","year":"2008","journal-title":"J. Agric. Food Chem."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"993","DOI":"10.1016\/j.ijbiomac.2019.05.175","article-title":"Preparation of pH-sensitive and antioxidant packaging films based on \u03ba-carrageenan and mulberry polyphenolic extract","volume":"134","author":"Liu","year":"2019","journal-title":"Int. J. Biol. Macromol."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"93","DOI":"10.1016\/j.foodres.2018.06.073","article-title":"Active packaging films with natural antioxidants to be used in meat industry: A review","volume":"113","author":"Barba","year":"2018","journal-title":"Food Res. Int."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"1237","DOI":"10.1080\/19440049.2021.1885745","article-title":"Plant-derived antioxidants incorporated into active packaging intended for vegetables and fatty animal products: A review","volume":"38","author":"Zhang","year":"2021","journal-title":"Food Addit. Contam. Part A Chem. Anal. Control Expo. Risk Assess."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"998","DOI":"10.1016\/j.foodchem.2005.10.057","article-title":"Studies on oxidative stabilisation of lard by natural antioxidants recovered from olive-oil mill wastewater","volume":"100","author":"Macciola","year":"2007","journal-title":"Food Chem."},{"key":"ref_21","unstructured":"Leo, A.J. (2002). Encyclopedia of Computational Chemistry, John Wiley & Sons, Ltd."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1016\/j.chroma.2004.01.001","article-title":"Determination of liquid-liquid partition coefficients by separation methods","volume":"1037","author":"Berthod","year":"2004","journal-title":"J. Chromatog. A"},{"key":"ref_23","unstructured":"Poole, C.F. (2020). Liquid-Phase Extraction, Elsevier."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"369","DOI":"10.1016\/j.ejps.2018.01.029","article-title":"Accessing lipophilicity of drugs with biomimetic models: A comparative study using liposomes and micelles","volume":"115","author":"Loureiro","year":"2018","journal-title":"Eur. J. Pharm. Sci."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"045102","DOI":"10.1063\/1.4890877","article-title":"Predicting solute partitioning in lipid bilayers: Free energies and partition coefficients from molecular dynamics simulations and COSMOmic","volume":"141","author":"Jakobtorweihen","year":"2014","journal-title":"J. Chem. Phys."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"11","DOI":"10.1016\/j.jct.2013.01.022","article-title":"Partition coefficients and thermodynamics of transfer of novel drug-like spiro-derivatives in model biological solutions","volume":"61","author":"Blokhina","year":"2013","journal-title":"J. Chem. Thermodyn."},{"key":"ref_27","unstructured":"Sangster, J. (1997). Octanol-Water Partition coefficients, Fundamentals and Physcial Chemistry, J. Wiley & Sons."},{"key":"ref_28","doi-asserted-by":"crossref","unstructured":"Dini, I. (2022). Contribution of Nanoscience Research in Antioxidants Delivery Used in Nutricosmetic Sector. Antioxidants, 11.","DOI":"10.3390\/antiox11030563"},{"key":"ref_29","doi-asserted-by":"crossref","unstructured":"Sezgin-Bayindir, Z., Losada-Barreiro, S., Bravo-D\u00edaz, C., Sova, M., Kristl, J., and Saso, L. (2021). Nanotechnology-Based Drug Delivery to Improve the Therapeutic Benefits of NRF2 Modulators in Cancer Therapy. Antioxidants, 10.","DOI":"10.3390\/antiox10050685"},{"key":"ref_30","doi-asserted-by":"crossref","unstructured":"Aboudzadeh, M.A. (2021). Emulsion-Based Encapsulation of Antioxidants, Springer Nature.","DOI":"10.1007\/978-3-030-62052-3"},{"key":"ref_31","doi-asserted-by":"crossref","unstructured":"Garc\u00eda-P\u00e9rez, P., Losada-Barreiro, S., Gallego, P.P., and Bravo-D\u00edaz, C. (2019). Cyclodextrin-Elicited Bryophyllum Suspension Cultured Cells: Enhancement of the Production of Bioactive Compounds. Int. J. Mol. Sci., 20.","DOI":"10.20944\/preprints201910.0097.v1"},{"key":"ref_32","unstructured":"Grumezescu, A.M. (2018). Drug Targeting and Stimuli Sensitive Drug Delivery Systems, William Andrew Publishing."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"1064","DOI":"10.1021\/mp800059u","article-title":"Modeling Free Energies of Solvation in Olive Oil","volume":"5","author":"Chamberlin","year":"2008","journal-title":"Mol. Pharm."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"327","DOI":"10.1016\/0022-5193(65)90081-0","article-title":"A hypothesis relating oil: Water partition coefficients and vapor pressures of nonelectrolytes to their penetration rates through biological membranes","volume":"8","author":"Coe","year":"1965","journal-title":"J. Theor. Biol."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"57","DOI":"10.1021\/es00131a005","article-title":"Partition coefficients of organic compounds in lipid-water systems and correlations with fish bioconcentration factors","volume":"19","author":"Chiou","year":"1985","journal-title":"Environ. Sci. Technol."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"962","DOI":"10.1007\/s11095-010-0303-7","article-title":"Lipophilicity and Its Relationship with Passive Drug Permeation","volume":"28","author":"Liu","year":"2011","journal-title":"Pharm. Res."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"436","DOI":"10.1002\/1520-6017(200104)90:4<436::AID-JPS1002>3.0.CO;2-P","article-title":"Prediction of adipose tissue: Plasma partition coefficients for structurally unrelated drugs","volume":"90","author":"Poulin","year":"2001","journal-title":"J. Pharm. Sci."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"17","DOI":"10.1111\/j.1749-6632.1988.tb22317.x","article-title":"Membrane antioxidants","volume":"551","author":"Krinsky","year":"1988","journal-title":"Ann. N.Y. Acad. Sci."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"2027","DOI":"10.1021\/cr00031a013","article-title":"Molecular Interactions in Solution: An Overview of Methods Based on Continuous Distributions of the Solvent","volume":"94","author":"Tomasi","year":"1994","journal-title":"Chem. Rev."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"266","DOI":"10.1021\/mp7000878","article-title":"Predicting Intrinsic Aqueous Solubility by a Thermodynamic Cycle","volume":"5","author":"Palmer","year":"2008","journal-title":"Mol. Pharm."},{"key":"ref_41","doi-asserted-by":"crossref","unstructured":"Bravo-Diaz, C. (2022). Lipid Oxidation in Food and Biological Systems: A Physical Chemistry Perspective, Springer International Publishing.","DOI":"10.1007\/978-3-030-87222-9"},{"key":"ref_42","doi-asserted-by":"crossref","unstructured":"Bravo-Diaz, C. (2022). Lipid Oxidation in Food and Biological Systems: A Physical Chemistry Perspective, Springer International Publishing.","DOI":"10.1007\/978-3-030-87222-9"},{"key":"ref_43","doi-asserted-by":"crossref","unstructured":"Bravo-Diaz, C. (2022). Lipid Oxidation in Food and Biological Systems: A Physical Chemistry Perspective, Springer International Publishing.","DOI":"10.1007\/978-3-030-87222-9"},{"key":"ref_44","doi-asserted-by":"crossref","unstructured":"Bravo-Diaz, C. (2022). Lipid Oxidation in Food and Biological Systems: A Physical Chemistry Perspective, Springer International Publishing.","DOI":"10.1007\/978-3-030-87222-9"},{"key":"ref_45","first-page":"1","article-title":"Advances in the control of lipid peroxidation in oil-in-water emulsions: Kinetic approaches","volume":"1","year":"2022","journal-title":"Crit. Rev. Food Sci. Nutr."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"1275","DOI":"10.1111\/1541-4337.12890","article-title":"Lipid oxidation and antioxidant delivery systems in muscle food","volume":"21","author":"Wu","year":"2022","journal-title":"Compr. Rev. Food Sci. Food Saf."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"9897464","DOI":"10.34133\/2022\/9897464","article-title":"Advances in Delivering Oxidative Modulators for Disease Therapy","volume":"2022","author":"Yang","year":"2022","journal-title":"Research"},{"key":"ref_48","unstructured":"Nic, M., Jirat, J., Kosata, J., Jenkins, A., and McNaught, A. (2019). Compendium of Chemical Terminology. Gold Book, IUPAC, (Web 2.0 Version), IUPAC."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"525","DOI":"10.1021\/cr60274a001","article-title":"Partition Coefficients And Their Uses","volume":"71","author":"Leo","year":"1971","journal-title":"Chem. Rev."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"9284","DOI":"10.1021\/acs.iecr.6b02040","article-title":"Prediction of pH Effect on the Octanol\u2013Water Partition Coefficient of Ionizable Pharmaceuticals","volume":"55","author":"Chen","year":"2016","journal-title":"Ind. Eng. Chem. Res."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"4015","DOI":"10.1021\/acs.jctc.6b00449","article-title":"Calculating Partition Coefficients of Small Molecules in Octanol\/Water and Cyclohexane\/Water","volume":"12","author":"Bannan","year":"2016","journal-title":"J. Chem. Theory Comput."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"67","DOI":"10.2174\/156802610790232233","article-title":"Hydrophobicity--shake flasks, protein folding and drug discovery","volume":"10","author":"Sarkar","year":"2010","journal-title":"Curr. Top. Med. Chem."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"105","DOI":"10.1017\/S0033583501003687","article-title":"Intermolecular forces in biology","volume":"34","author":"Leckband","year":"2001","journal-title":"Q. Rev. Biophys."},{"key":"ref_54","unstructured":"Atkins, P., and de Paula, J. (2022). Physical Chemistry, Oxford University Press."},{"key":"ref_55","unstructured":"Israelachvili, J. (2011). Intermolecular and Surface Forces, Elsevier. [3rd ed.]."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"1539","DOI":"10.1021\/jo00810a023","article-title":"Linear free energy relations between partitioning solvent systems","volume":"36","author":"Leo","year":"1971","journal-title":"J. Org. Chem."},{"key":"ref_57","doi-asserted-by":"crossref","unstructured":"Schwarzenbach, R.P., Gschwend, P.M., and Imboden, D.M. (2002). Environmental Organic Chemistry, J. Wiley & Sons.","DOI":"10.1002\/0471649643"},{"key":"ref_58","unstructured":"Hansch, C., Leo, A., and Hoelkman, D. (1995). Exploring QSAR: Fundamentals and Applications in Chemistry and Biology, American Chemical Society."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"9868","DOI":"10.1021\/acs.jpcb.7b08311","article-title":"Prediction of pH-Dependent Hydrophobic Profiles of Small Molecules from Miertus\u2013Scrocco\u2013Tomasi Continuum Solvation Calculations","volume":"121","author":"Zamora","year":"2017","journal-title":"J. Phys. Chem. B"},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"54","DOI":"10.1016\/j.trac.2019.01.011","article-title":"State of the art and prospects of methods for determination of lipophilicity of chemical compounds","volume":"113","author":"Chmiel","year":"2019","journal-title":"TrAC Trends Anal. Chem."},{"key":"ref_61","first-page":"2","article-title":"Experimental Measurements of Octanol-Water Partition Coefficients of Ionic Liquids","volume":"5","author":"Trigo","year":"2015","journal-title":"J. Adv. Chem. Eng."},{"key":"ref_62","doi-asserted-by":"crossref","unstructured":"Berthod, A., and Garc\u00eda \u00c1lvarez-Coque, M.C. (2000). Micellar Liquid Chromatography, Marcel Dekker.","DOI":"10.1201\/9781482273816"},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"28","DOI":"10.1016\/j.trac.2015.02.009","article-title":"Recent advances in lipophilicity measurement by reversed-phase high-performance liquid chromatography","volume":"68","author":"Liang","year":"2015","journal-title":"TrAC Trends Anal. Chem."},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"31","DOI":"10.1016\/j.chroma.2015.09.003","article-title":"Simultaneous determination of hydrophobicity and dissociation constant for a large set of compounds by gradient reverse phase high performance liquid chromatography\u2013mass spectrometry technique","volume":"1416","author":"Kubik","year":"2015","journal-title":"J. Chromatogr. A"},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"3212","DOI":"10.1021\/cr068412z","article-title":"QSRR:\u2009 Quantitative Structure-(Chromatographic) Retention Relationships","volume":"107","author":"Kaliszan","year":"2007","journal-title":"Chem. Rev."},{"key":"ref_66","unstructured":"Tetko, I.V., Yan, A., and Gasteiger, J. (2018). Applied Chemoinformatics, Wiley."},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"2999","DOI":"10.1021\/acs.jced.8b00258","article-title":"Differential Partitioning of Bioantioxidants in Edible Oil\u2013Water and Octanol\u2013Water Systems: Linear Free Energy Relationships","volume":"63","year":"2018","journal-title":"J. Chem. Eng. Data"},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"539","DOI":"10.3390\/foods10030539","article-title":"Polyphenolic Antioxidants in Lipid Emulsions: Partitioning Effects and Interfacial Phenomena","volume":"10","author":"Costa","year":"2021","journal-title":"Foods"},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"120","DOI":"10.1016\/j.fluid.2014.01.014","article-title":"Octanol\/water partition coefficients Kow: A critical examination of the value of the methylene group contribution to logKow for homologous series of organic compounds","volume":"368","author":"Molyneux","year":"2014","journal-title":"Fluid Phase Equilibria"},{"key":"ref_70","doi-asserted-by":"crossref","first-page":"26","DOI":"10.1016\/j.envres.2015.09.025","article-title":"Evaluation of QSAR models for predicting the partition coefficient (logP) of chemicals under the REACH regulation","volume":"143","author":"Cappelli","year":"2015","journal-title":"Environ. Res."},{"key":"ref_71","doi-asserted-by":"crossref","first-page":"101","DOI":"10.1146\/annurev-chembioeng-073009-100903","article-title":"COSMO-RS: An alternative to simulation for calculating thermodynamic properties of liquid mixtures","volume":"1","author":"Klamt","year":"2010","journal-title":"Annu. Rev. Chem. Biomol. Eng."},{"key":"ref_72","doi-asserted-by":"crossref","first-page":"1410","DOI":"10.1002\/jps.2600841206","article-title":"Comparative Evaluation of the Predictive Power of Calculation Procedures for Molecular Lipophilicity","volume":"84","author":"Mannhold","year":"1995","journal-title":"J. Pharm. Sci."},{"key":"ref_73","doi-asserted-by":"crossref","first-page":"774","DOI":"10.1111\/j.2042-7158.1987.tb05118.x","article-title":"A thermodynamic analysis of the Collander equation and establishment of a reference solvent for use in drug partitioning studies","volume":"39","author":"Beezer","year":"1987","journal-title":"J. Pharm. Pharmacol."},{"key":"ref_74","unstructured":"(2023, February 23). Molinspiration. Available online: https:\/\/www.molinspiration.com\/."},{"key":"ref_75","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1021\/es000996d","article-title":"Linear Free Energy Relationships Used To Evaluate Equilibrium Partitioning of Organic Compounds","volume":"35","author":"Goss","year":"2001","journal-title":"Environ. Sci. Technol."},{"key":"ref_76","first-page":"4250","article-title":"A comprehensive review on polarity, partitioning, and interactions of phenolic antioxidants at oil\u2013water interface of food emulsions","volume":"20","author":"Farooq","year":"2021","journal-title":"Nat. Antioxid. Sources Compd."},{"key":"ref_77","doi-asserted-by":"crossref","first-page":"1385173","DOI":"10.1080\/23312009.2017.1385173","article-title":"Determination of distribution constants of antioxidants by electrokinetic chromatography","volume":"3","author":"Liimatta","year":"2017","journal-title":"Cogent Chem."},{"key":"ref_78","doi-asserted-by":"crossref","first-page":"1801","DOI":"10.1002\/ejlt.201400507","article-title":"Distributions of phenolic acid antioxidants between the interfacial and aqueous regions of corn oil emulsions: Effects of pH and emulsifier concentration","volume":"117","author":"Romsted","year":"2015","journal-title":"Eur. J. Lipid Sci. Technol."},{"key":"ref_79","unstructured":"Dean, J.A. (1992). Lange\u00b4s Handbook of Chemistry, McGraw-Hill, Inc."},{"key":"ref_80","doi-asserted-by":"crossref","first-page":"1305","DOI":"10.1007\/s10953-008-9305-z","article-title":"Nonaqueous Solution Studies on the Protonation Equilibria of some Phenolic Acids","volume":"37","author":"Fazary","year":"2008","journal-title":"J. Solut. Chem."},{"key":"ref_81","doi-asserted-by":"crossref","first-page":"807","DOI":"10.1021\/je800595x","article-title":"Determination of Dissociation Constants of Some Hydroxylated Benzoic and Cinnamic Acids in Water from Mobility and Spectroscopic Data Obtained by CE-DAD","volume":"54","author":"Ozkorucuklu","year":"2009","journal-title":"J. Chem. Eng. Data"},{"key":"ref_82","doi-asserted-by":"crossref","first-page":"8291","DOI":"10.1021\/bi201195u","article-title":"Trolox, a Water-Soluble Analogue of \u03b1-Tocopherol, Photoprotects the Surface-Exposed Regions of the Photosystem II Reaction Center in Vitro. Is This Physiologically Relevant?","volume":"50","author":"Arellano","year":"2011","journal-title":"Biochem."},{"key":"ref_83","doi-asserted-by":"crossref","first-page":"224","DOI":"10.1016\/j.jcis.2019.07.085","article-title":"Enhancing the fraction of antioxidants at the interfaces of oil-in-water emulsions: A kinetic and thermodynamic analysis of their partitioning","volume":"555","year":"2019","journal-title":"J. Colloid Interface Sci."},{"key":"ref_84","doi-asserted-by":"crossref","first-page":"2646","DOI":"10.1021\/la803224j","article-title":"Effects of Temperature and Emulsifier Concentration on \u03b1-Tocopherol Distribution in a Stirred, Fluid, Emulsion. Thermodynamics of \u03b1-Tocopherol transfer between the Oil and Interfacial Regions","volume":"25","author":"Gunaseelan","year":"2009","journal-title":"Langmuir"},{"key":"ref_85","doi-asserted-by":"crossref","unstructured":"McClements, D.J. (2015). Food Emulsions, Principles, Practices and Techniques, CRC Press.","DOI":"10.1201\/b18868"},{"key":"ref_86","doi-asserted-by":"crossref","first-page":"415","DOI":"10.1016\/j.foodhyd.2005.10.009","article-title":"Food emulsions\u2014Their structures and structure-forming properties","volume":"20","author":"Dalgleish","year":"2006","journal-title":"Food Hydrocoll."},{"key":"ref_87","doi-asserted-by":"crossref","first-page":"84","DOI":"10.1016\/j.cocis.2017.09.001","article-title":"Chemical kinetic and chemical trapping methods: Unique approaches for determining respectively the antioxidant distributions and interfacial molarities of water, counter-anions, and other weakly basic nucleophiles in association colloids","volume":"32","author":"Dar","year":"2017","journal-title":"Curr. Opin. Colloid Interface Sci."},{"key":"ref_88","doi-asserted-by":"crossref","first-page":"8961","DOI":"10.1021\/acs.langmuir.5b00112","article-title":"To Model Chemical Reactivity in Heterogeneous Emulsions, Think Homogeneous Microemulsions","volume":"31","author":"Romsted","year":"2015","journal-title":"Langmuir"},{"key":"ref_89","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1016\/j.cocis.2012.11.001","article-title":"Modelling chemical reactivity in emulsions","volume":"18","author":"Romsted","year":"2013","journal-title":"Curr. Opin. Colloid Interface Sci."},{"key":"ref_90","first-page":"4004","article-title":"Transfer of antioxidants at the interfaces of model food emulsions: Distributions and thermodynamic parameters","volume":"6","year":"2008","journal-title":"Org. Biomol. Chem."},{"key":"ref_91","doi-asserted-by":"crossref","first-page":"5274","DOI":"10.1021\/acs.jafc.6b01468","article-title":"Interfacial Concentrations of Hydroxytyrosol and Its Lipophilic Esters in Intact Olive Oil-in-Water Emulsions: Effects of Antioxidant Hydrophobicity, Surfactant Concentration, and the Oil-to-Water Ratio on the Oxidative Stability of the Emulsions","volume":"64","author":"Almeida","year":"2016","journal-title":"J. Agric. Food Chem."},{"key":"ref_92","doi-asserted-by":"crossref","first-page":"233","DOI":"10.1016\/j.foodchem.2014.10.016","article-title":"A direct correlation between the antioxidant efficiencies of caffeic acid and its alkyl esters and their concentrations in the interfacial region of olive oil emulsions. The pseudophase model interpretation of the \u2018\u2018cut-off\u2019\u2019 effect","volume":"175","author":"Costa","year":"2015","journal-title":"Food Chem."},{"key":"ref_93","doi-asserted-by":"crossref","unstructured":"Costa, M., Losada-Barreiro, S., Bravo-D\u00edaz, C., Monteiro, L.S., and Paiva-Martins, F. (2020). Interfacial Concentrations of Hydroxytyrosol Derivatives in Fish Oil-in-Water Emulsions and Nanoemulsions and Its Influence on Their Lipid Oxidation: Droplet Size Effects. Foods, 9.","DOI":"10.3390\/foods9121897"},{"key":"ref_94","doi-asserted-by":"crossref","first-page":"352","DOI":"10.1016\/j.jcis.2019.12.011","article-title":"Effects of droplet size on the interfacial concentrations of antioxidants in fish and olive oil-in-water emulsions and nanoemulsions and on their oxidative stability","volume":"562","author":"Costa","year":"2020","journal-title":"J. Colloid Interface Sci."},{"key":"ref_95","doi-asserted-by":"crossref","first-page":"125716","DOI":"10.1016\/j.foodchem.2019.125716","article-title":"Influence of AO chain length, droplet size and oil to water ratio on the distribution and on the activity of gallates in fish oil-in-water emulsified systems: Emulsion and nanoemulsion comparison","volume":"310","author":"Costa","year":"2020","journal-title":"Food Chem."},{"key":"ref_96","doi-asserted-by":"crossref","first-page":"4429","DOI":"10.1039\/C8FO00977E","article-title":"Enhancement of the antioxidant efficiency of gallic acid derivatives in intact fish oil-in-water emulsions through optimization of their interfacial concentrations","volume":"9","year":"2018","journal-title":"Food Funct."},{"key":"ref_97","doi-asserted-by":"crossref","first-page":"380","DOI":"10.1007\/s11483-014-9332-9","article-title":"Influence of Temperature on the Distribution of Catechin in Corn oil-in-water Emulsions and some Relevant Thermodynamic Parameters","volume":"9","author":"Romsted","year":"2014","journal-title":"Food Biophys."},{"key":"ref_98","doi-asserted-by":"crossref","unstructured":"Losada-Barreiro, S., Bravo-D\u00edaz, C., Costa, M., and Paiva-Martins, F. (2013). Distribution of catechol in emulsions. J. Phys. Org. Chem., in press.","DOI":"10.1002\/poc.3196"},{"key":"ref_99","doi-asserted-by":"crossref","first-page":"91483","DOI":"10.1039\/C6RA18282H","article-title":"Optimizing the efficiency of antioxidants in emulsions by lipophilization: Tuning interfacial concentrations","volume":"6","author":"Costa","year":"2016","journal-title":"RSC Adv."},{"key":"ref_100","doi-asserted-by":"crossref","first-page":"6533","DOI":"10.1021\/jf400981x","article-title":"Maxima in antioxidant distributions and efficiencies with increasing hydrophobicity of gallic acid and its alkyl esters. The pseudophase model interpretation of the \u201cCut-off effect","volume":"61","author":"Romsted","year":"2013","journal-title":"J. Agric. Food Chem."},{"key":"ref_101","doi-asserted-by":"crossref","first-page":"903","DOI":"10.1007\/s10450-019-00108-3","article-title":"Concentration of resveratrol at the oil\u2013water interface of corn oil-in-water emulsions","volume":"25","author":"Szymula","year":"2019","journal-title":"Adsorption"},{"key":"ref_102","doi-asserted-by":"crossref","first-page":"7318","DOI":"10.1021\/jf301998s","article-title":"Distribution of hydroxytyrosol and hydroxytyrosol acetate in olive oil emulsions and their antioxidant efficiency","volume":"60","author":"Albuquerque","year":"2012","journal-title":"J. Agric. Food Chem."},{"key":"ref_103","doi-asserted-by":"crossref","first-page":"296","DOI":"10.1002\/cphc.201500882","article-title":"A Physicochemical Study of the Effects of Acidity on the Distribution and Antioxidant Efficiency of Trolox in Olive Oil-in-Water Emulsions","volume":"17","author":"Galan","year":"2016","journal-title":"ChemPhysChem"},{"key":"ref_104","doi-asserted-by":"crossref","first-page":"3917","DOI":"10.1002\/jsfa.9615","article-title":"Control of antioxidant efficiency of chlorogenates in emulsions: Modulation of antioxidant interfacial concentrations","volume":"99","author":"Meireles","year":"2019","journal-title":"J. Sci. Food Agric."},{"key":"ref_105","doi-asserted-by":"crossref","first-page":"3266","DOI":"10.1021\/acs.jafc.8b06545","article-title":"Targeting Antioxidants to Interfaces: Control of the Oxidative Stability of Lipid-Based Emulsions","volume":"67","author":"Mitrus","year":"2019","journal-title":"J. Agric. Food Chem."},{"key":"ref_106","doi-asserted-by":"crossref","first-page":"564","DOI":"10.1002\/jsfa.7765","article-title":"Physical evidence that the variations in the efficiency of homologous series of antioxidants in emulsions are a result of differences in their distribution","volume":"97","author":"Costa","year":"2017","journal-title":"J. Sci. Food Agric."}],"container-title":["Antioxidants"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/2076-3921\/12\/4\/828\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T19:05:03Z","timestamp":1760123103000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/2076-3921\/12\/4\/828"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,3,28]]},"references-count":106,"journal-issue":{"issue":"4","published-online":{"date-parts":[[2023,4]]}},"alternative-id":["antiox12040828"],"URL":"https:\/\/doi.org\/10.3390\/antiox12040828","relation":{},"ISSN":["2076-3921"],"issn-type":[{"value":"2076-3921","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,3,28]]}}}