{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,2,6]],"date-time":"2026-02-06T23:08:38Z","timestamp":1770419318543,"version":"3.49.0"},"reference-count":46,"publisher":"MDPI AG","issue":"5","license":[{"start":{"date-parts":[[2021,5,10]],"date-time":"2021-05-10T00:00:00Z","timestamp":1620604800000},"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 a Tecnologia","doi-asserted-by":"publisher","award":["UIDB\/QUI\/50006\/2020"],"award-info":[{"award-number":["UIDB\/QUI\/50006\/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 a Tecnologia","doi-asserted-by":"publisher","award":["PTDC\/OCE-ETA\/32492\/2017\u2013POCI-01-0145-FEDER-032492"],"award-info":[{"award-number":["PTDC\/OCE-ETA\/32492\/2017\u2013POCI-01-0145-FEDER-032492"]}],"id":[{"id":"10.13039\/501100001871","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001871","name":"Funda\u00e7\u00e3o para a Ci\u00eancia e a Tecnologia","doi-asserted-by":"publisher","award":["SFRH\/BD\/100889\/2014"],"award-info":[{"award-number":["SFRH\/BD\/100889\/2014"]}],"id":[{"id":"10.13039\/501100001871","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001871","name":"Funda\u00e7\u00e3o para a Ci\u00eancia e a Tecnologia","doi-asserted-by":"publisher","award":["PTDC\/OCE- ETA\/32492\/2017"],"award-info":[{"award-number":["PTDC\/OCE- ETA\/32492\/2017"]}],"id":[{"id":"10.13039\/501100001871","id-type":"DOI","asserted-by":"publisher"}]},{"name":"INTERREG V-A Espanha-Portugal","award":["Programa IACOBUS"],"award-info":[{"award-number":["Programa IACOBUS"]}]},{"DOI":"10.13039\/501100010801","name":"Xunta de Galicia","doi-asserted-by":"publisher","award":["10TAL314003PR"],"award-info":[{"award-number":["10TAL314003PR"]}],"id":[{"id":"10.13039\/501100010801","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Foods"],"abstract":"<jats:p>Our previous research was focused on the effects of hydrophobicity on the antioxidant (AO) efficiency of series of homologous antioxidants with the same reactive moieties. In this work we evaluate the antioxidant efficiency of hydrophobic phenolipids in 4:6 olive oil-in-water emulsions, with different phenolic moieties (derived from caffeic, 4-hydroxycinnamic, dihydrocaffeic acids, tyrosol and hydroxytyrosol), with alkyl chains of 8 and 16 carbons, and compare the antioxidant efficiency with that of the parent compounds. All catecholic phenolipids, in particular the C8 derivatives, have proven to be better antioxidants for the oxidative protection of emulsions than their parental compounds with octyl dihydrocafffeate being the most efficient (16-fold increase in relation to the control). To understand the importance of some factors on the antioxidant efficiency of compounds in emulsions, Pearson\u2019s correlation analysis was carried out between antioxidant activity and the first anodic potential (Epa), reducing capacity (FRAP value), DPPH radical scavenging activity (EC50) and the concentration of antioxidants in each region of the emulsified system. Results confirm the importance of the effective concentration of AOs in the interfacial region (AOI) (\u03c1 = 0.820) and of the Epa (\u03c1 = \u22120.677) in predicting their antioxidant efficiency in olive oil-in-water emulsions.<\/jats:p>","DOI":"10.3390\/foods10051028","type":"journal-article","created":{"date-parts":[[2021,5,10]],"date-time":"2021-05-10T05:30:08Z","timestamp":1620624608000},"page":"1028","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":9,"title":["Effects of the Reactive Moiety of Phenolipids on Their Antioxidant Efficiency in Model Emulsified Systems"],"prefix":"10.3390","volume":"10","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-9614-409X","authenticated-orcid":false,"given":"Marlene","family":"Costa","sequence":"first","affiliation":[{"name":"REQUIMTE\/LAQV, Department of Chemistry and Biochemistry, Faculty of Sciences, University of Porto, Campo Alegre 687, 4169-007 Porto, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9447-5626","authenticated-orcid":false,"given":"Sonia","family":"Losada-Barreiro","sequence":"additional","affiliation":[{"name":"REQUIMTE\/LAQV, Department of Chemistry and Biochemistry, Faculty of Sciences, University of Porto, Campo Alegre 687, 4169-007 Porto, Portugal"},{"name":"Department of Physical-Chemistry, Faculty of Chemistry, Universidade de Vigo, 36310 Vigo, Spain"}]},{"given":"J\u00falia","family":"Magalh\u00e3es","sequence":"additional","affiliation":[{"name":"REQUIMTE\/LAQV, Department of Chemical Engineering, Faculty of Engineering, University of Porto, 4200-465 Porto, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7779-9250","authenticated-orcid":false,"given":"Lu\u00eds S.","family":"Monteiro","sequence":"additional","affiliation":[{"name":"Chemistry Centre, University of Minho, Gualtar, 4710-057 Braga, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9468-0881","authenticated-orcid":false,"given":"Carlos","family":"Bravo-D\u00edaz","sequence":"additional","affiliation":[{"name":"Department of Physical-Chemistry, Faculty of Chemistry, Universidade de Vigo, 36310 Vigo, Spain"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1149-6876","authenticated-orcid":false,"given":"F\u00e1tima","family":"Paiva-Martins","sequence":"additional","affiliation":[{"name":"REQUIMTE\/LAQV, Department of Chemistry and Biochemistry, Faculty of Sciences, University of Porto, Campo Alegre 687, 4169-007 Porto, Portugal"}]}],"member":"1968","published-online":{"date-parts":[[2021,5,10]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"R109","DOI":"10.1111\/j.1750-3841.2007.00507.x","article-title":"Emulsion-Based Delivery Systems for Lipophilic Bioactive Components","volume":"72","author":"McClements","year":"2007","journal-title":"J. Food Sci."},{"key":"ref_2","unstructured":"Frankel, E.N. (2014). Lipid Oxidation, Elsevier."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1016\/j.tifs.2010.11.003","article-title":"Mechanisms of lipid oxidation in food dispersions","volume":"22","author":"Waraho","year":"2011","journal-title":"Trends Food Sci. Technol."},{"key":"ref_4","doi-asserted-by":"crossref","unstructured":"Akoh, C.C. (2017). Food Lipids: Chemistry, Nutrition and Biotechnology, CRC Press.","DOI":"10.1201\/9781315151854"},{"key":"ref_5","doi-asserted-by":"crossref","unstructured":"Ferreira, I., Costa, M., Losada-Barreiro, S., Paiva-Martins, F., and Bravo-D\u00edaz, C. (2018). Modulating the interfacial concentration of gallates to improve the oxidative stability of fish oil-in-water emulsions. Food Res. Int., 112.","DOI":"10.1016\/j.foodres.2018.06.007"},{"key":"ref_6","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 \u201ccut-off\u201d effect","volume":"175","author":"Costa","year":"2015","journal-title":"Food Chem."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"11335","DOI":"10.1021\/jf9026266","article-title":"Chain Length Affects Antioxidant Properties of Chlorogenate Esters in Emulsion: The Cutoff Theory Behind the Polar Paradox","volume":"57","author":"Laguerre","year":"2009","journal-title":"J. Agric. Food Chem."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"12553","DOI":"10.1021\/jf500588s","article-title":"Antioxidant Properties and Efficacies of Synthesized Alkyl Caffeates, Ferulates, and Coumarates","volume":"62","author":"Durand","year":"2014","journal-title":"J. Agric. Food Chem."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"2869","DOI":"10.1021\/jf904119v","article-title":"Relationship between Hydrophobicity and Antioxidant Ability of \u201cPhenolipids\u201d in Emulsion: A Parabolic Effect of the Chain Length of Rosmarinate Esters","volume":"58","author":"Laguerre","year":"2010","journal-title":"J. Agric. Food Chem."},{"key":"ref_10","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."},{"key":"ref_11","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_12","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_13","doi-asserted-by":"crossref","first-page":"1600274","DOI":"10.1002\/ejlt.201600274","article-title":"Partitioning and antioxidative effect of protocatechuates in soybean oil emulsions: Relevance of emulsifier concentration","volume":"119","author":"Silva","year":"2017","journal-title":"Eur. J. Lipid Sci. Technol."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"212","DOI":"10.3390\/antiox3020212","article-title":"Distribution and antioxidant efficiency of resveratrol in stripped corn oil emulsions","volume":"3","author":"Costa","year":"2014","journal-title":"Antioxidants"},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"290","DOI":"10.1002\/poc.3196","article-title":"Distribution of catechol in emulsions","volume":"27","author":"Costa","year":"2014","journal-title":"J. Phys. Org. Chem."},{"key":"ref_16","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 \u2033Cut-off effect","volume":"61","author":"Romsted","year":"2013","journal-title":"J. Agric. Food Chem."},{"key":"ref_17","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_18","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_19","doi-asserted-by":"crossref","first-page":"303","DOI":"10.1016\/j.cis.2006.05.007","article-title":"Determining \u03b1-Tocopherol Distributions between the Oil, Water, and Interfacial Regions of Macroemulsions: Novel Applications of Electroanalytical Chemistry and the Pseudophase Kinetic Model","volume":"123","author":"Gunaseelan","year":"2006","journal-title":"Adv. Colloid Interface Sci."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"933","DOI":"10.1016\/0891-5849(95)02227-9","article-title":"Structure-antioxidant activity relationships of flavonoids and phenolic acids","volume":"20","author":"Miller","year":"1996","journal-title":"Free Radic. Biol. Med."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"15","DOI":"10.1016\/S0076-6879(99)99005-5","article-title":"Ferric Reducing\/Antioxidant Power Assay: Direct Measure of Total Antioxidant Activity of Biological Fluids and Modified Version for Simultaneous Measurement of Total Antioxidant Power and Ascorbic Acid Concentration","volume":"Volume 299","author":"Benzie","year":"1999","journal-title":"Methods in Enzymology"},{"key":"ref_22","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_23","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_24","doi-asserted-by":"crossref","first-page":"359","DOI":"10.1016\/j.pedneo.2018.07.012","article-title":"Effects of two different lipid emulsions on antioxidant status, lipid peroxidation and parenteral nutrition-related cholestasis in premature babies, a randomized-controlled study","volume":"60","author":"Yildizdas","year":"2019","journal-title":"Pediatr. Neonatol."},{"key":"ref_25","doi-asserted-by":"crossref","unstructured":"Mollica, F., Lucarini, M., Passerini, C., Carati, C., Pavoni, S., Bonoldi, L., and Amorati, R. (2020). Effect of Antioxidants on High-Temperature Stability of Renewable Bio-Oils Revealed by an Innovative Method for the Determination of Kinetic Parameters of Oxidative Reactions. Antioxidants, 9.","DOI":"10.3390\/antiox9050399"},{"key":"ref_26","doi-asserted-by":"crossref","unstructured":"Bibi Sadeer, N., Montesano, D., Albrizio, S., Zengin, G., and Mahomoodally, M.F. (2020). The Versatility of Antioxidant Assays in Food Science and Safety\u2014Chemistry, Applications, Strengths, and Limitations. Antioxidants, 9.","DOI":"10.3390\/antiox9080709"},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"2122","DOI":"10.1021\/jf9913110","article-title":"Phenolic Acids and Derivatives:\u2009 Studies on the Relationship among Structure, Radical Scavenging Activity, and Physicochemical Parameters","volume":"48","author":"Silva","year":"2000","journal-title":"J. Agric. Food Chem."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"433","DOI":"10.1080\/10715760500540442","article-title":"Antioxidant profile of dihydroxy-and trihydroxyphenolic acids-A structure\u2013activity relationship study","volume":"40","author":"Siquet","year":"2006","journal-title":"Free Radic. Res."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"243","DOI":"10.1179\/135100001101536391","article-title":"Antioxidant capacity of phenolic and related compounds: Correlation among electrochemical, visible spectroscopy methods and structure\u2013antioxidant activity","volume":"6","author":"Galato","year":"2001","journal-title":"Redox Rep."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"2275","DOI":"10.1002\/elan.200704004","article-title":"Direct electrochemical sensing and detection of natural antioxidants and antioxidant capacity in vitro systems","volume":"19","author":"Blasco","year":"2007","journal-title":"Electroanalysis"},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"2866","DOI":"10.1021\/jf026182t","article-title":"Phenolic Acids in Foods:\u2009 An Overview of Analytical Methodology","volume":"51","author":"Robbins","year":"2003","journal-title":"J. Agric. Food Chem."},{"key":"ref_32","doi-asserted-by":"crossref","unstructured":"Rappoport, Z. (2003). Phenols as Antioxidants. The Chemistry of Phenols, John Wiley & Sons, Ltd.","DOI":"10.1002\/0470857277"},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"222","DOI":"10.1021\/ar0682029","article-title":"Solvent Effects on the Rates and Mechanisms of Reaction of Phenols with Free Radicals","volume":"40","author":"Litwinienko","year":"2007","journal-title":"Acc. Chem. Res."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"288","DOI":"10.1016\/j.foodchem.2010.08.012","article-title":"The molecular basis of working mechanism of natural polyphenolic antioxidants","volume":"125","author":"Leopoldini","year":"2011","journal-title":"Food Chem."},{"key":"ref_35","doi-asserted-by":"crossref","unstructured":"Dangles, O., Dufour, C., Tonnel\u00e9, C., and Trouillas, P. (2017). The Physical Chemistry of Polyphenols. Recent Adv. Polyphen. Res., 1\u201335.","DOI":"10.1002\/9781118883303.ch1"},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"1680","DOI":"10.1111\/1541-4337.12566","article-title":"Natural phenolic antioxidants electrochemistry: Towards a new food science methodology","volume":"19","author":"Enache","year":"2020","journal-title":"Compr. Rev. Food Sci. Food Saf."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"8703","DOI":"10.1021\/ac101854w","article-title":"How do phenolic compounds react toward superoxide ion? A simple electrochemical method for evaluating antioxidant capacity","volume":"82","author":"Rene","year":"2010","journal-title":"Anal. Chem."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"5816","DOI":"10.1016\/j.bmc.2010.06.090","article-title":"Lipophilic phenolic antioxidants: Correlation between antioxidant profile, partition coefficients and redox properties","volume":"18","author":"Roleira","year":"2010","journal-title":"Bioorg. Med. Chem."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"961","DOI":"10.1016\/j.biochi.2011.12.015","article-title":"Alkyl esters of hydroxycinnamic acids with improved antioxidant activity and lipophilicity protect PC12 cells against oxidative stress","volume":"94","author":"Garrido","year":"2012","journal-title":"Biochimie"},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"2309","DOI":"10.1021\/jo035758q","article-title":"Electron-Transfer Reaction of Cinnamic Acids and Their Methyl Esters with the DPPH\u2022 Radical in Alcoholic Solutions","volume":"69","author":"Foti","year":"2004","journal-title":"J. Org. Chem."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"5763","DOI":"10.1021\/jf060132x","article-title":"Structure\u2212DPPH\u2022 scavenging activity relationships: Parallel study of catechol and guaiacol acid derivatives","volume":"54","author":"Ordoudi","year":"2006","journal-title":"J. Agric. Food Chem."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"405","DOI":"10.1016\/0891-5849(87)90019-0","article-title":"Free radicals in iron-containing systems","volume":"3","author":"Dunford","year":"1987","journal-title":"Free Radic. Biol. Med."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"571","DOI":"10.1007\/s11746-002-0524-4","article-title":"Effects of pH and ferric ions on the antioxidant activity of olive polyphenols in oil-in-water emulsions","volume":"79","author":"Gordon","year":"2002","journal-title":"J. Am. Oil Chem. Soc."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"2704","DOI":"10.1021\/jf0481094","article-title":"Interactions of Ferric Ions with Olive Oil Phenolic Compounds","volume":"53","author":"Gordon","year":"2005","journal-title":"J. Agric. Food Chem."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"10297","DOI":"10.1021\/jf503543x","article-title":"Synthesis and antioxidant activity of nitrohydroxytyrosol and its acyl derivatives","volume":"62","author":"Trujillo","year":"2014","journal-title":"J. Agric. Food Chem."},{"key":"ref_46","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."}],"container-title":["Foods"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/2304-8158\/10\/5\/1028\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T05:58:35Z","timestamp":1760162315000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/2304-8158\/10\/5\/1028"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,5,10]]},"references-count":46,"journal-issue":{"issue":"5","published-online":{"date-parts":[[2021,5]]}},"alternative-id":["foods10051028"],"URL":"https:\/\/doi.org\/10.3390\/foods10051028","relation":{},"ISSN":["2304-8158"],"issn-type":[{"value":"2304-8158","type":"electronic"}],"subject":[],"published":{"date-parts":[[2021,5,10]]}}}