{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,2,10]],"date-time":"2026-02-10T13:50:30Z","timestamp":1770731430190,"version":"3.49.0"},"reference-count":79,"publisher":"MDPI AG","issue":"5","license":[{"start":{"date-parts":[[2024,5,11]],"date-time":"2024-05-11T00:00:00Z","timestamp":1715385600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"University of Vigo","award":["PID2022-136443OB-I00"],"award-info":[{"award-number":["PID2022-136443OB-I00"]}]},{"name":"University of Vigo","award":["MICIU\/AEI\/10.13039\/501100011033"],"award-info":[{"award-number":["MICIU\/AEI\/10.13039\/501100011033"]}]},{"name":"University of Vigo","award":["FCT\/MCTES (UIDB\/QUI\/50006\/2020)"],"award-info":[{"award-number":["FCT\/MCTES (UIDB\/QUI\/50006\/2020)"]}]},{"name":"University of Vigo","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"]}]},{"name":"ERDF\/EU","award":["PID2022-136443OB-I00"],"award-info":[{"award-number":["PID2022-136443OB-I00"]}]},{"name":"ERDF\/EU","award":["MICIU\/AEI\/10.13039\/501100011033"],"award-info":[{"award-number":["MICIU\/AEI\/10.13039\/501100011033"]}]},{"name":"ERDF\/EU","award":["FCT\/MCTES (UIDB\/QUI\/50006\/2020)"],"award-info":[{"award-number":["FCT\/MCTES (UIDB\/QUI\/50006\/2020)"]}]},{"name":"ERDF\/EU","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"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Antioxidants"],"abstract":"<jats:p>In this work, we aim to find physical evidence demonstrating the crucial role that the effective concentration of antioxidants (AOs) present at the interfacial region of emulsions has in controlling the inhibition of the lipid oxidation reaction. We prepared a series of antioxidants of different hydrophobicities derived from chlorogenic and protocatechuic acids. We first monitored, in intact emulsions, the (sigmoidal) production of conjugated dienes and determined the corresponding induction times, tind. Independently, we determined the effective concentrations of the antioxidants in the same intact emulsions. Results show that both the length of the induction periods and the antioxidant interfacial concentrations parallel each other, with a maximum at the octyl-dodecyl derivatives. The ratio between the interfacial antioxidant concentrations and the induction periods remains constant for all AOs in the same series, so that the rates of initiation of lipid oxidation are the same regardless of the hydrophobicity of the antioxidant employed. The constancy in the rate of initiation provides strong experimental evidence for a direct relationship between interfacial concentrations and antioxidant efficiencies. Results suggest new possibilities to investigate lipid peroxidation under non-forced conditions and are of interest to formulators interested in preparing emulsions with antimicrobial properties.<\/jats:p>","DOI":"10.3390\/antiox13050593","type":"journal-article","created":{"date-parts":[[2024,5,14]],"date-time":"2024-05-14T08:59:37Z","timestamp":1715677177000},"page":"593","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":8,"title":["Analysis of the Efficiency of Antioxidants in Inhibiting Lipid Oxidation in Terms of Characteristic Kinetic Parameters"],"prefix":"10.3390","volume":"13","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-9447-5626","authenticated-orcid":false,"given":"Sonia","family":"Losada-Barreiro","sequence":"first","affiliation":[{"name":"Departamento de Qu\u00edmica-F\u00edsica, Facultad de Qu\u00edmica, 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, 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 de Qu\u00edmica-F\u00edsica, Facultad de Qu\u00edmica, Universidade de Vigo, 36310 Vigo, Spain"}]}],"member":"1968","published-online":{"date-parts":[[2024,5,11]]},"reference":[{"key":"ref_1","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_2","doi-asserted-by":"crossref","first-page":"401","DOI":"10.1016\/j.ajps.2017.05.003","article-title":"Lipid Peroxidation: Its Effects on the Formulation and Use of Pharmaceutical Emulsions","volume":"12","author":"Khanum","year":"2017","journal-title":"Asian J. Pharm. Sci."},{"key":"ref_3","unstructured":"Fennema, O.R. (2007). Food Chemistry, CRC Press. [4th ed.]."},{"key":"ref_4","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_5","doi-asserted-by":"crossref","first-page":"4250","DOI":"10.1111\/1541-4337.12792","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":"Compr. Rev. Food Sci. Food Saf."},{"key":"ref_6","unstructured":"Shahidi, F. (2020). Bailey\u2019s Industrial Oil and Fat Products, Wiley."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"461","DOI":"10.1080\/10408398.2018.1538931","article-title":"Food Lipid Oxidation under Gastrointestinal Digestion Conditions: A Review","volume":"60","author":"Goicoechea","year":"2020","journal-title":"Crit. Rev. Food Sci. Nutr."},{"key":"ref_8","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_9","doi-asserted-by":"crossref","unstructured":"Mansoor, S., Ali Wani, O., Lone, J.K., Manhas, S., Kour, N., Alam, P., Ahmad, A., and Ahmad, P. (2022). Reactive Oxygen Species in Plants: From Source to Sink. Antioxidants, 11.","DOI":"10.3390\/antiox11020225"},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"7343","DOI":"10.1039\/D1CS00265A","article-title":"Autoxidation vs. Antioxidants\u2014The Fight for Forever","volume":"50","author":"Helberg","year":"2021","journal-title":"Chem. Soc. Rev."},{"key":"ref_11","first-page":"100107","article-title":"Co-Delivery of Synergistic Antioxidants from Food Sources for the Prevention of Oxidative Stress","volume":"3","author":"Fleming","year":"2021","journal-title":"J. Agric. Food Res."},{"key":"ref_12","doi-asserted-by":"crossref","unstructured":"Frankel, E. (2005). Lipid Oxidation, The Oily Press, PJ Barnes & Associates.","DOI":"10.1533\/9780857097927"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"2300067","DOI":"10.1002\/ejlt.202300067","article-title":"Interlaboratory Study on Lipid Oxidation During Accelerated Storage Trials with Rapeseed and Sunflower Oil Analyzed by Conjugated Dienes as Primary Oxidation Products","volume":"125","author":"Amft","year":"2023","journal-title":"Eur. J. Lipid Sci. Technol."},{"key":"ref_14","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\u201d","volume":"61","author":"Romsted","year":"2013","journal-title":"J. Agric. Food Chem."},{"key":"ref_15","doi-asserted-by":"crossref","unstructured":"Liang, N., and Kitts, D.D. (2015). Role of Chlorogenic Acids in Controlling Oxidative and Inflammatory Stress Conditions. Nutrients, 8.","DOI":"10.3390\/nu8010016"},{"key":"ref_16","unstructured":"Martin, C.R., Patel, V.B., and Preedy, V.R. (2023). Treatments, Nutraceuticals, Supplements, and Herbal Medicine in Neurological Disorders, Academic Press."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"105109","DOI":"10.1016\/j.phrs.2020.105109","article-title":"New Progress in the Pharmacology of Protocatechuic Acid: A Compound Ingested in Daily Foods and Herbs Frequently and Heavily","volume":"161","author":"Song","year":"2020","journal-title":"Pharmacol. Res."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"4931","DOI":"10.1111\/ijfs.16617","article-title":"Recent Advance in the Biological Activity of Chlorogenic Acid and Its Application in Food Industry","volume":"58","author":"Li","year":"2023","journal-title":"Int. J. Food Sci. Technol."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"593902","DOI":"10.1155\/2015\/593902","article-title":"Pharmacological Properties of Protocatechuic Acid and Its Potential Roles as Complementary Medicine","volume":"2015","author":"Semaming","year":"2015","journal-title":"Evid.-Based Complement. Altern. Med."},{"key":"ref_20","doi-asserted-by":"crossref","unstructured":"Hu, R., He, Z., Liu, M., Tan, J., Zhang, H., Hou, D.-X., He, J., and Wu, S. (2020). Dietary Protocatechuic Acid Ameliorates Inflammation and up-Regulates Intestinal Tight Junction Proteins by Modulating Gut Microbiota in Lps-Challenged Piglets. J. Anim. Sci. Biotechnol., 11.","DOI":"10.1186\/s40104-020-00492-9"},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"9022","DOI":"10.1021\/cr500226n","article-title":"Advances in Radical-Trapping Antioxidant Chemistry in the 21st Century: A Kinetics and Mechanisms Perspective","volume":"114","author":"Ingold","year":"2014","journal-title":"Chem. Rev."},{"key":"ref_22","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_23","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_24","doi-asserted-by":"crossref","first-page":"45","DOI":"10.1073\/pnas.90.1.45","article-title":"Autoxidation of Lipids and Antioxidation by Alpha-Tocopherol and Ubiquinol in Homogeneous Solution and in Aqueous Dispersions of Lipids: Unrecognized Consequences of Lipid Particle Size as Exemplified by Oxidation of Human Low Density Lipoprotein","volume":"90","author":"Ingold","year":"1993","journal-title":"Proc. Natl. Acad. Sci. USA"},{"key":"ref_25","unstructured":"Schaich, K.M., Shahidi, F., Zhong, Y., and Eskin, N.A.M. (2013). Biochemistry of Foods, Academic Press. [3rd ed.]."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"750","DOI":"10.1021\/acs.jafc.0c06209","article-title":"Impact of Polyunsaturated Fatty Acid Dilution and Antioxidant Addition on Lipid Oxidation Kinetics in Oil\/Water Emulsions","volume":"69","author":"Culler","year":"2021","journal-title":"J. Agric. Food Chem."},{"key":"ref_27","doi-asserted-by":"crossref","unstructured":"Rappoport, Z. (2003). The Chemistry of Phenols, John Wiley & Sons.","DOI":"10.1002\/0470857277"},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"6252","DOI":"10.1080\/10408398.2022.2029827","article-title":"Advances in the Control of Lipid Peroxidation in Oil-in-Water Emulsions: Kinetic Approaches","volume":"63","year":"2023","journal-title":"Crit. Rev. Food Sci. Nutr."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"63","DOI":"10.1016\/j.chemphyslip.2013.12.001","article-title":"Analysis of the Kinetics of Lipid Peroxidation in Terms of Characteristic Time-Points","volume":"178","author":"Pinchuk","year":"2014","journal-title":"Chem. Phys. Lipids"},{"key":"ref_30","doi-asserted-by":"crossref","unstructured":"Shahidi, F. (2005). Bailey\u2019s Industrial Oil and Fat Products, Wiley & Sons.","DOI":"10.1002\/047167849X"},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"137274","DOI":"10.1016\/j.foodchem.2023.137274","article-title":"Antioxidant Efficiency and Oxidizability of Mayonnaise by Oximetry and Isothermal Calorimetry","volume":"433","author":"Suhag","year":"2024","journal-title":"Food Chem."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"248","DOI":"10.1016\/j.jcis.2021.06.101","article-title":"Interfacial Kinetics in Olive Oil-in-Water Nanoemulsions: Relationships between Rates of Initiation of Lipid Peroxidation, Induction Times and Effective Interfacial Antioxidant Concentrations","volume":"604","author":"Costa","year":"2021","journal-title":"J. Colloid Interface Sci."},{"key":"ref_33","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_34","doi-asserted-by":"crossref","unstructured":"Apak, R., Capanoglu, E., and Shahidi, F. (2018). Measurement of Antioxidant Activity & Capacity: Recent Trends and Applications, Wiley & Sons.","DOI":"10.1002\/9781119135388"},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"954","DOI":"10.1021\/tx960057s","article-title":"Radical-Initiated Lipid Peroxidation in Low Density Lipoproteins:\u2009 Insights Obtained from Kinetic Modeling","volume":"9","author":"Waldeck","year":"1996","journal-title":"Chem. Res. Toxicol."},{"key":"ref_36","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 Colloidss","volume":"32","author":"Dar","year":"2017","journal-title":"Curr. Opin. Colloid Interface Sci."},{"key":"ref_37","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_38","doi-asserted-by":"crossref","first-page":"127088","DOI":"10.1016\/j.foodchem.2020.127088","article-title":"A Reconsidered Approach Providing Kinetic Parameters and Rate Constants to Analyze the Oxidative Stability of Bulk Lipid Systems","volume":"327","author":"Farhoosh","year":"2020","journal-title":"Food Chem."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"288","DOI":"10.1016\/j.foodchem.2018.12.020","article-title":"The Location of Amphiphobic Antioxidants in Micellar Systems: The Diving-Swan Analogy","volume":"279","author":"Rezende","year":"2019","journal-title":"Food Chem."},{"key":"ref_40","first-page":"1270","article-title":"Lipid Oxidation in Oil-in-Water Emulsions: Impact of Molecular Environment on Chemical Reactions in Heterogeneous Food Systems","volume":"65","author":"McClements","year":"2000","journal-title":"JFS Concise Rev. Food Sci."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"391","DOI":"10.1146\/annurev-food-030216-025812","article-title":"Mass Transport Phenomena in Lipid Oxidation and Antioxidation","volume":"8","author":"Laguerre","year":"2017","journal-title":"Annu. Rev. Food Sci. Technol."},{"key":"ref_42","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_43","doi-asserted-by":"crossref","first-page":"1600277","DOI":"10.1002\/ejlt.201600277","article-title":"Using a Pseudophase Model to Determine AO Distributions in Emulsions: Why Dynamic Equilibrium Matters","volume":"119","author":"Romsted","year":"2017","journal-title":"Eur. J. Lipid Sci. Technol."},{"key":"ref_44","doi-asserted-by":"crossref","unstructured":"Costa, M., Paiva-Martins, F., Losada-Barreiro, S., and Bravo-D\u00edaz, C. (2021). Modeling Chemical Reactivity at the Interfaces of Emulsions: Effects of Partitioning and Temperature. Molecules, 26.","DOI":"10.3390\/molecules26154703"},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"294","DOI":"10.1016\/j.jcis.2008.02.042","article-title":"The Partitioning of Emulsifiers in O\/W Emulsions: A Comparative Study of Sans, Ultrafiltration and Dialysis","volume":"322","author":"Oehlke","year":"2008","journal-title":"J. Colloid Interface Sci."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"561","DOI":"10.1007\/s11745-007-3053-5","article-title":"Investigating the Location of Propyl Gallate at Surfaces and Its Chemical Microenvironment by 1H NMR","volume":"42","author":"Heins","year":"2007","journal-title":"Lipids"},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"535","DOI":"10.1007\/s11746-000-0085-6","article-title":"The Influence of Various Emulsifiers on the Partitioning and Antioxidant Activity of Hydrobenzoic acids and Their Derivatives in Oil-in-Water Emulsions","volume":"77","author":"Schwarz","year":"2000","journal-title":"J. Am. Oil Chem. Soc."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"1600276","DOI":"10.1002\/ejlt.201600276","article-title":"Alkyl Caffeates as Antioxidants in O\/W Emulsions: Impact of Emulsifier Type and Endogenous Tocopherols","volume":"119","author":"Villeneuve","year":"2017","journal-title":"Eur. J. Lipid Sci. Technol."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"1991","DOI":"10.1021\/jf9701695","article-title":"Partition of Selected Antioxidants in Corn Oil-Water Model Systems","volume":"45","author":"Huang","year":"1997","journal-title":"J. Agric. Food Chem."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"3601","DOI":"10.1021\/jf990097c","article-title":"Partitioning of Selected Antioxidants in Mayonnaise","volume":"47","author":"Jacobsen","year":"1999","journal-title":"J. Agric. Food. Chem."},{"key":"ref_51","doi-asserted-by":"crossref","unstructured":"Costa, M., Losada-Barreiro, S., Paiva-Martins, F., and Bravo-D\u00edaz, C. (2021). Polyphenolic Antioxidants in Lipid Emulsions: Partitioning Effects and Interfacial Phenomena. Foods, 10.","DOI":"10.3390\/foods10030539"},{"key":"ref_52","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_53","doi-asserted-by":"crossref","first-page":"1572","DOI":"10.1021\/jo01323a048","article-title":"Alkyl-Nitrite-Metal Halide Deamination Reactions. 6. Direct Synthesis of Arene Diazonium Tetrafluorborates Salts from Aromatic Amines, ter-Butyl Nitrite and Borom Trifluoride Ethearate in Anhydrous Media","volume":"44","author":"Doyle","year":"1979","journal-title":"J. Org. Chem."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"2480","DOI":"10.1021\/jf000537w","article-title":"Antioxidant Activity of Hydroxytyrosol Acetate Compared to That of Other Olive Oil Polyphenols","volume":"49","author":"Gordon","year":"2001","journal-title":"J. Agric. Food. Chem."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"127509","DOI":"10.1016\/j.foodchem.2020.127509","article-title":"When Polyphenols Meet Lipids: Challenges in Membrane Biophysics and Opportunities in Epithelial Lipidomics","volume":"333","author":"Reis","year":"2020","journal-title":"Food Chem."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"1579","DOI":"10.1007\/s00580-015-2119-7","article-title":"Antioxidant and Antidiabetic Effects of Gallic and Protocatechuic Acids: A Structure\u2013Function Perspective","volume":"24","author":"Adefegha","year":"2015","journal-title":"Comp. Clin. Pathol."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"952943","DOI":"10.1155\/2014\/952943","article-title":"A Review on Protocatechuic Acid and Its Pharmacological Potential","volume":"2014","author":"Kakkar","year":"2014","journal-title":"ISRN Pharmacol."},{"key":"ref_58","unstructured":"Stalmach, A. (2014). Polyphenols in Human Health and Disease, Academic Press."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"6986","DOI":"10.1021\/jf100569j","article-title":"Structure\u2013Property\u2013Activity Relationship of Phenolic Acids and Derivatives. Protocatechuic Acid Alkyl Esters","volume":"58","author":"Reis","year":"2010","journal-title":"J. Agric. Food Chem."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"11052","DOI":"10.1021\/jf072586f","article-title":"Ability of Surface-Active Antioxidants to Inhibit Lipid Oxidation in Oil-in-Water Emulsion","volume":"55","author":"Yuji","year":"2007","journal-title":"J. Agric. Food Chem."},{"key":"ref_61","doi-asserted-by":"crossref","unstructured":"Costa, M., Losada-Barreiro, S., Vicente, A., Bravo-D\u00edaz, C., and Paiva-Martins, F. (2022). Unexpected Antioxidant Efficiency of Chlorogenic Acid Phenolipids in Fish Oil-in-Water Nanoemulsions: An Example of How Relatively Low Interfacial Concentrations Can Make Antioxidants to Be Inefficient. Molecules, 27.","DOI":"10.3390\/molecules27030861"},{"key":"ref_62","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_63","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_64","doi-asserted-by":"crossref","first-page":"11335","DOI":"10.1021\/jf9026266","article-title":"Chain Length Affects Antioxidant Properties of Chlorogenate Esters in Emulsion: The Cut-Off Theory Behind the Polar Paradox","volume":"57","author":"Laguerre","year":"2009","journal-title":"J. Agric. Food Chem"},{"key":"ref_65","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 Lenght of Rosmarinate Esters","volume":"58","author":"Laguerre","year":"2010","journal-title":"J. Agric. Food Chem."},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"10960","DOI":"10.1021\/jf8020267","article-title":"New Lipophilic Tyrosyl Esters. Comparative Antioxidant Evaluation with Hydroxytyrosyl Esters","volume":"53","author":"Mateos","year":"2008","journal-title":"J. Agric. Food Chem."},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"9773","DOI":"10.1021\/jf9023867","article-title":"Effect of Lipophilization of Hydroxytyrosol on Its Antioxidant Activity in Fish Oils and Fish Oil-in-Water Emulsions","volume":"57","author":"Medina","year":"2009","journal-title":"J. Agric. Food Chem."},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"945","DOI":"10.1111\/1541-4337.12097","article-title":"Lipid Oxidation in Oil-in-Water Emulsions: Involvement of the Interfacial Layer","volume":"13","author":"Ropers","year":"2014","journal-title":"Compr. Rev. Food Sci. Food Safety"},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"5052","DOI":"10.1021\/jf200086n","article-title":"Contribution of the interfacial layer to the protection of emulsified lipids against oxidation","volume":"59","author":"Berton","year":"2011","journal-title":"J. Agric. Food Chem."},{"key":"ref_70","unstructured":"Kahveci, D., Laguerre, M., and Villeneuve, P. (2015). Polar Lipids, Elsevier."},{"key":"ref_71","doi-asserted-by":"crossref","first-page":"3233","DOI":"10.1021\/ja01617a026","article-title":"Air Oxidation of Hydrocarbons.1 II. The Stoichiometry and Fate of Inhibitors in Benzene and Chlorobenzene","volume":"77","author":"Boozer","year":"1955","journal-title":"J. Am. Chem. Soc."},{"key":"ref_72","first-page":"863","article-title":"Kinetic and Stoichiometry of the Reaction of Chlorogenic Acid and Its Alkyl Esters against the DPPH Radical","volume":"57","author":"Laguerre","year":"2011","journal-title":"J. Agric. Food Chem."},{"key":"ref_73","doi-asserted-by":"crossref","first-page":"230","DOI":"10.1016\/j.talanta.2006.03.050","article-title":"Radical Scavenging Ability of Polyphenolic Compounds Towards Dpph Free Radical","volume":"71","author":"Troncoso","year":"2007","journal-title":"Talanta"},{"key":"ref_74","doi-asserted-by":"crossref","first-page":"7621","DOI":"10.1038\/s41598-023-34382-7","article-title":"A Kinetic-Based Stopped-Flow Dpph\u2022 Method","volume":"13","author":"Angeli","year":"2023","journal-title":"Sci. Rep."},{"key":"ref_75","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_76","doi-asserted-by":"crossref","first-page":"1221","DOI":"10.1271\/bbb.68.1221","article-title":"Effects of Alcoholic Solvents on Antiradical Abilities of Protocatechuic Acid and Its Alkyl Esters","volume":"68","author":"Saito","year":"2004","journal-title":"Biosci. Biotechnol. Biochem."},{"key":"ref_77","doi-asserted-by":"crossref","first-page":"1713","DOI":"10.1246\/bcsj.69.1713","article-title":"Comparison of the Efficiencies of the Fused Heterocyclic Compounds, 9h-Xanthene-2,7-Diols, and Related Chain-Breaking Phenolic Antioxidants","volume":"69","author":"Yamamura","year":"1996","journal-title":"Bull. Chem. Soc. Jpn."},{"key":"ref_78","doi-asserted-by":"crossref","first-page":"5888","DOI":"10.1021\/jo049254j","article-title":"Abnormal Solvent Effects on Hydrogen Atom Abstraction. 2. Resolution of the Curcumin Antioxidant Controversy. The Role of Sequential Proton Loss Electron Transfer","volume":"69","author":"Litwinienko","year":"2004","journal-title":"J. Org. Chem."},{"key":"ref_79","doi-asserted-by":"crossref","first-page":"551","DOI":"10.1146\/annurev-food-030117-012405","article-title":"Formation, Structure, and Functionality of Interfacial Layers in Food Emulsions","volume":"9","author":"Sagis","year":"2018","journal-title":"Annu. Rev. Food Sci. Technol."}],"container-title":["Antioxidants"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/2076-3921\/13\/5\/593\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T14:40:54Z","timestamp":1760107254000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/2076-3921\/13\/5\/593"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,5,11]]},"references-count":79,"journal-issue":{"issue":"5","published-online":{"date-parts":[[2024,5]]}},"alternative-id":["antiox13050593"],"URL":"https:\/\/doi.org\/10.3390\/antiox13050593","relation":{},"ISSN":["2076-3921"],"issn-type":[{"value":"2076-3921","type":"electronic"}],"subject":[],"published":{"date-parts":[[2024,5,11]]}}}