{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,2]],"date-time":"2026-07-02T11:02:06Z","timestamp":1782990126781,"version":"3.54.5"},"reference-count":55,"publisher":"MDPI AG","issue":"5","license":[{"start":{"date-parts":[[2025,5,13]],"date-time":"2025-05-13T00:00:00Z","timestamp":1747094400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Ministerio de Ciencia, Innovaci\u00f3n y Universidades (MICIN)","award":["PID2021-125259OB-I00"],"award-info":[{"award-number":["PID2021-125259OB-I00"]}]},{"name":"Ministerio de Ciencia, Innovaci\u00f3n y Universidades (MICIN)","award":["PID2021-125259OB-I00"],"award-info":[{"award-number":["PID2021-125259OB-I00"]}]},{"name":"Ministerio de Ciencia, Innovaci\u00f3n y Universidades (MICIN)","award":["PRE2022-105658"],"award-info":[{"award-number":["PRE2022-105658"]}]},{"name":"Ministerio de Ciencia, Innovaci\u00f3n y Universidades (MICIN)","award":["PRE2022-102252"],"award-info":[{"award-number":["PRE2022-102252"]}]},{"name":"Agencia Estatal de Investigaci\u00f3n (AEI)","award":["PID2021-125259OB-I00"],"award-info":[{"award-number":["PID2021-125259OB-I00"]}]},{"name":"Agencia Estatal de Investigaci\u00f3n (AEI)","award":["PID2021-125259OB-I00"],"award-info":[{"award-number":["PID2021-125259OB-I00"]}]},{"name":"Agencia Estatal de Investigaci\u00f3n (AEI)","award":["PRE2022-105658"],"award-info":[{"award-number":["PRE2022-105658"]}]},{"name":"Agencia Estatal de Investigaci\u00f3n (AEI)","award":["PRE2022-102252"],"award-info":[{"award-number":["PRE2022-102252"]}]},{"name":"MICIN\/AEI","award":["PID2021-125259OB-I00"],"award-info":[{"award-number":["PID2021-125259OB-I00"]}]},{"name":"MICIN\/AEI","award":["PID2021-125259OB-I00"],"award-info":[{"award-number":["PID2021-125259OB-I00"]}]},{"name":"MICIN\/AEI","award":["PRE2022-105658"],"award-info":[{"award-number":["PRE2022-105658"]}]},{"name":"MICIN\/AEI","award":["PRE2022-102252"],"award-info":[{"award-number":["PRE2022-102252"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Biomolecules"],"abstract":"<jats:p>Hydroxytyrosol (HT), the primary phenolic compound in virgin olive oil, has notable cardiovascular benefits, particularly in preventing low-density lipoprotein (LDL) oxidation. However, its hydrophilicity limits its solubility and integration into lipid-based formulations. This study aimed to enhance its lipophilicity by synthesizing hydroxytyrosyl eicosapentaenoate (HT-EPA), a derivative of HT and eicosapentaenoic acid (EPA), using a one-step enzymatic catalysis with lipase B from Candida antarctica (CALB). The reaction, performed as a suspension of HT in ethyl eicosapentaenoate (Et-EPA) (1:9 molar ratio) under vacuum, achieved higher yields and shorter reaction times than previously reported, with a purity exceeding 98%, confirmed by 1H-NMR. For the first time, the antioxidant capacity of HT-EPA in comparison with other natural antioxidants was assessed using the FRAP assay, while its oxidative stability in an omega-3-rich oil matrix was evaluated via the Rancimat method. HT-EPA and hydroxytyrosyl acetate (HT-Ac) displayed antioxidant activity comparable to HT but significantly higher than \u03b1-tocopherol, a common food antioxidant. Given the scarcity of effective lipid-soluble antioxidants, HT-EPA represents a promising candidate for omega-3 nutraceuticals, offering enhanced stability and potential health benefits. This study provides a simple, efficient, and scalable strategy for developing functional lipid-based formulations with cardioprotective potential by improving HT solubility while preserving its antioxidant properties.<\/jats:p>","DOI":"10.3390\/biom15050714","type":"journal-article","created":{"date-parts":[[2025,5,13]],"date-time":"2025-05-13T09:26:48Z","timestamp":1747128408000},"page":"714","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Hydroxytyrosyl Eicosapentaenoate as a Potential Antioxidant for Omega-3 Fatty Acids: Improved Synthesis and Comparative Evaluation with Other Natural Antioxidants"],"prefix":"10.3390","volume":"15","author":[{"ORCID":"https:\/\/orcid.org\/0009-0004-1862-2358","authenticated-orcid":false,"given":"Natalia","family":"Garc\u00eda-Acosta","sequence":"first","affiliation":[{"name":"Department of Metabolism and Nutrition (DMN), Institute of Food Science, Food Technology, and Nutrition (ICTAN), Spanish National Research Council (CSIC), C\/Jos\u00e9 Antonio Novais 6, 28040 Madrid, Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3972-6522","authenticated-orcid":false,"given":"Rosa","family":"Cert","sequence":"additional","affiliation":[{"name":"Fat Institute, Spanish National Research Council (CSIC), Universidad Pablo d Olavide, Edificio 46 Ctra. De Utrera Km 1, 41013 Seville, Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Marta","family":"Jord\u00e1n","sequence":"additional","affiliation":[{"name":"Department of Metabolism and Nutrition (DMN), Institute of Food Science, Food Technology, and Nutrition (ICTAN), Spanish National Research Council (CSIC), C\/Jos\u00e9 Antonio Novais 6, 28040 Madrid, Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Luis","family":"Goya","sequence":"additional","affiliation":[{"name":"Department of Metabolism and Nutrition (DMN), Institute of Food Science, Food Technology, and Nutrition (ICTAN), Spanish National Research Council (CSIC), C\/Jos\u00e9 Antonio Novais 6, 28040 Madrid, Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9722-1939","authenticated-orcid":false,"given":"Raquel","family":"Mateos","sequence":"additional","affiliation":[{"name":"Department of Metabolism and Nutrition (DMN), Institute of Food Science, Food Technology, and Nutrition (ICTAN), Spanish National Research Council (CSIC), C\/Jos\u00e9 Antonio Novais 6, 28040 Madrid, Spain"},{"name":"CIBER de Diabetes y Enfermedades Metab\u00f3licas Asociadas (CIBERDEM), Instituto de Salud Carlos III (ISCIII), 28029 Madrid, Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9926-7757","authenticated-orcid":false,"given":"Jose Luis","family":"Espartero","sequence":"additional","affiliation":[{"name":"Department of Organic and Pharmaceutical Chemistry, Faculty of Pharmacy, University of Seville, 41012 Sevilla, Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2025,5,13]]},"reference":[{"key":"ref_1","unstructured":"World Health Organization (WHO) (2025, March 14). 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Int."}],"container-title":["Biomolecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/2218-273X\/15\/5\/714\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,9]],"date-time":"2025-10-09T17:31:46Z","timestamp":1760031106000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/2218-273X\/15\/5\/714"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,5,13]]},"references-count":55,"journal-issue":{"issue":"5","published-online":{"date-parts":[[2025,5]]}},"alternative-id":["biom15050714"],"URL":"https:\/\/doi.org\/10.3390\/biom15050714","relation":{},"ISSN":["2218-273X"],"issn-type":[{"value":"2218-273X","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025,5,13]]}}}