{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T02:59:36Z","timestamp":1760237976632,"version":"build-2065373602"},"reference-count":45,"publisher":"MDPI AG","issue":"7","license":[{"start":{"date-parts":[[2020,7,16]],"date-time":"2020-07-16T00:00:00Z","timestamp":1594857600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Antioxidants"],"abstract":"<jats:p>We synthesized and determined the antioxidant activity and distribution of a new cyanothiophene-based compound, N-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-3,5-dihydroxybenzamide (SIM-53B), in intact stripped olive oil-in-water emulsion. The in vitro antioxidant properties of SIM-53B were evaluated and compared to those for Trolox and resveratrol. Addition of an emulsifier (Tween 20) creates a narrow region, the aqueous\u2013oil interface, and the distribution of SIM-53B can be described by two partition constants: PWI (between aqueous\/interfacial regions) and POI (between oil\/interfacial regions). The effects of emulsifier concentration expressed in terms of the volume fraction, \u03a6I, and O\/W ratio were also evaluated on its distribution. SIM-53B is predominantly distributed (&gt;90%) in the interfacial region of 1:9 (O\/W) olive oil-in-water emulsions at the lowest emulsifier volume fraction (\u03a6I = 0.005) and only a small fraction is located in the aqueous (&lt;5%) and the oil (&lt;5%) regions. Besides, the concentration of SIM-53B in the interfacial region of the emulsions is ~170\u2013190-fold higher than the stoichiometric concentration, emphasizing the compartmentalization effects. Results suggest that the emulsifier volume fraction is a key parameter that may modulate significantly its concentration in the interface. Our study suggests that cyanothiophene-based compounds may be interesting additives for potential lipid protection in biomembranes or other lipid-based systems.<\/jats:p>","DOI":"10.3390\/antiox9070623","type":"journal-article","created":{"date-parts":[[2020,7,16]],"date-time":"2020-07-16T10:54:46Z","timestamp":1594896886000},"page":"623","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Synthesis, In Vitro Antioxidant Properties and Distribution of a New Cyanothiophene-Based Phenolic Compound in Olive Oil-In-Water Emulsions"],"prefix":"10.3390","volume":"9","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-9447-5626","authenticated-orcid":false,"given":"Sonia","family":"Losada-Barreiro","sequence":"first","affiliation":[{"name":"Physical Chemistry Department, Chemistry Faculty, University of Vigo, E-36310 Vigo, Spain"},{"name":"REQUIMTE-LAQV, Chemistry and Biochemistry Department, Science Faculty, University of Porto, PT-4169-007 Porto, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8977-3450","authenticated-orcid":false,"given":"Matej","family":"Sova","sequence":"additional","affiliation":[{"name":"Faculty of Pharmacy, University of Ljubljana, A\u0161ker\u010deva 7, 1000 Ljubljana, Slovenia"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4591-3455","authenticated-orcid":false,"given":"Janez","family":"Mravljak","sequence":"additional","affiliation":[{"name":"Faculty of Pharmacy, University of Ljubljana, A\u0161ker\u010deva 7, 1000 Ljubljana, Slovenia"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4530-8706","authenticated-orcid":false,"given":"Luciano","family":"Saso","sequence":"additional","affiliation":[{"name":"Department of Physiology and Pharmacology \u201cVittorio Erspamer\u201d, Sapienza University of Rome, 00185 Rome, Italy"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9468-0881","authenticated-orcid":false,"given":"Carlos","family":"Bravo-D\u00edaz","sequence":"additional","affiliation":[{"name":"Physical Chemistry Department, Chemistry Faculty, University of Vigo, E-36310 Vigo, Spain"}]}],"member":"1968","published-online":{"date-parts":[[2020,7,16]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"1153","DOI":"10.1021\/acsmedchemlett.8b00548","article-title":"Improving the Efficiency of the Drug Development by Expanding the Scope of the Role of Medicinal Chemists in Drug Discovery","volume":"9","author":"Webb","year":"2018","journal-title":"ACS Med. 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