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FT-IR and DSC results revealed that the physical state and lateral packing of synthetic molecules were largely governed by fatty acyls. The critical micelle concentrations (CMC) of synthetic lipids was in the range of 0.1\u2009mM to 2.5\u2009mM, affording generation of stable oil-in-water emulsions; as evidenced by the creaming index (&lt;5%) of emulsions stabilized by compounds <jats:bold>C12<\/jats:bold>\u2012<jats:bold>C16<\/jats:bold>, and <jats:bold>C12a<\/jats:bold>\u2012<jats:bold>C16a<\/jats:bold> after 7 days\u2019 storage. AFM analysis revealed that compound <jats:bold>C14<\/jats:bold> formed stable double-layers films of 5.2\u2009nm and 6.7\u2009nm. Application studies showed that formulations stabilized by synthesized compounds containing 30% fish oil had superior physical and oxidative stability compared to formulations containing commercial emulsifiers or their mixtures with phenolic acids. Moreover, the synthetic compounds were non-toxic against <jats:italic>in vitro<\/jats:italic> transformed keratinocytes from histologically normal skin and Caco-2 cell lines. This study demonstrates the relevance of using a natural hydroxycarboxylic acid as a flexible linker between natural antioxidants, glycerol and fatty acids to generate multifunctional amphiphiles with potential applications in food, pharmaceutical and cosmetic industry.<\/jats:p>","DOI":"10.1038\/s41598-018-19336-8","type":"journal-article","created":{"date-parts":[[2018,1,10]],"date-time":"2018-01-10T11:41:52Z","timestamp":1515584512000},"update-policy":"https:\/\/doi.org\/10.1007\/springer_crossmark_policy","source":"Crossref","is-referenced-by-count":10,"title":["A new group of synthetic phenolic-containing amphiphilic molecules for multipurpose applications: Physico-chemical characterization and cell-toxicity study"],"prefix":"10.1038","volume":"8","author":[{"given":"Sampson","family":"Anankanbil","sequence":"first","affiliation":[]},{"given":"Bianca","family":"P\u00e9rez","sequence":"additional","affiliation":[]},{"given":"Iva","family":"Fernandes","sequence":"additional","affiliation":[]},{"given":"Katarzyna Magdalena","family":"Widzisz","sequence":"additional","affiliation":[]},{"given":"Zegao","family":"Wang","sequence":"additional","affiliation":[]},{"given":"Nuno","family":"Mateus","sequence":"additional","affiliation":[]},{"given":"Zheng","family":"Guo","sequence":"additional","affiliation":[]}],"member":"297","published-online":{"date-parts":[[2018,1,16]]},"reference":[{"key":"19336_CR1","doi-asserted-by":"publisher","first-page":"664","DOI":"10.1016\/j.foodchem.2016.11.121","volume":"221","author":"M Balakrishna","year":"2017","unstructured":"Balakrishna, M. et al. 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