Hypothesis Anionic surfactants can form stable monolayers around oil droplets via interactions with macromolecules thereby physically stabilizing high fish oil enriched emulsions (50–70% fish oil) while phenolic acids have antioxidant properties to prevent lipid oxidation. COSMO-RS (Conductor-like Screening Model for Real Solvents) is a powerful tool for the rational design of molecules with multi-functionalities. Therefore, it should be possible to assemble segments of natural molecules into a single multifunctional molecule using COSMO-RS to confer both physical and oxidative stability to fish oil enriched systems. Experiments COSMO-RS was used to predict the thermodynamic properties of series phenoleoyl malic acid esters of monoglycerides in comparison with commercial emulsifiers. A novel series of amphiphilic lipids, equipped with multi-functional groups from natural building blocks (fatty-acyl, glycerol, malic & phenolic acids), were then synthesized in a facile approach and characterized by various spectroscopy techniques. Oil-in-water emulsions stabilized by the amphiphilic lipids were formulated and characterized by dynamic light scattering measurements and fluorescence imaging. Findings An elaborate integration of multi-functions into a single molecule was achieved, displaying superior or comparable emulsion stability and antioxidant property, compared to a commercial emulsifier, phenolic acids and their combinations. This is the first report to holistically integrate the rational design, synthesis and functional characterization of natural-based multifunctional molecules for high capacity fish oil delivery systems.
Bibliographical noteFunding Information:
Technical support from the Interdisciplinary NanoScience Center (iNANO) and the Department of Engineering, Aarhus University is fully acknowledged. Peter R. Ogilby of the Department of Chemistry, Aarhus University is acknowledged for allowing access to equipment in his laboratory. The Danish council for independent research (DFF–4184-00123) is further acknowledged for financial support. B.P. also thanks the Danish Council for Independent Research for her postdoctoral grant 5054-00062B.
- Dual functionality
- Fish oil-in-water emulsions
- Interfacial activity
- Lipid oxidation
- Rational design