Author(s): Roque, Catarina ; Castro, Mariana ; Castro, Tarsila Gabriel ; Ribeiro, Artur ; Silva, C. ; Cavaco-Paulo, Artur ; Noro, Jennifer Martins
Date: 2025
Persistent ID: https://hdl.handle.net/1822/94709
Origin: RepositóriUM - Universidade do Minho
Subject(s): Amphiphilic esters; Biosynthesis; Encapsulation; Molecular dynamics simulations; Nanoemulsions
In this work, several amphiphilic compounds were successfully synthesized via lipase-catalysis: 2-(2-ethoxyethoxy)ethyloctanoate, 2-(2-ethoxyethoxy)ethyldecanoate, 2-(2-ethoxyethoxy)ethylpalmitate, (2-(2-ethoxyethoxy)ethyloleate) and (2-(2-ethoxyethoxy)ethyllinoleate). The reactions were carried out using octanoic acid, decanoic acid, palmitic acid, oleic acid, and linoleic acid, as the aliphatic compounds, and 2-(2-ethoxyethoxy)ethanol, as the hydrophilic source. The ester products were subjected to an in-depth characterization to evaluate their potential as emulsifiers. The data revealed that esters composed of decanoate, oleate, and linoleate chains successfully formed stable emulsions, maintaining stability for up to 18 months. Encapsulation of the hydrophobic dye, Nile red, demonstrated that the resulting nanoemulsions are promising vehicles for the long-term storage of lipophilic molecules. Complementary molecular dynamics simulations were performed to evaluate the spontaneous assembly of esters into nanoemulsions, which agreed with the experimental findings. The remarkable stability of these nanoemulsions makes them suitable for numerous applications, such as food, cosmetics, and pharmaceuticals.
