Synthesis, In Vitro Antioxidant Properties and Distribution of a New Cyanothiophene-Based Phenolic Compound in Olive Oil-In-Water Emulsions

• Main Authors: Sonia Losada-Barreiro (Author), Matej Sova (Author), Janez Mravljak (Author), Luciano Saso (Author), Carlos Bravo-Díaz (Author)
• Format: Book
• Published: MDPI AG, 2020-07-01T00:00:00Z.
• Subjects: article
• Online Access: Connect to this object online.

Summary

We synthesized and determined the antioxidant activity and distribution of a new cyanothiophene-based compound, <i>N</i>-(3-cyano-4,5,6,7-tetrahydrobenzo[<i>b</i>]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-oil interface, and the distribution of SIM-53B can be described by two partition constants: <i>P</i>_W^I (between aqueous/interfacial regions) and <i>P</i>_O^I (between oil/interfacial regions). The effects of emulsifier concentration expressed in terms of the volume fraction, Φ_I, and O/W ratio were also evaluated on its distribution. SIM-53B is predominantly distributed (>90%) in the interfacial region of 1:9 (O/W) olive oil-in-water emulsions at the lowest emulsifier volume fraction (Φ_I = 0.005) and only a small fraction is located in the aqueous (<5%) and the oil (<5%) regions. Besides, the concentration of SIM-53B in the interfacial region of the emulsions is ~170-190-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.

Item Description

10.3390/antiox9070623
2076-3921