Lipase-catalyzed synthesis of erythorbyl oleate and its characterization as a multifunctional emulsifier

Erythorbyl oleate (EO), a novel emulsifier with multifunctional properties, was synthesized via lipase-catalyzed solvent-free esterification between erythorbic acid and oleic acid. The reaction produced EO of 30.75 ± 1.65 mM at 60 h, monitored by high-performance liquid chromatography (HPLC) analysis. Purified EO was chemically identified as 6-O-oleoyl-erythorbic acid by HPLC-electrospray ionization/mass spectrometry (ESI-MS), ¹H nuclear magnetic resonance (NMR), and ¹³C NMR analyses, and further investigations on its multifunctionalities were conducted. EO displayed antioxidant activity equivalent to erythorbic acid in 2,2-diphenyl-1-picrylhydrazyl and 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) radical scavenging activities. Investigation of the antibacterial activity of EO against foodborne pathogens showed MICs of 0.27 ± 0.09 and 0.40 mM for Bacillus cereus ATCC 10876 and Staphylococcus aureus ATCC 12692, respectively. EO also displayed interfacial properties, lowering interfacial tension between medium-chain triglyceride oil and water to 3.40 ± 0.04 mN/m with a critical micelle concentration of 2.54 ± 0.03 mM. Dynamic light scattering analyses of the emulsion stabilized by EO demonstrated a similar polydispersity index (0.15 ± 0.00) to Tween 80-stabilized emulsion (0.28 ± 0.01), with an average droplet size of 173.2 ± 1.8 nm. In addition, the EO-stabilized emulsion exhibited a negative surface charge (-56.83 ± 4.30 mV) in zeta potential measurements, indicating sufficient electrostatic repulsion between droplets. These results suggest that EO is a multifunctional emulsifier to simultaneously control oxidative rancidification and bacterial spoilage in emulsion-based foods. Practical Application: EO was synthesized via an enzymatic esterification reaction between erythorbic acid and oleic acid. The synthetic process excluded any use of organic solvent, diminishing potential health hazards or environmental pollution associated with chemical reactions. The interfacial properties of the resultant EO, along with excellent antioxidant and antibacterial activities, propose its potential application in emulsion-based foods. Simultaneous control of bacterial spoilage and oxidative rancidification by EO would fulfill the industrial needs for extending shelf life and enhancing consumer safety.