Preparation and Characterization of Octenyl Succinate β-Cyclodextrin and Vitamin E Inclusion Complex and Its Application in Emulsion

Molecules. 2020 Feb 4;25(3):654. doi: 10.3390/molecules25030654.

Abstract

Vitamin E (VE) and β-cyclodextrin (β-CD) can form an inclusion complex; however, the inclusion rate is low because of the weak interaction between VE and β-CD. The results of a molecular docking study showed that the oxygen atom in the five-membered ring of octenyl succinic anhydride (OSA) formed a strong hydrogen bond interaction (1.89 Å) with the hydrogen atom in the hydroxyl group of C-6. Therefore, β-CD was modified using OSA to produce octenyl succinic-β-cyclodextrin (OCD). The inclusion complexes were then prepared using OCD with VE. The properties of the inclusion complex were investigated by Fourier-transform infrared spectroscopy (FT-IR), 13C CP/MAS NMR, scanning electron microscopy (SEM), and atomic force microscopy (AFM). The results demonstrated that VE had been embedded into the cavity of OCD. Furthermore, the emulsifying properties (particle size distribution, ζ-potential, and creaming index) of the OCD/VE inclusion-complex-stabilized emulsion were compared with that stabilized by β-CD, OCD, and an OCD/VE physical mixture. The results showed that the introduction of the OS group and VE could improve the physical stability of the emulsion. In addition, the OCD/VE inclusion complex showed the strongest ability to protect the oil in the emulsion from oxidation. OCD/VE inclusion complex was able to improve the physical and oxidative stability of the emulsion, which is of great significance to the food industry.

Keywords: emulsifying property; inclusion complex; octenyl succinic β-cyclodextrin; oxidation stability; vitamin E.

MeSH terms

  • Antioxidants / chemistry
  • Emulsions / chemistry*
  • Food Industry / methods
  • Food Preservation / methods*
  • Lipid Peroxidation / drug effects
  • Microscopy, Atomic Force
  • Molecular Docking Simulation
  • Nuclear Magnetic Resonance, Biomolecular
  • Spectroscopy, Fourier Transform Infrared
  • Succinates / chemistry*
  • Vitamin E / chemistry*
  • beta-Cyclodextrins / chemistry*

Substances

  • Antioxidants
  • Emulsions
  • Succinates
  • beta-Cyclodextrins
  • Vitamin E
  • octenyl succinate