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.
Highlights
Lipid oxidation is one of the major deteriorative chemical changes that can decrease the quality and safety of products such as milk, cream, coffee whiteners, cream liqueurs, mayonnaise, salad dressings, cheese, spreads, yoghurts, and infant formula, especially in their emulsified forms [1,2,3]
The six-membered epoxy ring in the Vitamin E (VE) molecule was located in the cavity of β-CD, the benzene ring was at the large end of β-CD, and the hydrophobic carbon chain was at the small end of β-CD
The droplet size of the β-CD-stabilized emulsion was significantly higher than that of those stabilized by octenyl succinic-β-cyclodextrin (OCD), which was due to the introduction of octen-1-ylsuccinic anhydride (OSA) groups enhancing the surface activity of β-CD
Summary
Lipid oxidation is one of the major deteriorative chemical changes that can decrease the quality and safety of products such as milk, cream, coffee whiteners, cream liqueurs, mayonnaise, salad dressings, cheese, spreads, yoghurts, and infant formula, especially in their emulsified forms [1,2,3]. Because of the larger contact surface area between oil droplets and oxidants (oxygen, free radicals, and chelating metals), the lipid in the emulsion is much more susceptible to oxidative deterioration than bulk oil [4]. A sufficient amount of the antioxidant is needed at the oil–water interface to prevent oxidative species (oxygen, free radicals, transition metals, and lipolytic enzymes) contacting the oil. Surface-active emulsifiers can adsorb to the oil–water interface, forming a protective membrane which, its thickness is only a few nanometers, plays important roles in enhancing the physical stability of emulsion droplets and delaying lipid oxidation processes by acting as a barrier to the penetration and diffusion of oxidizing agents [6]. Transition metals, especially iron, are basic components in food systems, and they can catalyze the oxidation of dispersed lipids at the oil–water interface [7,8]
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