Cyclodextrin Inclusion Complex Formation and Solid-State Characterization of the Natural Antioxidants α-Tocopherol and Quercetin

Cyclodextrin (CD) complexation procedures are relatively simple processes, but these techniques often require very specific conditions for each individual guest molecule. Variations of the coprecipitation from aqueous solution technique were optimized for the CD complexation of the natural antioxida...

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Bibliographic Details
Published in:Journal of agricultural and food chemistry 2009-02, Vol.57 (4), p.1162-1171
Main Authors: Koontz, John L, Marcy, Joseph E, O’Keefe, Sean F, Duncan, Susan E
Format: Article
Language:English
Subjects:
alpha-tocopherol
alpha-Tocopherol - chemistry
Analytical Methods
antioxidants
Antioxidants - chemistry
beta-Cyclodextrins - chemistry
Biological and medical sciences
Chemical Precipitation
complexation
cyclodextrin inclusion complex
cyclodextrins
Cyclodextrins - chemistry
Food industries
food preservation
food preservatives
Fundamental and applied biological sciences. Psychology
gamma-Cyclodextrins - chemistry
Magnetic Resonance Spectroscopy
quercetin
Quercetin - chemistry
Spectroscopy, Fourier Transform Infrared
Thermodynamics
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Summary:Cyclodextrin (CD) complexation procedures are relatively simple processes, but these techniques often require very specific conditions for each individual guest molecule. Variations of the coprecipitation from aqueous solution technique were optimized for the CD complexation of the natural antioxidants α-tocopherol and quercetin. Solid inclusion complex products of α-tocopherol/β-CD and quercetin/γ-CD had molar ratios of 1.7:1, which were equivalent to 18.1% (w/w) α-tocopherol and 13.0% (w/w) quercetin. The molar reactant ratios of CD/antioxidant were optimized at 8:1 to improve the yield of complexation. The product yields of α-tocopherol/β-CD and quercetin/γ-CD complexes from their individual reactants were calculated as 24 and 21% (w/w), respectively. ATR/FT-IR, 13C CP/MAS NMR, TGA, and DSC provided evidence of antioxidant interaction with CD at the molecular level, which indicated true CD inclusion complexation in the solid state. Natural antioxidant/CD inclusion complexes may serve as novel additives in controlled-release active packaging to extend the oxidative stability of foods.
ISSN:0021-8561
1520-5118
DOI:10.1021/jf802823q