Di-D-fructose dianhydride-enriched products by acid ion-exchange resin-promoted caramelization of D-fructose: chemical analyses

J Agric Food Chem. 2010 Feb 10;58(3):1777-87. doi: 10.1021/jf903354y.

Abstract

Caramelization commonly occurs when sugars, or products containing a high proportion of sugars, are heated either dry or in concentrated aqueous solutions, alone or in the presence of certain additives. Upon thermal treatment of sugars, dehydration and self-condensation reactions occur, giving rise to volatiles (principally 2-hydroxymethylfurfural, HMF), pigments (melanoidines) and oligosaccharidic material, among which di-D-fructose dianhydrides (DFAs) and glycosylated DFA derivatives of different degree of polymerization (DP) have been identified. This study reports a methodology to produce caramel-like products with a high content of DFAs and oligosaccharides thereof from commercial D-fructose based on the use of acid ion-exchange resins as caramelization promotors. The rate of formation of these compounds as a function of D-fructose concentration, catalyst proportion, temperature, catalyst nature and particle size has been investigated. The use of sulfonic acid resins allows conducting caramelization at remarkable low temperatures (70-90 degrees C) to reach conversions into DFA derivatives up to 70-80% in 1-2 h, with relative proportions of HMF < 2%.The relative abundance of individual DFA structures can be modulated by acting on the catalyst nature and reaction conditions, which offers a unique opportunity for nutritional studies of DFA-enriched products with well-defined compositions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Candy
  • Carbohydrates / chemistry*
  • Disaccharides / chemistry*
  • Fructose / chemistry*
  • Ion Exchange Resins / chemistry*
  • Sulfonic Acids / chemistry

Substances

  • Carbohydrates
  • Disaccharides
  • Ion Exchange Resins
  • Sulfonic Acids
  • caramel coloring
  • Fructose