Difructose dianhydrides

Thermal activation of sucrose and inulin in the presence of citric acid,93 and sucrose in the presence of acetic94 acid, yields caramels containing, among other products, di-D-fructose dianhydrides and glycosylated difructose dianhydrides, as described in Section V.6). Similarly, the thermal treatment of 6-0-ot-D-glu-copyranosyl-D-fructofuranose (palatinose) in the presence of citric acid87 has been shown to produce appreciable proportions of glucosylated di-D-fructose dianhydrides. 

Manley-Harris, M. and Richards, G.N., Di-D-difructose dianhydrides and related oligomers from thermal treatments of innhn and sucrose. Carbohydrate Res., 287, 183, 1997. 

Christian, T.J. et al.. Kinetics of formation of di-D-difructose dianhydrides dining thermal treatments of inulin, J. Agric. Food Chem., 48, 1823, 2000. 

Diheterolevulosans (difructose dianhydrides) are obtained by refluxing concentrated aqueous solutions of D-fructose.96 97 Chromatography of Cuban blackstrap molasses in a pilot-plant-scale chromatogram on fuller s earth clay did not reveal the presence of these substances.98... 

Depending on the process (acid- or base-catalyzed, leading to aromatic or color caramel) and on the particular sugar substrate (sucrose, fructose), different proportions and types of these molecules can be found.291 Some of the caramel components are similar to those observed when fructose and sucrose react in hydrogen fluoride, notably bisglycosylated difructose dianhydrides.287 341... 

J. M. Garcia Fernandez, A. Gadelle, and J. Defaye, Difructose dianhydrides from sucrose and fructooligosaccharides and their use as building blocks for the preparation of amphiphiles, liquid crystals and polymers, Carbohydr. Res., 265 (1994) 249-269. 

J. Defaye and J. M. G. Fernandez, Difructose dianhydrides as synthetic intermediates, Synthesis of 3,6-anhydro-keto-D-fructose, Tetrahedron Asymmetry, 5 (1994) 2241-2250. 

Ingestion of difructose dianhydride III improves the population and properties of the microorganisms in the intestines, but apparently differently from other oligosaccharides (Saito and Tomita, 2000). Likewise, it improves calcium absorption in the small intestine via a mechanism that appears to differ from other known stimulants. 

Engels, D., Alireza, H.B., Kunz, M., Mattes, R., Munir, M., and Vogel, M., Modified Streptococcus Gene ftf and Fructosyltransferase and Their Use in Preparation of Inulin, Fructooligosaccharides, and Difructose Dianhydride for Use in Food and Feed, WO Patent 2002050257, 2002. 

Kobayashi, S., Seki, K., Kishimoto, M., Kadoma, M., Takano, T., Nagata, K., and Onbo, K., Manufacture of Difructose Dianhydride from Inulin with Immobilized Inulin Fructotransferase, Japanese Patent 01285195, 1989. 

A method is described for the production of difructose-dianhydride I (DFAI) in high yield, by reacting an inulin-containing solution (e.g., from Jerusalem artichoke) with an in-ulinase derived from a bacterium of the genus Streptomyces. 

Difructose Dianhydrides (DFAs) and DFA-Enriched Products as Functional Foods... 

Keywords Caramel, Difructose dianhydrides, Fructose, Functional foods, Inulin, Prebiotics, Sucrose... 

Publications on DFAs have frequently suffered from confusion regarding wrmig stmctural assignment of some diastereomers until recent times. In addition, the old notation system based on the use of the terms difructose dianhydride (DFA ... 

Another example of the crystallization of chemically related compounds is found in the commercial separation of fructose from the impurity difructose dianhydride (Chu et al. 1989). Fructose undergoes irreversible dehydration during the crystallization process to yield several forms of difructose dianhydride impurities. Since the difructose dianhydride molecule consists of two fructose moieties, it exhibits some of the chemical and structural features of the host fructose molecule. In an analogous fashion to a tailor-made additive, the difructose dianhydride impurities appear to incorporate into the crystal (at < 1 wt% level), thus inhibiting the subsequent adsorption and growth of fructose molecules. The resulting fructose crystal growth rates are so low that the crystallization time in fructose manufacture is often on the order of days. 

The anhydrodisaccharides a-D-fructofuranose-P-D-fructopyranose 1,2 2,1 -dianhydride and a-D-fructofiiranose-P-D-fructofiiranose l,2 2,r-dianhydride have been identified in the ethanol-soluble products from the thermolysis of sucrose. These same products, along with di-P-D-fructofuranose-l,2 2,r-dianhydride, were found in caramelized sucrose. Dissolution of sucrose in anhydrous HF afforded a complex mixture of difructose dianhydrides and their glucosylated derivatives as well as oligosaccharides up to dp 14. a-D-Fructofuranose-P-D-fiructopyranose l,2 2,r-dianhydride was the main component in the mixture, either free or glucosylated at various positions. The reaction of some disacdiarides with anhydrous HF has afibrded some dimeric dianhydrides. Palatinose, leucrose and maltulose gave, respectively, the dianhydrides 25, 26 and 27. a-D-Fructofuranose-P-D-fmctofuranose-l,2 2,r-dianhydride has been converted into the bis-3,6-anhydro-derivative, which,... 

The chemisry of the hexulosyl bromide 20 has beat studied and a facile synthesis of the azidogalactosyl bromide 21 by way of D-galactal triacetate has been outlined. The conversion of 6-bromo-6-deoxyaldonolactones into 3,6-anhydro-aldonic acids is covered in Chapter 16 and the conversion of difructose dianhydride by way of deoxyhalo derivatives into 3,6-anhydro-keto-D-fructose is mentioned... 

In the first effect water is present at a significantly higher concentration than the solutes viz., sucrose, invert and PPCC), and therefore, the reaction of Fru with water to produce D-fructose predominates. In fact, in dilute solution, prior to evaporation, the above mentioned alternative reactions are unlikely. In later effects, as the concentration of solutes increases, the alternative reactions become more likely, i.e., small amounts of kestoses and difructose dianhydrides may form in the later stages of evaporation if there is any further sucrose hydrolysis. 

Difructose dianhydrides (DFDA) are one class of compounds that are present in 3rdS but absent in MJ. These DFDAs which probably form late in the evaporation process (when water concentration is lowest, see section 2.1) coelute with sucrose under most capillary GC conditions. Formation of DFDAs may significantly reduce the sucrose loss estimated by GC-FID (Glc%Suc) in the 3rd effect. 

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