D-fructose Dianhydrides and Industry

Uses of Di-d-fructose Dianhydrides 1. Di-D-fructose Dianhydrides and Nutrition 

In 1993, the di-D-fructose dianhydrides were summarized as being of little, if any, commercial importance. 73 However, a search of the literature reveals an appreciable number of patents issued since 1989 for the manufacture of these compounds. These include enzymic methods for the production of individual dianhydrides (Ref. 130) or methods of production of mixtures using anhydrous HF or pyridinium poly(hydrogen fluoride) (see Ref. 131). Most cite the di-D-fructose dianhydrides as low-calorie sweetening agents (Ref. 132), and some claim anti-cariogenic properties (Refs. 132 and 133). 

Di-D-fructose dianhydrides have been claimed to promote the growth of bifidobacteria in vitro.134 Bifidobacterium spp. are found in the large intestines of most vertebrates.135 The benefits attributed to the presence of a healthy population of bifidobacteria in the gut include inhibition of carcinogenesis,136 suppression of putrefactive substances,137 lowering of blood pressure and blood 

The raw materials from which di-D-fructose dianhydrides can be obtained in appreciable yield are readily available from comparatively inexpensive agricultural feedstocks. Thus, these compounds are attractive as chiral-starting materials for chemical synthesis. Their stability to acid and heat, and their relative rigidity, because of the conformational constraints covered here, are also features that might be exploited during syntheses.119 A series of variously substituted di-D-fructose dianhydrides has been prepared,119 starting from 6,6 -dideoxy-6,6 -di-halosucroses. The properties of these and other derivatives of di-D-fructose dianhydrides are summarized in Tables XIV-XX. Two of these derivatives, 48 and 56, exhibit thermotropic liquid-crystal properties.119 

The authors thank Dr. Jacques Defaye of CNRS and CEA, Departement de Recherche Fondamen-tale sur la Matiere Condensee/SESAM, Centre d Etudes de Grenoble for his helpful comments. Financial support was provided by The Sugar Association, Inc. 

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