The role of lipophilicity in the intensification of the sweetness of sucrose
1987
Toufieli, I.A. (American Univ. of Beirut (Lebanon). Fac. of Agriculture and Food Sc.) | Dziedzic, S.Z.
The high degree of sweetness of chlorodeoxysucrose derivatives has been attributed to the presence of AH, B, X pharmacophores in these molecules. As viewed by workers in sweeteners research, AH acts as an acid, B as a base and X as an electron-dense centre imparting a certain degree of lipophilicity to high-intensity sweeteners. The resulting AH, B, X template binds to a commensurate AH, B, X system on the taste receptor to evoke intense sweetness. The precise dimensions and location of such templates have been identified in different classes of intensely-sweet compounds. The sensory evaluation of a number of chlorinated sugars has shown that there is little evidence to support the presence of such AH, B, X pharmacophores in the sugar series. The authors believe that the overall lipophilic character, rather than the precise location of different substituents on the sugar ring determines the taste properties of sugars. Conclusions are drawn in relation to the design of "safe", highly-intense sweeteners for use in the food industry
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