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A breakthrough in the design of novel sugar MNSs was described by DuBois et al. in 1992 (110). They identified a wide variety of cleanly sweet sugar MNSs. This work focused on the design of replacements for sucrose and, therefore, to reproduce the colligative properties of sucrose (freezing point depression, etc), novel molecules with molecular weight comparable to that of sucrose were designed. In addition, this work was based on recognition of the fact that neutral, polyhydroxylic organic compounds of low molecular weight, in general, are sweet. Thus, in the attempt to reproduce the taste of sucrose, novel molecules with the same ratio of C atoms to OH groups as exhibited by sucrose (ie, C/OH = 1.5) were identified as targets for synthesis and evaluation. One of the preferred sugar MNS sweeteners identified in this work is polyol 25. This sweetener exhibits a clean sweet taste and a Pw of 0.46 which is independent of sucrose reference concentration. This polyol is very stable and quite water soluble. Sugar MNS 25 is easily prepared in quantitative yield in one step on reaction of gluconolactone with 1-amino-l-deoxy-sorbitol. The latter starting material is commercially available and is easily prepared by reductive amination of glucose with ammonia. Of particular interest is the fact that 25 is not fermented at all by human fecal bacteria and therefore has an apparent bioavailable calorie content of 0 Cal/g.

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