Sucrose substitutes saccharin

Saccharin is approximately 300 times as sweet as sucrose but can have a bitter after-taste in concentrated solution it is non-calorific, does not contribute to the problem of obesity or tooth decay, and can be used by diabetics as a sugar substitute. Saccharin is stable to heat and so can be used in cooking. A number of saccharin derivatives, e.g. (88a)-(88e), have been synthesised as potential sweetening agents (Figure 12). 

The binding specificity of d-[ C]glucose by the taste-papillae membranes, compared to that of control membranes isolated from epithelial tissue, has been confirmed in two studies. One inherent problem in the approach is that the stimuli, primarily carbohydrate sweeteners, are not ideal model compounds to use, as they are not active at low concentrations and do not show sufficiently high binding-constants. The use of other stimulus compounds that are at least several hundred times sweeter than sucrose, such as saccharin, dihydrochalcone sweeteners, dipeptide sweeteners, stevioside, perillartine and other sweet oximes, the 2-substituted 5-nitroanilines, and... 

Based on dilution in distilled water to threshold sweetness 1 is about 300 times as sweet as sucrose.30 Results with about 80 saccharin derivatives indicate that substitution in the 2- or 3-position gives tasteless compounds.82 Exceptions are Mannich bases (20) and 3-oxo-2-hydroxy-methyl-2,3-dihydrobenz[d]isothiazole-l,1-dioxide (21) which possess a... 

Because it has no caloric value, when it became commercially available in 1885, saccharin became an important substitute for sucrose. The chief nutritional problem in the West was—and still is—the overconsumption of sugar and its consequences obesity, heart disease, and dental decay. Saccharin is also important to diabetics, who must limit their consumption of sucrose and glucose. Although the toxicity of saccharin was not studied carefully when the compound first became available to the public (our current concern with toxicity is a fairly recent development), extensive studies done since... 

Substitution of one or more of the -OH groups of sucrose by a -Cl atom has a profound effect on its taste thus it may greatly increase the intensity of its sweetness or abolish it altogether. The most promising of these chlorinated sugars as an alternative sweetener is Sucralose which has a Cl atom substituted on carbon atoms 4,1 and 6. It is 650 times sweeter than sucrose itself, lacks the unpleasant aftertaste of saccharin and gives no evidence of any adverse effects. It will be interesting to see if it becomes a commercial success. 

There are a number of sugar substitutes, or artificial sweeteners on the market the most popular are saccharin, aspartame, sucralose, and cyclamate. Many of these were discovered by accident, when a chemist did something you re never supposed to do in a chemistry lab - lick your fingers. In the case of sodium cyclamate, the graduate student had put his cigarette on the side of the lab bench (yes, you were allowed to smoke in chemistry labs in 1937 ), and when he put it back in his mouth it tasted sweet. The advantage of these artificial sweeteners comes from the fact that they are often many times as sweet as sucrose, which means you don t need to use very much of them, and also that they are not metabolized in the same way as sugar, so you don t get fat. They also don t cause tooth decay. 

The chlorosulfonation of toluene by treatment with excess chlorosulfonic acid yields a mixture of the ortho and para sulfonyl chlorides, but the mixture may be separated by freezing out the solid p-isomer (see Chapter 4, p 37). Saccharin 25 contains an acidic hydrogen atom and is generally formulated as the sodium salt to increase water solubility. It is some 300 times sweeter than sucrose and is non-calorific so can be used by diabetics as a sugar substitute. A number of saccharin derivatives have been synthesized as potential sweetening agents (Chapter 6, ref. 33). 

The relatively low degrees of sweetness of carbohydrates when compared with the sweetness of some noncarbohydrate compounds such as cyclamates, saccharin, certain aminoacids, and so on (see Fig. 5.3) can be explained by the relatively weak hydrophobic character of the C-6 hydroxymethyl group found in many pyranoses. However, the presence of a hydrophobic sweetness intensifier can explain why certain carbohydrates are much sweeter than other carbohydrates for example, D-fructose and D-xylose are much sweeter than D-glucose and sucrose (see Table 5.1). Both D-fructopyranose and D-xylopyranose (the predominant forms of D-fructose and D-xylose in solution and in the crystalline state) have methylene groups that are not substituted by a hydroxyl group, and hence are more hydrophobic and produce a sweeter taste (see Fig. 5.5). 

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