Sweeteners, artificial sodium cyclamate

Examine the structures oisucrose, the natural sweetener, and saccharin, sodium cyclamate and aspartame (Nutrasweet), three of the most common artificial sweeteners. What, if any, structural features do these molecules have in common Compare electrostatic potential maps for the different sweeteners. Are there any significant features in common Based on yom findings, do you think it is likely that entirely different artifical sweeteners might be discovered Explain. 

Cyclohexylamine is a metabolite of the artificial sweetener sodium cyclamate, with the amount of conversion varying considerably from person to person. ... 

A first requirement for a substance to produce a taste is that it be water soluble. The relationship between the chemical structure of a compound and its taste is more easily established than that between structure and smell. In general, all acid substances are sour. Sodium chloride and other salts are salty, but as constituent atoms get bigger, a bitter taste develops. Potassium bromide is both salty and bitter, and potassium iodide is predominantly bitter. Sweetness is a property of sugars and related compounds but also of lead acetate, beryllium salts, and many other substances such as the artificial sweeteners saccharin and cyclamate. Bitterness is exhibited by alkaloids such as quinine, picric acid, and heavy metal salts. 

Schmahl D, Habs M. Investigations on the carcinogenicity of the artificial sweeteners sodium cyclamate and sodium saccharin in rats in a two-generation experiment. Arzneimittelforschung 1984 34 604-606. 

The artificial sweeteners, saccharin and cyclamate, and their sodium and calcium salts, may be used in low-calorie foods and saccharin is permitted in certain low-calorie soft drinks. If manufacturers wish to use an additive which is not listed as permitted and is not specifically prohibited, they may obtain permission from the Minister of Health. 

Sodium cyclamate (SO-dee-um SYE-kla-mate) is a white, crystal solid or powder with almost no odor and a very sweet taste. Its sweetening power is about 30 times that of table sugar, the standard against which artificial sweeteners are measured. Because of its sweet flavor, sodium cyclamate is used as an artificial sweetener. 

Sodium cyclamate and calcium cyclamate are used as artificial sweeteners. Since they have no nutritional value... 

Sodium cyclamate, an artificial sweetener found in diet foods, drinks and some pharmaceuticals, can also markedly reduce the absorption of lincomycin. The AUC of lincomycin 500 mg was reduced by about 75% by 1 Molar equivalent of sodium cyciamate (said to be an amount equal to only part of a bottle of diet drink, but exact quantity not stated). ... 

Artificial sweeteners Saccharin sodium (0.01-0.5 % mostly 0.1 %), aspartame, acesulfame potassium and sodium cyclamate... 

Another artificial sweetener, which gained wide use in the 1960s and 1970s, is sodium cyclamate. Sodium cyclamate, which is 33 times as sweet as sucrose, belongs to the class of compounds known as the sulfamates. The sweet taste of many of the sulfamates has been known since 1937, when Sveda accidentally discovered that sodium cyclamate had a powerfully sweet taste. The availability of sodium cyclamate spurred the popularity of diet soft drinks. Unfortunately, in the 1970s, research showed that a metabolite of sodium cyclamate, cyclohexylamine, posed some potentially serious health risks, including a risk of cancer. This sweetener has thus been withdrawn from the market. 

On the other hand, several cinchona alkaloid-derived primary amines have been successfully investigated as organocatalysts for asymmetric Michael additions of ketones to Michael acceptors. As an example, Lu et al. have described the first Michael addition of cyclic ketones to vinyl sulfone catalysed by a catalyst of this type, providing an easy access to chiral a-alkylated carbonyl compounds with high yields and enantioselectivities of up to 96% ee, albeit with moderate diastereoselectivities (<72% de), as shown in Scheme 1.21. This novel methodology was apphed to the synthesis of sodium cyclamate, an important compound in the artificial sweeteners industry. 

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. 

With primary or secondary amines, chlorosulfonic acid yields the corresponding sulfamic acid (Equation 5) this reaction with cyclohexylamine afforded the artificial sweetener sodium cyclamate 3 (Equation 9). In contrast to alkanes, alkenes readily react with chlorosulfonic acid to give the alkyl chlorosulfonates thus ethylene (ethene) is absorbed by chlorosulfonic acid to give ethyl chlorosul-fonate 4 (Equation 10). 

A non-aqueous differentiating titration procedure (39) involves passage of the artificial sweeteners mixture through a cationic exchange resin, Dowex 50-X8, to separate and convert saccharin to its acid form. The solution obtained is titrated potentiometrically in methyl isobutyl ketone with 0.1 N sodium methoxide. The method has been applied in presence of cyclamate and benzyl alcohol. 

Saccharin or its sodium and calcium salts are used as sweeteners. Aspartame is also employed as a sweetener in effervescent tablets. Earlier, cyclamates and cyclamic acid were the artificial sweeteners of choice, but their use has now been restricted. 

The artificial sweeteners saccharin (2,3-d1hydro-3-oxybenz1so-sulphonazole) and the sodium and calcium salts of cyclamate (N-cy-clohexylsulphamate) are effective promoters of tumors In the rat urinary bladder (Hicks et., 1973 Hicks al., 1975). Animals Initiated with N-methyl-N-mtrosourea (NMU) at 3oses that did not... 

RPLC with MS detection was used for the analysis of seven artificial sweeteners (aspartame, saccharin, acesulfame-K, neotame, sucralose, cyclamate, and alitame) and one natural sweetener (stevioside). Samples were extracted using methanokwater and injected without any cleanup into the LC—MS system. Separation is carried out using a Cis column and gradient elution. Sweeteners were quantified using selective-ionization recording (SIR) at m/z 178, 397, 377, 293, 641, 312, 162, and 182 for cyclamate, sucralose, neotame, aspartame, stevioside, alitame, acesulfame-K, and saccharin, respectively, with a warfarin sodium m/z = 307) used as an internal standard [24]. For a detailed discussion of other analytical methods to determine artificial sweeteners, refer to [25]. 

Sodium iV-cyclohexyl sulfamate (cycliunate, 141 R = cyclohexyl) was introduced as a non-nutritive artificial sweetener in 1939. It is 30 times sweeter than sucrose, but was banned in the USA and Canada in 1970 because rats fed with large doses developed bladder cancer, although it is permitted in many other countries. Cyclohexylammonium sulfamate, an intermediate in the manufacture of non-nutritive sweeteners, may be prepared by reaction of cyclohexylamine (two to three equivalents) with chlorosulfonic acid in trichloroethene at 60-75 C the presence of the excess amine avoids an acidic medium and side reactions. A-Cyclohexylsulfamic acid has been obtained by treatment of cyclohexylamine with a mixture of sulfur trioxide and chlorosulfonic acid in trichloroethene at < 60 Cyclamate can also be manufactured by heating cyclohexylamine with sulfamic acid in xylene at 132-139 Benson and Spillane discussed the... 

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