Sweeteners, potency

Fig. 3. Structure—activity summary of dipeptide sweeteners, where n may be 0 or 1 (62). There are no known replacements for the acid or amide groups denoted by arrows, although thioamide has some sweetness. If the NH2 is replaced by NHC(0)R, the potency is increased when...

The disaccharide stmcture of (12) (trade name SPLENDA) is emphasized by the manufacturer as responsible for a taste quaUty and time—intensity profile closer to that of sucrose than any other high potency sweetener. The sweetness potency at the 10% sucrose solution sweetness equivalence is between 450 and 500X, or about two and one-half times that of aspartame. When compared to a 2% sugar solution, the potency of sucralose can be as high as 750X. A moderate degree of synergy between sucralose and other nonnutritive (91) or nutritive (92) sweeteners has been reported. 

Alitame (trade name Adame) is a water-soluble, crystalline powder of high sweetness potency (2000X, 10% sucrose solution sweetness equivalence). The sweet taste is clean, and the time—intensity profile is similar to that of aspartame. Because it is a stericaHy hindered amide rather than an ester, ahtame is expected to be more stable than aspartame. At pH 2 to 4, the half-life of aUtame in solution is reported to be twice that of aspartame. The main decomposition pathways (Fig. 6) include conversion to the unsweet P-aspartic isomer (17) and hydrolysis to aspartic acid and alanine amide (96). No cyclization to diketopiperazine or hydrolysis of the alanine amide bond has been reported. AUtame-sweetened beverages, particularly colas, that have a pH below 4.0 can develop an off-flavor which can be avoided or minimized by the addition of edetic acid (EDTA) [60-00-4] (97). 

Thaumatin (trade name Talin) is a very potent sweetener (ca 2000X, 10% sucrose solution sweetness equivalence). However, its potency is overshadowed by inferior taste quaUties. The onset of sweetness is very slow, and after reaching the maximum sweetness, a very long-lingering sweetness combined with an unpleasant aftertaste follows. Primarily owing to this poor taste quaUty, thaumatin is not considered a practically useflil sweetener. It is, however, used as a flavor enhancer, especially in products such as chewing gum. Thaumatin and thaumatin B-recombinant were affirmed GRAS flavors (EEMA no. 3732 and 3814, respectively). They are not approved as sweeteners in the United States. 

Finally, some amphiphilic sweeteners, eg, aspartame, saccharin, and neohesperidin dihydrochalcone, have been shown to be capable of stimulating a purified G-protein direcdy in an in vitro assay (136). This suggests some sweeteners may be able to cross the plasma membrane and stimulate the G-protein without first binding to a receptor. This type of action could explain the relatively longer response times and the lingering of taste associated with many high potency sweeteners. 

The metabolic and pharmacokinetic profile of sucralose (this is a novel intense sweetener with a potency about 600 times that of sucrose) in human volunteers was studied by Roberts and coworkers [82]. Part of this study was realized using PLC in the following chromatographic system in which the stationary phase was silica gel and the mobile phase was ethyl acetate-methanol-water-concentrated ammonia (60 20 10 2, v/v). Separated substances were scraped off separately, suspended in methanol, and analyzed by filtration, scintillation counting, or enzymatic assay. It was shown that the characteristics of sucralose include poor absorption, rapid elimination, limited conjugative metabolism of the fraction absorbed, and lack of bio-accumulative potential. 

Abstract Aspartame (Apt), Acesulfame-K (Ace-K) low-calorie, high-potency artificial sweeteners ate cnnently nsed in beverages and dietary food and drinks. Their increased application in food and drink prodncts has given a new impetus to develop fast and accurate methods for their determination. Absorption spectra of Asp, Caf, Ace-K and BA strongly overlap. Therefore a direct determination of these analytes in quaternary mixture is impossible without a separation step. In order to overcome this difficulty partial least squares (PLS) method has been proposed. 

Alitame is high potency sweetener, although it is more stable than aspartame, the control of sweetness of food is difficult while using it. 

Kinghorn AD, Compadte CM, Less common high potency sweetenets, in O Brien Nabors L (ed.). Alternative Sweeteners, 3rd ed.. Revised and Expanded, Marcel Dekker, New York, pp. 204—231, 2001. 

The worldwide demand for high potency sweeteners is increasing and, with blending of different sweeteners becoming a standard practice, the demand for the search of alternative natural sweeteners is also increasing. Due to many adverse effects of artificial sweeteners such as, for example, aspartame, sucralose, acesulphame K and the natural sweetener sucrose... 

These workers proceeded to carry out theoretical conformational analyses of a set of sweeteners, many of which have multiple A-H and/or B sites. The set of compounds analyzed are reported in Table I along with the sweet potency relative to sucrose. A fixed valence geometry molecular mechanics force field was used in the conformational analyses. The conformational search strategy was as follows ... 

Aspartame. Aspartame [22839-47-0] [53906-69-1] (APM, L-aspartyl-L-phenylalanine methyl ester) (1), also known under the trade names of NutraSweet and EQUAL, is the most widely used nonnutritive sweetener worldwide. This dipeptide ester was synthesized as an intermediate for an antiulcer peptide at G. D. Searle in 1965. Although this compound was known in the literature, its sweet taste was serendipitously discovered when a chemist licked his finger which was contaminated with it. Many analogues, especially the more stable esters, were made (6) and their taste qualities and potencies determined. It was the first compound to be chosen for commercial development. Following the purchase of G. D. Searle by Monsanto, the aspartame business was split off to become a separate Monsanto subsidiary called the NutraSweet Company. 

L-Aspartic acid (12) is an industrially important, large volume, chiral compound. The primary use of aspartic acid in the fine chemical arena is in the production of aspartame, a high potency sweetener (Chapter 31). Other uses of L-aspartate include dietary supplements, pharmaceuticals, production of alanine (by decarboxylation), antibacterial agents, and lubricating compounds. There have been a number of reviews on L-aspartate production.53 56... 

Sucralose (2), 4,l, 6 -trichloro-4,l, 6 -trideoxy-ga/actosucrose (TGS), is a trichloro disaccharide nonnutritive sweetener.18 This compound was discovered through a systematic study in which sucrose derivatives were prepared. It was found that substitution of certain hydroxy groups by a halogen increased the sweetness potency dramatically.19 20 Sucralose was chosen as the development candidate by Tate and Lyle.21-24... 

A. D. Kinghorn C. M. Compadre, Less Common High-Potency Sweeteners. In Alternative Sweeteners, 3rd ed. Revised and Expanded L. 0. Nabors, Ed., Marcel Dekker, Inc. New York, 2001 pp 209-233. 

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