Sweet alitame

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). 

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

In the future aspartame can expect to encounter competition from new high intensity sweeteners such as sucralose which is produced by Tate Lyle/Johnson Johnson and alitame (Pfizer), which have advantages such as even higher sweetness and, in the case of sucralose, heat stability. In response Nutrasweet are busy developing a new very high intensity sweetener (Sweetener 2000), which is reputed to be 10,000 times as sweet as sucrose. 

Saccharin imparts a sweetness that is pleasant at the onset but is followed by a lingering, bitter aftertaste. Sensitivity to this bitterness varies from person to person. At high concentration, however, most people can detect the rather unpleasant aftertaste. Saccharin is syneigistic with other sweeteners of different chemical classes. For example, saccharin—cyclamate, saccharin—aspartame, saccharin—sucralose, and saccharin—alitame combinations all exert synergy to various degrees. The blends, as a rule, exhibit less aftertaste than each of the component sweeteners by themselves. 

Alitame [L- -aspartyl-/V-(2,2,4,4-tetramethyl-3-thioethanyl)-D-alaninamide] is an amino acid-based sweetener developed by Pfizer from L-aspartic acid, D-alanine, and an amine 2,2,4,4-tetraethylthioethanyl amine (Fig. 1). Its formula is CI4H2504N3S with a molecular weight of 331.06. It is produced under the brand name Aclame . It is a crystalline, odorless, nonhygro-scopic powder that is soluble in water (130 g/L at pH 5.6) and alcohol and significantly more stable than aspartame (Table 1). Alitame is 2000 times as sweet as sucrose and has a clean, sweet taste, with no unpleasant aftertaste. It blends with other sweeteners, such as acesulfame-K, saccharin, and cyclamate, to maximize the quality of sweetness (3,7-9). 

As might be expected, the search for an even better artificial sweetener continues. Alitame is a dipeptide formed from aspartic acid and alanine, with an unusual amide at the carboxylate end of the alanine. It is 2000 times as sweet as sucrose— 1 pound of alitame has the sweetening power of I ton of sucrose In addition, because an amide bond is more stable than an ester bond, alitame is more stable to hydrolysis than is aspartame. Therefore, alitame keeps its sweetness in aqueous solution better than aspar-... 

The increasing market demand for sweeteners resulted in the development of a number of chemicals. The major artificial sweeteners in the present market include acesulfame-K, alitame, aspartame, cyclamate, saccharin, and sucralose. Sweetness-intensity factors of several sweeteners compared with sucrose are given below ... 

Alitame [L-a-aspartyl-N-(2,2,4,4-tetramethyl-3-thietanyl)-D-alaninamide] is a sweetener based on an amino acid. It is a very intense sweetener, possessing a sweetening power of about 2000 times that of sucrose. It also exhibits a clean sweet taste similar to sucrose. Although it is metabolized, so little is needed that its caloric contribution is insignificant. Alitame is prepared from the amino acids, L-aspartic acid, D-alamine, and a novel amine [9]. 

While most mammals can detect and do prefer a wide variety of sweeteners, species vary considerably in their sweetener preference. Many of the compounds that taste sweet to humans are favored by a variety of mammalian species, including mice (Bachmanov et al. 2001a Fuller 1974 Kasahara et al. 1987 Lush 1989), hamsters (MacKinnon et al. 1999), rats (Nowhs et al. 1980), rabbits (Carpenter 1956), pigs (Nofre et al. 2002 Tinti et al. 2000), opossums (Pressman and Doolittle 1966), and primates (Fisher et al. 1965 Glaser et al. 1995, 1998 Haefeli et al. 1998 Nofre et al. 1996). However, species differences do exist. Rodents are indifferent to several artificial sweeteners (e.g., cyclamate, alitame, aspartame) (Hellekant and... 

Frank ME, Blizard DA (1999) Chorda tympani responses in two inbred strains of mice with different taste preferences. Physiol Behav 67 287-297 Fuller JL (1974) single-locus control of saccharin preference in mice. J Heredity 65 33-36 Galindo-Cuspinera V, Winnig M, Bufe B, Meyerhof W, Breslin PA (2006) A TAS1R receptor-based explanation of sweet water-taste . Nature 441 354-357 Glaser D, Tinti JM, Nofre C (1995) Evolution of the sweetness receptor in primates. I. Why does alitame taste sweet in all prosimians and simians, and aspartame only in Old World simians Chem Senses 20 573-584... 

A new sweetener, named Alitame by its inventors in your Research Division, is a dipeptide amide of L-aspartic acid and D-alanine. In contrast, aspartame, the amino acid-based sweetener currently approved by the FDA, is a dipeptide ester and contains L-phenylalanine instead of D-alanine. The New Products Department has tested the new material in a variety of uses and claims that it is stable enough for use in baked goods and has a longer shelf life than aspartame. It is also 12 times as sweet as aspartame and would not be harmful to people with the metabolic disorder, phenylketonuria, who must limit the intake of substances containing phenylalanine. Use is projected in foods, beverages, toiletries, and pharmaceuticals. 

Alitame [II] is nutritive, but due to its intense sweetness, the amounts used are small enough for it to be considered and classified as a nonnutritive sweetener. Alitame is formed from the amino acids L-aspartic acid and o-alanine with a novel amide moiety (formed from 2,2,4,4-tetra-methylthienanylamine). Alitame exhibits superior stability under a variety of conditions because of its unique amide group. Alitame has been approved... 

Perhaps the most successful and widely used artificial sweetener is aspartame, the methyl ester of a dipeptide formed from phenylalanine and aspartic acid. Aspartame is roughly 100 times as sweet as sucrose. It undergoes slow hydrolysis in solution, however, which limits its shelf life in products such as soft drinks. It also cannot be used for baking because it decomposes with heat. Furthermore, people with a genetic condition known as phenylketonuria cannot use aspartame because their metabolism causes a buildup of phenylpyruvic acid derived from aspartame. Accumulation of phenylpyruvic acid is harmful, especially to infants. Alitame, on the other hand, is a compound related to aspartame, but with improved properties. It is more... 

Amides of dipeptides consisting of L-aspartic acid and D-alanine are sweet (Table 8.11). The compound alitame is the N-3-(2,2,4,4-tetra-methyl)-thietanylamide of L-Asp-D-Ala (Formula 8.20) and with /sac,g(10) = 2000, it is a potential sweetener. 

Acesulfame potassium, one of the most recently approved sweeteners, is proving to be extremely popular in soft drinks because it has little aftertaste. Sucralose, another recently approved sweetener, is particularly useful in baked goods because of its stability at high temperatures. Alitame, marketed in some countries under the name Adame, is not approved for sale in the United States. It is some 2000 times as sweet as sucrose and, like acesufame-K, has no aftertaste. Of the five synthetic sweeteners listed in Table 21.2, only sucralose has clear structural resemblance to a carbohydrate, although it differs dramatically in containing three chlorine atoms. Aspartame and alitame are both dipeptides. 

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