Sweeteners alitame

Aspartame (L-aspartyl-L-phenylalanine methyl ester [22859-47-0]) is about 200 times sweeter than sucrose. The Acceptable Daily Intake (ADI) has been estabflshed by JECFA as 40 mg/kg/day. Stmcture-taste relationship of peptides has been reviewed (223). Demand for L-phenylalanine and L-aspartic acid as the raw materials for the synthesis of aspartame has been increasing. D-Alanine is one component of a sweetener "Alitame" (224). 

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... 

In order to develop an enzymatic method to S5mthesize D-alanine N-alkyl amide, which is found in the structure of an artificial sweetener, alitame (L-a-aspartyl-N-(2,2,4,4-tetramethyl-3-thietanyl)-D-alanine amide), we screened microorganisms for an enzyme that catalyzes o-stereospecific amino acid amide hydrolysis [1]. 

Alitame. A new group of aspartyl-dipeptide sweeteners became known to the pubHc in 1983 (95). Alitame [80863-62-3] L-aspartyl-D-alanine... 

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). 

Sweeteners can be roughly divided into two groups bulk and intense sweeteners. Prodolliet (1996) and Gloria (2000) reviewed thoroughly the analysis and properties of intense sweeteners acesulfame-K, alitame, cyclamate, aspartame, glycyrrhizin, neohesperidin DC, saccharin, stevioside, sucralose and thaumatin. They are generally used in low calorie products such as diet... 

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

What problem arises in using alitame as artificial sweetener ... 

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. A new group of aspartyl-dipeptide sweeteners became known to the public in 1983 (95). Alitame [80863-62-3 ], l- as p a rtyl- d - alanine A -(2,2,4,4-tetramethylthietan-3-yl)armde (16), was selected for commercial development. In 1986 Pfizer filed a food additive petition with the FDA. As of December, 1996, it was still pending. Alitame was approved for use as a sweetener by Australia in 1993, by China, Mexico, and New Zealand in 1994, by Indonesia in 1995, and by Colombia in 1996. 

Fig-1 Chemical structures of the intense sweeteners saccharin, sodium cyclamate, acesulfame-K, aspartame, alitame, dulcin, sucralose, and neohesperidin dihydrochalcone. 

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). 

Formulators in most markets now have a wide range of sweeteners available to use either alone or in combination. As Figures 4.1 and 4.2 show, the main intense sweeteners in use in soft drinks today are acesulfame K, aspartame, saccharin and cyclamate. Currently of less importance commercially (either because they are new to the market or because they have not found significant use in soft drinks), but still approved for use in soft drinks in some markets, are thaumatin, neohesperidin diliy-diochalcones, alitame, stevioside, sucralose and neotame. 

Alitame is the generic name for L-a-aspartyl-N-(2,2,4,4-tetramethyl-3-thetanyl)-D-alaninamide hydrate. Pfizer patented the sweetener in 1980 (Pfizer, 1980). It is a white, non-hygroscopic crystalline powder with good solubility in... 

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]. 

Alitame is an intense sweetening agent developed in the early 1980s and is approximately 2000 times sweeter than sucrose. It has an insignificant energy contribution of 6 kj (1.4 kcal) per gram of alitame. 

Alitame is a relatively new intense sweetening agent used primarily in foods and confectionary. It is generally regarded as a relatively nontoxic and nonirritant material. 

Hendrick ME. Alitame. In Nabors L, Gelardi R, eds. Alternative Sweeteners. New York Marcel Dekker, 1991 29-38. 

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... 

Monosodium Glutamate Polysaccharides from Microalgae Alitame Sweetener Pharmaceuticals... 

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. 

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