Alitame is a white nonhygroscopic crystalline powder; odorless or having a slight characteristic odor.
Related Substances: Acesulfame potassium; aspartame; saccharin; saccharin sodium; sodium cyclamate.
Synonyms: Aclame; L-aspartyl-D-alanine-N-(2,2,4,4-tetramethylthietan-3-yl)amide; 3-(L-aspartyl-D-alaninamido)-2,2,4,4-tetramethylthietane.
Chemical Name and CAS Registry Number
- L-a-Aspartyl-N-(2, 2, 4, 4-tetramethyl-3-thietanyl)-D-alaninamide anhydrous [80863-62-3]
- L-a-Aspartyl-N-(2, 2, 4, 4-tetramethyl-3-thietanyl)-D-alaninamide hydrate [99016-42-9]
Empirical Formula and Molecular Weight
- C14H25N3O4S 331.44 (for anhydrous)
- C14H25N3O4S21=2H2O 376.50 (for hydrate)
- Sweetening agent.
Applications in Pharmaceutical Formulation or Technology
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 currently primarily used in a wide range of foods and beverages at a maximum level of 40–300 mg/kg.
- Acidity/alkalinity pH = 5–6 (5% w/v aqueous solution)
- Isoelectric point pH 5.6
- Melting point 136–1478C
Method of Manufacture
Alitame may be synthesized by a number of routes. For example, 3-(D-alaninamido)-2,2,4,4-tetramethylthietane is dissolved in water and L-aspartic acid N-thiocarboxyanhydride is then added in portions with vigorous stirring, maintaining the pH of 8.5–9.5. The pH is then adjusted to 5.5 and p-toluenesulfonic acid monohydrate is added over a period of one hour. The precipitated crystalline p-toluenesulfonate salt is collected by filtration.
To obtain alitame from its salt, a mixture of Amberlite LA-1 (liquid anion exchange resin), dichloromethane, deionized water, and the salt is stirred for one hour, resulting in two clear layers. The aqueous layer is treated with carbon, clarified by filtration, and cooled to crystallize alitame.
Alternatively, tetramethylthietane amine is condensed with an N-protected form of D-alanine to give alanyl amide. This is then coupled to a protected analogue of L-aspartic acid to give a crude form of alitame. The crude product is then purified.