3‐Amino‐3‐({1‐[(2,2,4,4‐tetramethylthietan‐3‐ yl)carbamoyl]ethyl}carbamoyl)propanoic acid

Alitame is a white, non-hygroscopic crystalline powder that is odorless or has a slight characteristic odor. It has a sweet taste and is approximately 2,000 times sweeter than sucrose. Its flavor is similar to that of sucrose, with no bitter aftertaste or metallic taste, a rapid onset of sweetness, and a faint lingering sweetness. It does not absorb water. It is readily soluble in ethanol (61%), glycerol (53.7%), methanol (41.9%), and water (13.1%), and slightly soluble in chloroform. It exhibits good heat resistance and good resistance to acids and alkalis.

역사Alitame, L-α-aspartyl-D-alanine N-(2,2,4,4-tetra methylthietan-3-yl)amide (5), was developed by Pfizer, but is owned by Danisco now. In 1986, Pfizer filed a food additive petition with the FDA. As of 2006, 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.

용도Alitame is a dipeptide amide derivative of aspartic acid used as an artificial sweetener. Alitame is about ten times sweeter than Aspartame (A790015) with a half life about twice as long.

생산 방법Alitame 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 anNprotected 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.