Title: Alitame
CAS Registry Number: 80863-62-3
CAS Name: L-a-Aspartyl-N-(2,2,4,4-tetramethyl-3-thietanyl)-D-alaninamide
Additional Names: L-aspartyl-D-alanine-N-(2,2,4,4-tetramethylthietan-3-yl)amide; 3-(L-aspartyl-D-alaninamido)-2,2,4,4-tetramethylthietane
Manufacturers' Codes: CP-54802
Trademarks: Aclame (Danisco)
Molecular Formula: C14H25N3O4S
Molecular Weight: 331.43
Percent Composition: C 50.73%, H 7.60%, N 12.68%, O 19.31%, S 9.67%
Literature References: Dipeptide amide reported to be approx 2000 times sweeter than sucrose. Prepn: T. M. Brennan, M. E. Hendrick, EP 34876; eidem, US 4411925 (1981, 1983 both to Pfizer). Conformational analysis: R. D. Feinstein et al., J. Am. Chem. Soc. 113, 3467 (1991). Review of development and uses: R. C. Glowaky et al., ACS Symp. Ser. 450, 57-67 (1991); of chemical and physical properties: M. E. Hendrick et al., in Advances in Sweeteners, T. H. Grenby, Ed. (Blackie, Glasgow, 1996) pp 226-239; M. H. Auerbach et al., in Alternative Sweeteners, L. O'Brien Nabors, Ed. (Marcel Dekker, Inc., New York, 2001) pp 31-40.
Properties: White, crystalline, non-hygroscopic powder, mp 136-147°. Faint, characteristic odor; intensely sweet taste. [a]D25 +40 to +50° (c = 1 in water). pI 5.6. Soly at 25° (% w/v): water (pH 5.6) 13.1; methanol 41.9; ethanol 61.0; propylene glycol 53.7; chloroform 0.02; n-heptane 0.001.
Melting point: mp 136-147°
Optical Rotation: [a]D25 +40 to +50° (c = 1 in water)
Use: Non-nutritive sweetener. |