Alitame

Alitame

Names
IUPAC name (3S)-3-amino-4-[ [(1R)-1-methyl-2-oxo-2-[(2,2,4,4-tetramethyl-3-thietanyl)amino]ethyl]amino]-4-oxobutanoic acid
Other names L-alpha-Aspartyl-N-(2,2,4,4-tetramethyl-3-thietanyl)-D-alaninamide
Identifiers
CAS Number	80863-62-3
ChEMBL	ChEMBL2104004
ChemSpider	58297
Jmol interactive 3D	Image Image
PubChem	64763
UNII	6KI9M51JOG
InChI InChI=1S/C14H25N3O4S/c1-7(16-11(21)8(15)6-9(18)19)10(20)17-12-13(2,3)22-14(12,4)5/h7-8,12H,6,15H2,1-5H3,(H,16,21)(H,17,20)(H,18,19)/t7-,8+/m1/s1 Key: IVBOUFAWPCPFTQ-SFYZADRCSA-N InChI=1/C14H25N3O4S/c1-7(16-11(21)8(15)6-9(18)19)10(20)17-12-13(2,3)22-14(12,4)5/h7-8,12H,6,15H2,1-5H3,(H,16,21)(H,17,20)(H,18,19)/t7-,8+/m1/s1 Key: IVBOUFAWPCPFTQ-SFYZADRCBL
SMILES CC(C(=O)NC1C(SC1(C)C)(C)C)NC(=O)C(CC(=O)O)N O=C(NC1C(SC1(C)C)(C)C)[C@H](NC(=O)[C@@H](N)CC(=O)O)C
Properties
Chemical formula	C14H25N3O4S
Molar mass	331.431
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Alitame is an aspartic acid-containing dipeptide sweetener. It was developed by Pfizer in the early 1980s and currently marketed in some countries under the brand name Aclame.^[1] Most dipeptides are not sweet, but the unexpected discovery of aspartame in 1965 led to a search for similar compounds that shared its sweetness. Alitame is one such second-generation dipeptide sweetener. Neotame, developed by the owners of the NutraSweet brand, is another.

Alitame is about 2000 times sweeter than sucrose (table sugar),^[2] about 10 times sweeter than aspartame, and has no aftertaste. Its half-life under hot or acidic conditions is about twice as long as aspartame's, although some other artificial sweeteners, including saccharin and acesulfame potassium, are more stable yet. Unlike aspartame, alitame does not contain phenylalanine, and can therefore be used by people with phenylketonuria.

Alitame has approved for use in Mexico, Australia, New Zealand and China. Danisco has withdrawn its petition for using alitame as a sweetening agent or flavoring in food in USA.^[3]

Synthesis

Alitame synthesis: U.S. Patent 5,874,121 C.f. Lednicer book 6.

• In U.S. Patent 4,411,925, alanine is protected with trimethylchlorosilane.

References

1. Ellis, J. W. (1995). "Overview of Sweeteners". Journal of Chemical Education 72 (8): 671–675. doi:10.1021/ed072p671.
2. Laura Halpin Rinsky; Glenn Rinsky (2009). The Pastry Chef's Companion: A Comprehensive Resource Guide for the Baking and Pastry Professional. Chichester: John Wiley & Sons. p. 5. ISBN 0-470-00955-1. OCLC 173182689.
3. "Notice of withdrawal of petition: docket No. FDA-1986-F-0277 (formerly docket No. 1986F-0364)" (pdf). Food and Drug Administration.