Alitame

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Alitame
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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
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3D model (JSmol)
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  • 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 checkY
    Key: IVBOUFAWPCPFTQ-SFYZADRCSA-N checkY
  • 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
  • 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
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).

Template:Chembox Footer/trackingTemplate:Short description

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 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 Danisco has withdrawn its petition for using alitame as a sweetening agent or flavoring in food in US.[3]

Sweeny also addresses a compound with a sweetness of 1200 x sucrose in his review,[4] in U.S. patent 4411925 based on an NH-CH(cyclopropyl)tert-butyl (Ex 6). Ex 5, with NH-CH(cyclopropyl)2 is also 1200 x sucrose. These are good basis for 2nd class picks. Ex 16 is for Alitame proper. Although, in Ex 17, oxidation to the sulfonyl can reduce activity to 1000.

References

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  1. ^ Page Module:Citation/CS1/styles.css has no content.Ellis, J. W. (1995). "Overview of Sweeteners". Journal of Chemical Education. 72 (8): 671–675. Bibcode:1995JChEd..72..671E. doi:10.1021/ed072p671.
  2. ^ Page Module:Citation/CS1/styles.css has no content.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. pp. 5. ISBN 978-0-470-00955-0. OCLC 173182689.
  3. ^ Page Module:Citation/CS1/styles.css has no content."Notice of withdrawal of petition: docket No. FDA-1986-F-0277 (formerly docket No. 1986F-0364)" (PDF). Food and Drug Administration. Archived from the original (PDF) on September 10, 2008.
  4. ^ Page Module:Citation/CS1/styles.css has no content.Sweeny, James G.; D'Angelo, Lihong L.; Ricks, Edith A.; Iacobucci, Guillermo A. (1995). "Discovery and Synthesis of a New Series of High-Potency L-Aspartyl-D-.alpha.-aminoalkanoyl-(S)-.alpha.-alkylbenzylamide Sweeteners". Journal of Agricultural and Food Chemistry. 43 (8): 1969–1976. Bibcode:1995JAFC...43.1969S. doi:10.1021/jf00056a003. ISSN 0021-8561.

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