View source for Alitame

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{{chembox
| Verifiedfields = changed
| verifiedrevid = 477317514
| ImageFile=alitame.svg
| ImageSize=200px
| IUPACName= <small>(3S)-3-amino-4-[ [(1R)-1-methyl-2-oxo-2-[(2,2,4,4-tetramethyl-3-thietanyl)amino]ethyl]amino]-4-oxobutanoic acid</small>
| OtherNames=L-alpha-Aspartyl-N-(2,2,4,4-tetramethyl-3-thietanyl)-D-alaninamide
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 58297
| 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
| InChIKey = IVBOUFAWPCPFTQ-SFYZADRCBL
| SMILES1 = O=C(NC1C(SC1(C)C)(C)C)[C@H](NC(=O)[C@@H](N)CC(=O)O)C
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = IVBOUFAWPCPFTQ-SFYZADRCSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo= 80863-62-3
| CASNo_Comment =(anhydrous)
| CASNo1_Ref = {{cascite|correct|CAS}}
| CASNo1 = 99016-42-9
| CASNo1_Comment =(hydrate)
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 2104004
| PubChem= 64763
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = PCE8DAE750
| UNII_Comment = (anhydrous)
| UNII1_Ref = {{fdacite|correct|FDA}}
| UNII1 = 6KI9M51JOG
| UNII1_Comment = (hydrate)

| SMILES=CC(C(=O)NC1C(SC1(C)C)(C)C)NC(=O)C(CC(=O)O)N
  }}
|Section2       = {{Chembox Properties
| Formula       = C<sub>14</sub>H<sub>25</sub>N<sub>3</sub>O<sub>4</sub>S
| MolarMass     = 331.431
| Appearance    =
| Density       =
| MeltingPt     =
| BoilingPt     =
| Solubility    =
  }}
|Section3        ={{Chembox Hazards
| MainHazards    =
| FlashPt        =
| AutoignitionPt =
  }}
}}

'''Alitame''' is an [[aspartic acid]]-containing dipeptide [[Sugar substitute|sweetener]]. It was developed by [[Pfizer]] in the early 1980s and currently marketed in some countries under the brand name '''Aclame'''.<ref>{{ cite journal | author = Ellis, J. W. | title = Overview of Sweeteners | journal = Journal of Chemical Education | year = 1995 | volume = 72 | issue = 8 | pages = 671–675 | doi = 10.1021/ed072p671 | bibcode = 1995JChEd..72..671E }}</ref> 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),<ref>{{cite book |author=Laura Halpin Rinsky |author2=Glenn Rinsky |title=The Pastry Chef's Companion: A Comprehensive Resource Guide for the Baking and Pastry Professional |url=https://archive.org/details/pastrychefscompa00rins |url-access=limited |publisher=John Wiley & Sons |location=Chichester |year=2009 |pages=[https://archive.org/details/pastrychefscompa00rins/page/n14 5] |isbn=978-0-470-00955-0 |oclc=173182689}}</ref> 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]].<ref>{{ cite web | url = https://www.fda.gov/OHRMS/DOCKETS/98fr/E8-13998.pdf | archive-url = https://web.archive.org/web/20080910124120/http://www.fda.gov/OHRMS/DOCKETS/98fr/E8-13998.pdf | url-status = dead | archive-date = September 10, 2008 | title = Notice of withdrawal of petition: docket No. FDA-1986-F-0277 (formerly docket No. 1986F-0364) | publisher = Food and Drug Administration }}</ref>

Sweeny also addresses a compound with a sweetness of 1200 x sucrose in his review,<ref name="SweenyD'Angelo1995">{{cite journal|last1=Sweeny|first1=James G.|last2=D'Angelo|first2=Lihong L.|last3=Ricks|first3=Edith A.|last4=Iacobucci|first4=Guillermo A.| title=Discovery and Synthesis of a New Series of High-Potency L-Aspartyl-D-.alpha.-aminoalkanoyl-(S)-.alpha.-alkylbenzylamide Sweeteners|journal=Journal of Agricultural and Food Chemistry|volume=43|issue=8|year=1995|pages=1969–1976|issn=0021-8561|doi=10.1021/jf00056a003}}</ref> in {{US 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==
{{Reflist}}

==External links==
*{{Commons category-inline}}
*[https://www.modernfit.com/food/is-sucralose-keto-friendly/ Is Sucralose Keto Friendly?]

{{E number infobox 950-969}}

[[Category:Peptides]]
[[Category:Sugar substitutes]]