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Details

Stereochemistry ABSOLUTE
Molecular Formula 2C14H25N3O4S.5H2O
Molecular Weight 752.938
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ALITAME

SMILES

O.O.O.O.O.C[C@@H](NC(=O)[C@@H](N)CC(O)=O)C(=O)NC1C(C)(C)SC1(C)C.C[C@@H](NC(=O)[C@@H](N)CC(O)=O)C(=O)NC2C(C)(C)SC2(C)C

InChI

InChIKey=NUFKRGBSZPCGQB-FLBSXDLDSA-N
InChI=1S/2C14H25N3O4S.5H2O/c2*1-7(16-11(21)8(15)6-9(18)19)10(20)17-12-13(2,3)22-14(12,4)5;;;;;/h2*7-8,12H,6,15H2,1-5H3,(H,16,21)(H,17,20)(H,18,19);5*1H2/t2*7-,8+;;;;;/m11...../s1

HIDE SMILES / InChI

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C14H25N3O4S
Molecular Weight 331.431
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Alitame [l-α-aspartyl-N-(2,2,4,4-tetramethyl-3-thioethanyl)-d-alaninamide] is an amino acid-based sweetener developed by Pfizer Central Research from l-aspartic acid, d-alanine, and 2,2,4,4-tetraethylthioethanyl amine. A terminal amide group instead of the methyl ester constituent of aspartame was used to improve the hydrolytic stability. The incorporation of d-alanine as a second amino acid in place of l-phenylalanine has resulted in optimum sweetness. The increased steric and lipophilic bulk on a small ring with a sulfur derivative has provided a very sweet product and good taste qualities. Alitame is noncariogenic. From an oral intake, 7–22% is unabsorbed and excreted in the feces. The remainder is hydrolyzed to aspartic acid and alanine amide. The aspartic acid is normally metabolized, and the alanine amide is excreted in the urine as a sulfoxide isomer, sulfone, or conjugated with glucuronic acid. U.S. Food and Drug Administration has approved alitame for use as per acceptable daily intake (ADI) value.

Approval Year

PubMed

PubMed

TitleDatePubMed
Patents

Patents

Sample Use Guides

An acceptable daily intake (ADI) of 0–1 mg per kilogram of body weight was allocated. The estimated daily intake is 0.34 mg per kilogram of body weight, which represents the amount if alitame is the only sweetener in the diet.
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:13:31 GMT 2023
Edited
by admin
on Fri Dec 15 16:13:31 GMT 2023
Record UNII
6KI9M51JOG
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ALITAME
FCC   HSDB   USAN  
USAN  
Official Name English
E-956(ALITAME)
Common Name English
ALITAME [USP-RS]
Common Name English
ALITAME HYDRATE
Common Name English
ALITAME [USAN]
Common Name English
ALITAME [HSDB]
Common Name English
ACLAME
Brand Name English
(3S)-Amino-N-[(1R)-1-[(2,2,4,4-tetramethyl-3-thietanyl)carbamoyl]ethyl]succinamic acid hydrate (2:5)
Systematic Name English
D-ALANINAMIDE, L-.ALPHA.-ASPARTYL-N-(2,2,4,4-TETRAMETHYL-3-THIETANYL)-, HYDRATE (2:5)
Common Name English
CP-54,802
Code English
ALITAME [FCC]
Common Name English
INS-956(ALITAME)
Common Name English
CP-54802
Code English
INS NO.956(ALITAME)
Common Name English
Classification Tree Code System Code
CODEX ALIMENTARIUS (GSFA) INS-956
Created by admin on Fri Dec 15 16:13:31 GMT 2023 , Edited by admin on Fri Dec 15 16:13:31 GMT 2023
NCI_THESAURUS C283
Created by admin on Fri Dec 15 16:13:31 GMT 2023 , Edited by admin on Fri Dec 15 16:13:31 GMT 2023
Code System Code Type Description
PUBCHEM
20055408
Created by admin on Fri Dec 15 16:13:31 GMT 2023 , Edited by admin on Fri Dec 15 16:13:31 GMT 2023
PRIMARY
HSDB
7825
Created by admin on Fri Dec 15 16:13:31 GMT 2023 , Edited by admin on Fri Dec 15 16:13:31 GMT 2023
PRIMARY
RS_ITEM_NUM
1012848
Created by admin on Fri Dec 15 16:13:31 GMT 2023 , Edited by admin on Fri Dec 15 16:13:31 GMT 2023
PRIMARY
FDA UNII
6KI9M51JOG
Created by admin on Fri Dec 15 16:13:31 GMT 2023 , Edited by admin on Fri Dec 15 16:13:31 GMT 2023
PRIMARY
USAN
Y-33
Created by admin on Fri Dec 15 16:13:31 GMT 2023 , Edited by admin on Fri Dec 15 16:13:31 GMT 2023
PRIMARY
CAS
1269188-34-2
Created by admin on Fri Dec 15 16:13:31 GMT 2023 , Edited by admin on Fri Dec 15 16:13:31 GMT 2023
NON-SPECIFIC STOICHIOMETRY
CAS
99016-42-9
Created by admin on Fri Dec 15 16:13:31 GMT 2023 , Edited by admin on Fri Dec 15 16:13:31 GMT 2023
PRIMARY
MESH
C082016
Created by admin on Fri Dec 15 16:13:31 GMT 2023 , Edited by admin on Fri Dec 15 16:13:31 GMT 2023
PRIMARY
ChEMBL
CHEMBL2104004
Created by admin on Fri Dec 15 16:13:31 GMT 2023 , Edited by admin on Fri Dec 15 16:13:31 GMT 2023
PRIMARY
NCI_THESAURUS
C74194
Created by admin on Fri Dec 15 16:13:31 GMT 2023 , Edited by admin on Fri Dec 15 16:13:31 GMT 2023
PRIMARY
EPA CompTox
DTXSID1035028
Created by admin on Fri Dec 15 16:13:31 GMT 2023 , Edited by admin on Fri Dec 15 16:13:31 GMT 2023
PRIMARY
WIKIPEDIA
ALITAME
Created by admin on Fri Dec 15 16:13:31 GMT 2023 , Edited by admin on Fri Dec 15 16:13:31 GMT 2023
PRIMARY
Related Record Type Details
ANHYDROUS->SOLVATE