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Details

Stereochemistry ABSOLUTE
Molecular Formula C14H25N3O4S
Molecular Weight 331.431
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ALITAME ANHYDROUS

SMILES

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

InChI

InChIKey=IVBOUFAWPCPFTQ-SFYZADRCSA-N
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

HIDE SMILES / InChI
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
Solvent-free enzymatic synthesis of alitame precursor using eutectic substrate mixtures.
2001 May 7
Artificial sweeteners - a review.
2014 Apr
The role of artificial and natural sweeteners in reducing the consumption of table sugar: A narrative review.
2017 Apr
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
Name Type Language
ALITAME ANHYDROUS
Common Name English
INS NO.956(ALITAME ANHYDROUS)
Common Name English
ALITAME [MART.]
Common Name English
(3S)-AMINO-N-((1R)-1-((2,2,4,4-TETRAMETHYL-3-THIETANYL)CARBAMOYL)ETHYL)SUCCINAMIC ACID
Common Name English
D-ALANINAMIDE, L-.ALPHA.-ASPARTYL-N-(2,2,4,4-TETRAMETHYL-3-THIETANYL)-
Systematic Name English
INS-956(ALITAME ANHYDROUS)
Common Name English
ALITAME [MI]
Common Name English
E-956(ALITAME ANHYDROUS)
Common Name English
Classification Tree Code System Code
CODEX ALIMENTARIUS (GSFA) INS-956
Created by admin on Fri Dec 15 16:17:41 GMT 2023 , Edited by admin on Fri Dec 15 16:17:41 GMT 2023
NCI_THESAURUS C283
Created by admin on Fri Dec 15 16:17:41 GMT 2023 , Edited by admin on Fri Dec 15 16:17:41 GMT 2023
Code System Code Type Description
CAS
80863-62-3
Created by admin on Fri Dec 15 16:17:41 GMT 2023 , Edited by admin on Fri Dec 15 16:17:41 GMT 2023
PRIMARY
PUBCHEM
64763
Created by admin on Fri Dec 15 16:17:41 GMT 2023 , Edited by admin on Fri Dec 15 16:17:41 GMT 2023
PRIMARY
EPA CompTox
DTXSID3043780
Created by admin on Fri Dec 15 16:17:41 GMT 2023 , Edited by admin on Fri Dec 15 16:17:41 GMT 2023
PRIMARY
MERCK INDEX
m1510
Created by admin on Fri Dec 15 16:17:41 GMT 2023 , Edited by admin on Fri Dec 15 16:17:41 GMT 2023
PRIMARY Merck Index
NCI_THESAURUS
C77135
Created by admin on Fri Dec 15 16:17:41 GMT 2023 , Edited by admin on Fri Dec 15 16:17:41 GMT 2023
PRIMARY
FDA UNII
PCE8DAE750
Created by admin on Fri Dec 15 16:17:41 GMT 2023 , Edited by admin on Fri Dec 15 16:17:41 GMT 2023
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