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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H30N2O5
Molecular Weight 378.4626
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NEOTAME

SMILES

COC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@H](CC(O)=O)NCCC(C)(C)C

InChI

InChIKey=HLIAVLHNDJUHFG-HOTGVXAUSA-N
InChI=1S/C20H30N2O5/c1-20(2,3)10-11-21-15(13-17(23)24)18(25)22-16(19(26)27-4)12-14-8-6-5-7-9-14/h5-9,15-16,21H,10-13H2,1-4H3,(H,22,25)(H,23,24)/t15-,16-/m0/s1

HIDE SMILES / InChI

Molecular Formula C20H30N2O5
Molecular Weight 378.4626
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Neotame is a derivative of a dipeptide compound of the amino acids - aspartic acid and phenylalanine. Neotame has been developed as a sweetener with a high degree of sweetness and is obtained by N-alkylating aspartame. Its degree of sweetness varies according to the kind of food and blend composition. It is 7000 to 13,000 times and about 30 to 60 times sweeter than sugar and aspartame respectively. Neotame is rapidly metabolized, completely eliminated and does not accumulate in the body. The major metabolic pathway of neotame is hydrolysis of the methyl ester by esterase which is present throughout the body. This yields de-esterified neotame, the major metabolite and a significant amount of methanol. Due to the presence of the 3-3-di-methylbutyl group, peptidases which would typically break the peptide bond between the aspartic acid and phenylalanine moieties are essentially blocked, thus reducing the availability of phenylalanine. Neotame was approved by the USFDA as a general purpose sweetener in July 2002

Approval Year

PubMed

Substance Class Chemical
Record UNII
VJ597D52EX
Record Status Validated (UNII)
Record Version