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
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
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
Title | Date | PubMed |
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Modifying the temporal profile of the high-potency sweetener neotame. | 2001 Feb |
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Neotame - a new artificial sweetener. | 2002 Aug 19 |
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Neotame anhydrate polymorphs I: preparation and characterization. | 2002 Mar |
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Long-term food consumption and body weight changes in neotame safety studies are consistent with the allometric relationship observed for other sweeteners and during dietary restrictions. | 2003 Oct |
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Food consumption and body weight changes with neotame, a new sweetener with intense taste: differentiating effects of palatability from toxicity in dietary safety studies. | 2003 Oct |
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Artificial sweeteners--do they bear a carcinogenic risk? | 2004 Oct |
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The G protein-coupled receptor subset of the chicken genome. | 2006 Jun 2 |
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Simultaneous determination of nine intense sweeteners in foodstuffs by high performance liquid chromatography and evaporative light scattering detection--development and single-laboratory validation. | 2007 Jul 20 |
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Standards of medical care in diabetes--2009. | 2009 Jan |
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Determination of nine intense sweeteners in foodstuffs by high-performance liquid chromatography and evaporative light-scattering detection: interlaboratory study. | 2009 Jan-Feb |
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[Determination of five synthetic sweeteners in wines using high performance liquid chromatography-tandem mass spectrometry]. | 2010 Aug |
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[Simultaneous determination of six synthetic sweeteners in food by high performance liquid chromatography-tandem mass spectrometry]. | 2010 Nov |
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Classification Tree | Code System | Code | ||
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CODEX ALIMENTARIUS (GSFA) |
INS-961
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JECFA EVALUATION |
INS-961
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NCI_THESAURUS |
C283
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CFR |
21 CFR 172.829
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SUB119863
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NEOTAME
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1460204
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VJ597D52EX
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DTXSID50167950
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100000143306
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VJ597D52EX
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m7820
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9810996
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7965
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165450-17-9
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C81625
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1367111
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PRIMARY | RxNorm |
SUBSTANCE RECORD