NEOTAME

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 Search

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/29425148 | https://www.ncbi.nlm.nih.gov/pubmed/24741154 | https://www.ncbi.nlm.nih.gov/pubmed/25842566

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
[Simultaneous determination of six synthetic sweeteners in food by high performance liquid chromatography-tandem mass spectrometry].	2010-11	21381416
Retention behaviour of some high-intensity sweeteners on different SPE sorbents.	2010-10-15	20875571
Characterization of the beta-D-glucopyranoside binding site of the human bitter taste receptor hTAS2R16.	2010-09-03	20605788
Determination of neotame in beverages, cakes and preserved fruits by column-switching high-performance liquid chromatography.	2010-09	20526922
[Determination of five synthetic sweeteners in wines using high performance liquid chromatography-tandem mass spectrometry].	2010-08	21261041
Gain weight by "going diet?" Artificial sweeteners and the neurobiology of sugar cravings: Neuroscience 2010.	2010-06	20589192
Key amino acid residues involved in multi-point binding interactions between brazzein, a sweet protein, and the T1R2-T1R3 human sweet receptor.	2010-05-14	20302879
Positive allosteric modulators of the human sweet taste receptor enhance sweet taste.	2010-03-09	20173092
Standards of medical care in diabetes--2010.	2010-01	20042772
Analysis and occurrence of seven artificial sweeteners in German waste water and surface water and in soil aquifer treatment (SAT).	2009-07	19533103
Determination of nine intense sweeteners in foodstuffs by high-performance liquid chromatography and evaporative light-scattering detection: interlaboratory study.	2009-04-23	19382579
Simultaneous determination of nonnutritive sweeteners in foods by HPLC/ESI-MS.	2009-04-22	19275236
Analyses of sweet receptor gene (Tas1r2) and preference for sweet stimuli in species of Carnivora.	2009-04-16	19366814
[Simultaneous determination of artificial sweeteners in beverage by ultra performance liquid chromatography].	2009-01	19449553
Standards of medical care in diabetes--2009.	2009-01	19118286
Development of rebiana, a natural, non-caloric sweetener.	2008-07	18554769
The potential toxicity of artificial sweeteners.	2008-06	18604921
[Simultaneous determination of neotame, alitame and aspartame in foods by HPLC].	2008-02	18344656
The binding site for neohesperidin dihydrochalcone at the human sweet taste receptor.	2007-10-12	17935609
Simultaneous determination of nine intense sweeteners in foodstuffs by high performance liquid chromatography and evaporative light scattering detection--development and single-laboratory validation.	2007-07-20	17540386
Artificial sweeteners: no calories...sweet!	2007-01-25	17243285
Taste responses to sweet stimuli in alpha-gustducin knockout and wild-type mice.	2006-07	16740645
The G protein-coupled receptor subset of the chicken genome.	2006-06-02	16741557
The heterodimeric sweet taste receptor has multiple potential ligand binding sites.	2006	17168764
Quantitation of crystalline and amorphous forms of anhydrous neotame using 13C CPMAS NMR spectroscopy.	2005-12	16258988
Artificial sweeteners--do they bear a carcinogenic risk?	2004-10	15367404
Different functional roles of T1R subunits in the heteromeric taste receptors.	2004-09-28	15353592
Position of the American Dietetic Association: use of nutritive and nonnutritive sweeteners.	2004-02	14760578
[Effect of food additive Neotame (N-[N-(3,3-dimethylbutyl)-L-alpha-aspartyl]-L-phenylalanine-1-methyl) on glucose level in blood of patients with diabetes mellitus type 2].	2004	15685854
Evaluation of certain food additives and contaminants.	2004	15354533
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.	2003-10	14550756
Food consumption and body weight changes with neotame, a new sweetener with intense taste: differentiating effects of palatability from toxicity in dietary safety studies.	2003-10	14550755
Crystal structure of neotame anhydrate polymorph G.	2002-10	12425475
Neotame anhydrate polymorphs. II: Quantitation and relative physical stability.	2002-09	12403060
Conformational flexibility and hydrogen-bonding patterns of the neotame molecule in its various solid forms.	2002-09	12210051
Neotame - a new artificial sweetener.	2002-08-19	12205430
Dehydration kinetics of neotame monohydrate.	2002-06	12115842
Neotame anhydrate polymorphs I: preparation and characterization.	2002-03	11934241
Structure, dynamics, and stability of beta-cyclodextrin inclusion complexes of aspartame and neotame.	2001-04	11308366
Modifying the temporal profile of the high-potency sweetener neotame.	2001-02	11262029

Patents

Name

Type

Language

E 961

Preferred Name

English

NEOTAME

Official Name

English

NEOTAME [FHFI]

Common Name

English

N-(N-(3,3-DIMETHYLBUTYL)-L-.ALPHA.-ASPARTYL)-L-PHENYLALANINE 1-METHYL ESTER

Common Name

English

NC-00723

Code

English

INS-961

Code

English

NEOTAME [USP-RS]

Common Name

English

INS NO.961

Code

English

NEOTAME [MI]

Common Name

English

NEOTAME [MART.]

Common Name

English

L-PHENYLALANINE, N-(N-(3,3-DIMETHYLBUTYL)-L-.ALPHA.-ASPARTYL)-1-METHYL ESTER

Common Name

English

NEOTAME [II]

Common Name

English

MIRASEE 200

Common Name

English

NEOTAME [FCC]

Common Name

English

E-961

Code

English

Classification Tree Code System Code

CODEX ALIMENTARIUS (GSFA)

INS-961