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

Molecular Formula	C20H30N2O5
Molecular Weight	378.4626
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

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
Neotame - a new artificial sweetener.	2002 Aug 19	12205430
Dehydration kinetics of neotame monohydrate.	2002 Jun	12115842
Neotame anhydrate polymorphs I: preparation and characterization.	2002 Mar	11934241
Crystal structure of neotame anhydrate polymorph G.	2002 Oct	12425475
Neotame anhydrate polymorphs. II: Quantitation and relative physical stability.	2002 Sep	12403060
Conformational flexibility and hydrogen-bonding patterns of the neotame molecule in its various solid forms.	2002 Sep	12210051
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	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 Oct	14550755
Evaluation of certain food additives and contaminants.	2004	15354533
Artificial sweeteners--do they bear a carcinogenic risk?	2004 Oct	15367404
Quantitation of crystalline and amorphous forms of anhydrous neotame using 13C CPMAS NMR spectroscopy.	2005 Dec	16258988
Development of rebiana, a natural, non-caloric sweetener.	2008 Jul	18554769
Simultaneous determination of nonnutritive sweeteners in foods by HPLC/ESI-MS.	2009 Apr 22	19275236
[Simultaneous determination of artificial sweeteners in beverage by ultra performance liquid chromatography].	2009 Jan	19449553
Determination of nine intense sweeteners in foodstuffs by high-performance liquid chromatography and evaporative light-scattering detection: interlaboratory study.	2009 Jan-Feb	19382579
Analyses of sweet receptor gene (Tas1r2) and preference for sweet stimuli in species of Carnivora.	2009 Jul-Aug	19366814
Positive allosteric modulators of the human sweet taste receptor enhance sweet taste.	2010 Mar 9	20173092
Key amino acid residues involved in multi-point binding interactions between brazzein, a sweet protein, and the T1R2-T1R3 human sweet receptor.	2010 May 14	20302879
[Simultaneous determination of six synthetic sweeteners in food by high performance liquid chromatography-tandem mass spectrometry].	2010 Nov	21381416

Patents

Substance Class	Chemical Created by `admin` on `Fri Dec 15 17:36:00 GMT 2023` Edited by `admin` on `Fri Dec 15 17:36:00 GMT 2023`
Record UNII	VJ597D52EX
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

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

E 961

Code

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 [INCI]

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