Neotame

Neotame

Names
IUPAC name (3S)-3-(3,3-Dimethylbutylamino)-4-[[(2S)-1-methoxy-1-oxo-3-phenylpropan-2-yl]amino]-4-oxobutanoic acid
Other names E961; N-(N-(3,3-Dimethylbutyl)-L-α-aspartyl)-L-phenylalanine 1-methyl ester
Identifiers
CAS Number	165450-17-9 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:83503 N
ChemSpider	7986751 N
ECHA InfoCard	100.109.344
E number	E961 (glazing agents, ...)
PubChem	9810996
UNII	VJ597D52EX Y
InChI 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 N Key: HLIAVLHNDJUHFG-HOTGVXAUSA-N N InChI=1/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 Key: HLIAVLHNDJUHFG-HOTGVXAUBG
SMILES CC(C)(C)CCN[C@@H](CC(=O)O)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)OC
Properties
Chemical formula	C20H30N2O5
Molar mass	378.47 g·mol−1
Hazards
NFPA 704	1 0 0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Neotame is an artificial sweetener made by NutraSweet that is between 7,000 and 13,000 times sweeter than sucrose (table sugar). In the European Union, it is known by the E number E961. It is moderately heat-stable, extremely potent, rapidly metabolized, completely eliminated, and does not appear to accumulate in the body.

The major metabolic pathway is hydrolysis of the methyl ester by esterases that are present throughout the body, which yields de-esterified neotame and methanol. Because only trace amounts of neotame are needed to sweeten foods, the amount of methanol derived from neotame is much lower than that found in common foods.

The product is attractive to food manufacturers, as its use greatly lowers the cost of production compared to using sugar or high fructose corn syrup (due to the lower quantities needed to achieve the same sweetening), while also benefitting the consumer by providing fewer "empty" sugar calories and a lower impact on blood sugar.

It is chemically similar to the artificial sweetener aspartame, but is used at vastly lower levels and is more stable. Chemically, it has a 3,3-dimethylbutyl group attached to the amino group of the aspartic acid portion of the molecule. Peptidases, which would typically break the peptide bond between the aspartic acid and phenylalanine moieties, are effectively blocked by the presence of the 3,3-dimethylbutyl moiety, thus reducing the production of phenylalanine during metabolism of the chemical. As a result, it is safe for consumption by those who suffer from phenylketonuria.