Neotame

Neotame

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Ball-and-stick model of the neotame molecule
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
ChEBI	CHEBI:83503 N
ChemSpider	7986751 N
Jmol 3D model	Interactive image
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
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (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.

Chemistry

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.

Approval

Neotame was approved by the Food and Drug Administration (FDA) for general use in July 2002, and has now been approved by the EU to become a classified E number (E961), but it is not yet widely used in food products. Neotame also is approved for use in Australia and New Zealand. It is assigned the International Numbering System (INS) food additive code 961.

Although over 100 corporate-sponsored studies were conducted on neotame to prove its safety prior to FDA approval, the controversy relating to a related sweetener, aspartame, has caused a stir among opponents of that additive. However, neotame is the only artificial sweetener ranked as "safe" by the consumer advocacy group Center for Science in the Public Interest.

Patent

The patent covering the neotame molecule in the US, 5,480,668, was originally set to expire 7 November 2012, but was extended 973 days by the U.S. Patent and Trademark Office. The patent expired on 8 July 2015.

External links

• Official Neotame Website, Sweeteners Holdings, Inc.
• Neotame Artificial Sweetener Approved by FDA
• food.gov.uk