Neotame

Neotame
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
PubChem	9810996
UNII	VJ597D52EX Y
Jmol-3D images	Image 1
SMILES CC(C)(C)CCN[C@@H](CC(=O)O)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)OC
Properties
Molecular formula	C20H30N2O5
Molar mass	378.46 g mol−1
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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.^[1] It is moderately heat-stable, extremely potent, rapidly metabolized, completely eliminated and does not appear to accumulate in the body.^[2]

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, such as fruit and vegetable juices.[2] It has the characteristic aftertaste common to artificial sweeteners.

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),^[3] 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^{[citation needed]}. 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, thereby making its consumption by those who suffer from phenylketonuria safe.^[4] Neotame, simply a modified version of aspartame, contains all the same elements found in aspartame and more: the amino acids L-aspartic acid and L-phenylalanine, plus two organic groups, one known as a methyl ester group and the other as a neohexyl group. ^[5]

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.^[6]

Although over 100 corporate-sponsored studies were conducted on neotame to prove its safety prior to FDA approval,^[7] the controversy relating to a related sweetener, aspartame, has caused a stir among opponents of that additive. However, neotame and sucralose are the only two artificial sweeteners ranked as "safe" by the consumer advocacy group Center for Science in the Public Interest.^[8]

Consumer reports show that the taste of neotame, in comparison to natural sucrose, is extremely noticeable and is often described as bitter.

References

1. ^ New additives approved for use, Food Standards Agency, 26 November 2010
2. ^ Dr. Abbott, P.J. "Neotame", "International Programme on Chemical Safety". Accessed August 31, 2007.
3. ^ Food Navigator, Finance and Industry News. "Cost is the key to neotame's success". Accessed August 31, 2007.
4. ^ Science Toys, Ingredient Listings. "Neotame Ingredients". Accessed August 31, 2007.
5. ^ Dr. Janet Starr Hull. [1]
6. ^ International Life Sciences Institute, Summary of evaluations performed by JECFA. "JECFA Evaluations - Neotame". Accessed April 16, 2008.
7. ^ Neotame Science Brochure
8. ^ Comparison and Safety Ratings of Food Additives, Center for Science in the Public Interest

External links

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