Aspartame



Aspartame[1]
IUPAC name N-(L-α-Aspartyl)-L-phenylalanine,
1-methyl ester
Other names NutraSweet
Canderel
Equal
Identifiers
CAS number 22839-47-0
SMILES [NH3+] [C@@H](CC([O-])=O)C(N[C@@H]
(CC1=CC=CC=C1)C(OC)=O)=O
Properties
Molecular formula C14H18N2O5
Molar mass 294.301 g/mol
Melting point

246-247 °C

Boiling point

decomposes

Hazards
NFPA 704
1
1
0
 
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

Aspartame (or APM) (phenylalanine.

This sweetener is marketed under a number of trademark names, including Equal, NutraSweet, and Canderel, and is an ingredient of approximately 6,000 consumer foods and beverages sold worldwide. It is commonly used in diet soft drinks, and is often provided as a table condiment. It is also used in some brands of chewable diabetes.

Aspartame is a subject of public controversy due to possible health risks. See Aspartame controversy. It has lost market share in recent years to E number E955).[2]

Chemistry

Aspartame is the methyl peptide bonds are also hydrolyzed, resulting in the free amino acids. It is a nonpolar molecule.[3]

Properties and use

Aspartame is an attractive sweetener because it is 180 times as sweet as sugar in typical gram, the quantity of aspartame needed to produce a sweet taste is so small that its caloric contribution is negligible, which makes it a popular sweetener for those trying to avoid calories from sugar. The taste of aspartame is not identical to that of sugar: the sweetness of aspartame has a slower onset and longer duration than that of sugar, and some consumers find it unappealing. Blends of aspartame with acesulfame potassium — usually listed in ingredients as acesulfame K — are alleged to taste more like sugar, and to be sweeter than either substitute used alone.

Like many other saccharin.[4]

In products such as powdered beverages, the acetal.

Discovery and approval

Aspartame was discovered in 1965 by James M. Schlatter, a chemist working for synthesized aspartame in the course of producing an anti-ulcer drug candidate. He discovered its sweet taste serendipitously when he licked his finger, which had accidentally become contaminated with aspartame.[5]

Following initial safety testing, there was debate as to whether these tests had indicated that aspartame may cause cancer in rats[citation needed]; as a result, the Donald Rumsfeld, reapplied for FDA certification immediately after U.S. President Ronald Reagan took office.[6] In 1981, Reagan appointed Arthur Hull Hayes as FDA commissioner. Citing data from a Japanese study that had not been available to the members of the PBOI[citation needed], Hayes approved aspartame for use in dry goods.[7] In 1983 FDA further approved aspartame for use in carbonated beverages, and for use in other beverages, baked goods, and confections in 1993. In 1996, the FDA removed all restrictions from aspartame allowing it to be used in all foods.

In 1985, Monsanto bought G.D. Searle — and the aspartame business became a separate Monsanto subsidiary, the NutraSweet Company. On May 25 2000 Monsanto sold it to J.W. Childs Equity Partners II L.P.[8] The U.S. patent on aspartame expired in 1992. Since then the company has faced hot competition in market for aspartame from other manufacturers, including Ajinomoto, Merisant and the Holland Sweetener Company, which stopped making the chemical in late 2006 because "global aspartame markets are facing structural oversupply, which has caused worldwide strong price erosion over the last 5 years" making the business "persistently unprofitable”.[9]

Several European Union states approved aspartame in the 1980s, with EU-wide approval in 1994. The European Commission Scientific Committee on Food reviewed subsequent safety studies and reaffirmed the approval in 2002. The European Food Safety Authority reported in 2006 that the previously established Adequate Daily Intake was appropriate, after reviewing yet another set of studies.[10]

It has also been investigated and approved by the Joint Expert Committee on Food Additives of the United Nations Food and Agricultural Organization and World Health Organization.[11]

Metabolism

Upon ingestion, aspartame breaks down into several residual chemicals, including formic acid. There is some controversy surrounding the rate of breakdown into these various products and the effects that they have on those that consume aspartame-sweetened foods. (See Aspartame controversy)

The naturally-occurring phenylketonuria (PKU), a rare inherited disease that prevents phenylalanine from being properly metabolized. Since individuals with PKU must consider aspartame as an additional source of phenylalanine, foods containing aspartame sold in the United States must state "Phenylketonurics: Contains Phenylalanine" on their product labels.

In the UK, foods that contain aspartame must list the chemical among the product's ingredients and carry the warning 'Contains a source of phenylalanine' – this is usually at the foot of the list of ingredients. Manufacturers should print '"with sweetener(s)" on the label close to the main product name' on foods that contain 'sweeteners such as aspartame' or "with sugar and sweetener(s)" on 'foods that contain both sugar and sweetener'. 'This labelling is a legal requirement,'says the country's Food Standards Agency.[13]

Health Concerns

Main article: Aspartame controversy

Aspartame has been the subject of controversy regarding its safety and the circumstances of its approval by the American FDA and European FSA. Some studies have also recommended further investigation into possible connections between aspartame and negative effects such as headaches, brain tumors, brain lesions, and lymphoma.[14][15][16] These findings, combined with possible conflicts of interest involving CEO Donald Rumsfeld in the approval process, have engendered vocal activism regarding the possible risks of aspartame.[17][18]

References

  1. ^ Merck Index, 11th Edition, 861.
  2. ^ John Schmeltzer. "Equal fights to get even as Splenda looks sweet]" (subscription required), Chicago Tribune, 2 December 2004. Retrieved on 2007-07-04. 
  3. ^ David J. Ager, David P. Pantaleone, Scott A. Henderson, Alan R. Katritzky, Indra Prakash, D. Eric Walters (1998). "Commercial, Synthetic Nonnutritive Sweeteners". Angewandte Chemie International Edition 37 (13-24): 1802-1817. doi:10.1002/(SICI)1521-3773(19980803)37:13/14%3C1802::AID-ANIE1802%3E3.0.CO;2-9.
  4. ^ Fountain Beverages in the US. The Coca-Cola Company (May 2007).
  5. ^ How Products Are Made: Aspartame
  6. ^ Mieszkowski, Katharine (2007-10-08). Life will kill you: Can diet soda, cellphones and makeup give you cancer? The author of "The Secret History of the War on Cancer" discusses the health risks of, well, living.. Salon.
  7. ^ http://archive.gao.gov/d28t5/133460.pdf
  8. ^ http://www.findarticles.com/p/articles/mi_m0EUY/is_22_6/ai_62920821
  9. ^ http://www.marketwire.com/mw/release html b1?release id=115447
  10. ^ http://www.efsa.europa.eu/EFSA/efsa_locale-1178620753812_1178620765743.htm
  11. ^ http://www.dorway.com/offasprt.html
  12. ^ C. Trocho, R. Pardo, I. Rafecas, J. Virgili, X. Remesar, J. A. Fernandez-Lopez and M. Alemany (1998). "Formaldehyde derived from dietary aspartame binds to tissue components in vivo". Life Sciences 63 (5): 337-349. doi:10.1016/S0024-3205(98)00282-3.
  13. ^ Aspartame - Labelling, UK Food Standards Agency, 18 July 2006.Retrieved on 2007-07-22.
  14. ^ Olney, J.W., N.B. Farber, E. Spitznagel, L.N. Robins, 1996. "Increasing Brain Tumor Rates: Is There a Link to Aspartame?" Journal of Neuropathology and Experimental Neurology, Volume 55, pages 1115-1123.
  15. ^ Morando Soffritti, Fiorella Belpoggi, Davide Degli Esposti, Luca Lambertini, Eva Tibaldi, and Anna Rigano (2006). "First Experimental Demonstration of the Multipotential Carcinogenic Effects of Aspartame Administered in the Feed to Sprague-Dawley Rats" (reprint). Environmental Health Perspectives 114 (3): 379-385. doi:10.1289/ehp.8711.
  16. ^ Roberts, H.J., "Does Aspartame Cause Human Brain Cancer," Journal of Advancement in Medicine, Volume 4(4):231-241, 1991.
  17. ^ GAO 1986. "Six Former HHS Employees' Involvement in Aspartame's Approval," United States General Accounting Office, GAO/HRD-86-109BR, July 1986. http://archive.gao.gov/d4t4/130780.pdf
  18. ^ Gordon, Gregory, United Press International Investigation, "NutraSweet: Questions Swirl," 1987. http://www.dorway.com/upipaper.txt

Further reading

  • Morando Soffritti, Fiorella Belpoggi, Eva Tibaldi, Davide Degli Esposti, Michela Lauriola (13 June 2007). "Lifespan Exposure to Low Doses of Aspartame Beginning During Prenatal Life Increases Cancer Effects in Rats" (article in press). doi:10.1289/ehp.10271.
  • side effects of the Aspartame [1]
be-x-old:Аспартам
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Aspartame". A list of authors is available in Wikipedia.