Aspartame - From Wikipedia, the free encyclopedia

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Aspartame

http://en.wikipedia.org/wiki/Aspartame#Discovery_and_approval

From Wikipedia, the free encyclopedia

 

This sweetener is marketed under a number of trademark names, including Equal

, NutraSweet, 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 vitamin supplements and common in many sugar-free chewing gums.

However, aspartame is not always suitable for baking because it often breaks

down

when heated and loses much of its sweetness. In the European Union, it is also

known under the E number (additive code) E951. Aspartame is also one of the

sugar substitutes used by diabetics.

 

Aspartame is a subject of a public controversy due to perceived health risks

(see aspartame controversy). It has lost market share in recent years to

sucralose (Splenda, Altern, or E number E955).<SUP class=reference id=_ref-1>[2]

 

Chemistry

 

Aspartame is the methyl ester of the dipeptide of the natural amino acids L-

aspartic acid and L-phenylalanine. Under strongly acidic or alkaline

conditions, aspartame first generates methanol by hydrolysis. Under more severe

conditions, the peptide bonds are also hydrolyzed, resulting in the free amino

acids.

It is a nonpolar molecule.<SUP class=reference id=_ref-2>[3]

 

Properties and use

 

Aspartame is an attractive sweetener because it is 180 times sweeter than

sugar in typical concentrations, without the high energy value of sugar. While

aspartame, like other peptides, has a caloric value of 4 kilocalories (17

kilojoules) per 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 peptides, aspartame

may

hydrolyze (break down) into its constituent amino acids under conditions of

elevated temperature or high pH. This makes aspartame undesirable as a baking

sweetener, and prone to degradation in products hosting a high-pH, as required

for a long shelf life. The stability of aspartame under heating can be improved

to some extent by encasing it in fats or in maltodextrin. The stability when

dissolved in water depends markedly on pH. At room temperature, it is most

stable at pH 4.3, where its half-life is nearly 300 days. At pH 7, however, its

half-life is only a few days. Most soft-drinks have a pH between 3 and 5, where

aspartame is reasonably stable. In products that may require a longer shelf

life, such as syrups for fountain beverages, aspartame is sometimes blended with

a more stable sweetener, such as saccharin.[4]In products such as powdered

beverages, the amine in aspartame can undergo a Maillard reaction with the

aldehyde groups present in certain aroma compounds. The ensuing loss of both

flavor

and sweetness can be prevented by protecting the aldehyde as an acetal.

 

Discovery and approval

 

Aspartame was discovered in 1965 by James M. Schlatter, a chemist working for

G.D. Searle & Company. Schlatter had 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; as a

result, the U.S. Food and Drug Administration (FDA) did not approve its use as a

food additive in the United States for many years. In 1980, the FDA convened

a Public Board of Inquiry (PBOI) consisting of independent advisors charged

with examining the purported relationship between aspartame and brain cancer.

The PBOI concluded that aspartame does not cause brain damage, but it

recommended against approving aspartame at that time, citing unanswered

questions about

cancer in laboratory rats. At that point in time, there was no requirement in

place in FDA regulations to include brain research in the approval process,

only cancer research. In 1981, U.S. President Ronald 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, Hayes approved aspartame for use in

dry goods. http:.2F.2Farchive.gao.gov.2Fd28t5.2F133460.pdf_0 [6] 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.<

http:.2F.2Fwww.findarticles.com.2Fp.2Farticles.2Fmi_m0EUY.2Fis_22_6.2Fai_6292082\

1_0>[7] 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 unprofitableâ€.

<http:.2F.2Fwww.marketwire.com.2Fmw.2Frelease_html_b1.3Frelease_id.3D115447_0>

[8]

 

Metabolism

 

Upon ingestion, aspartame breaks down into several residual chemicals,

including aspartic acid, phenylalanine, methanol, and further breakdown products

including formaldehyde (when consumed by rats) [9] and 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 essential amino acid

phenylalanine is a health hazard to those born with 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.[10]

 

Health Concerns

 

Main article: Aspartame controversy

http://en.wikipedia.org/wiki/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.<SUP class=reference id=_ref-7>[11]<SUP class=reference

id=_ref-soffritti_0>[12]<SUP class=reference id=_ref-8>[13] 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.<SUP class=reference id=_ref-9>[14]<SUP class=reference id=_ref-10>

[15] The 2004 documentary Sweet Misery: A Poisoned World voices these same

concerns.

 

References

 

 

-- Merck Index, 11th Edition, 861.

-- John Schmeltzer. " Equal fights to get even as Splenda looks sweet] "

(subscription required), Chicago Tribune, 2 December 2004. Retrieved on

2007-07-04. 

 

^ 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. 

^ Fountain Beverages in the US. The Coca-Cola Company (May 2007).

^ How Products Are Made: Aspartame

^ http://archive.gao.gov/d28t5/133460.pdf

^ http://www.findarticles.com/p/articles/mi_m0EUY/is_22_6/ai_62920821

^ http://www.marketwire.com/mw/release html b1?release id=115447

^ 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. 

^ Aspartame - Labelling, UK Food Standards Agency, 18 July 2006.Retrieved on

2007-07-22.

^ 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.

^ 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. 

^ Roberts, H.J., " Does Aspartame Cause Human Brain Cancer, " Journal of

Advancement in Medicine, Volume 4(4):231-241, 1991.

^ 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

^ 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.102