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Names

IUPAC name

Methyl L-α-aspartyl-L-phenylalaninate

Other names

N-(L-α-Aspartyl)-L-phenylalanine,

1-methyl ester

Identifiers

CASNumber

22839-47-0 (http://www.commonchemistry.org

/ChemicalDetail.aspx?ref=22839-47-0)

ChEBI CHEBI:2877 (https://www.ebi.ac.uk/chebi

/searchId.do?chebiId=2877)

ChEMBL ChEMBL171679 (https://www.ebi.ac.uk/chembldb

/index.php/compound/inspect/ChEMBL171679)

ChemSpider 118630 (http://www.chemspider.com/Chemical-

Structure.118630.html)

DrugBank DB00168 (http://www.drugbank.ca/drugs/DB00168)

Jmol 3D

model

Interactive image (http://chemapps.stolaf.edu

/jmol/jmol.php?model=O%3DC%28O%29C%5BC%40H

%5D%28N%29C%28%3DO%29N%5BC%40H

Aspartame[1]

AspartameFrom Wikipedia, the free encyclopedia

Aspartame (APM; /ˈæspərteɪm/ or /əˈspɑːrteɪm/) is anartificial, non-saccharide sweetener used as a sugarsubstitute in some foods and beverages. In the EuropeanUnion, it is codified as E951. Aspartame is a methyl ester ofthe aspartic acid/phenylalanine dipeptide. It was first soldunder the brand name NutraSweet. It was first synthesized in1965, and the patent expired in 1992.

The safety of aspartame has been the subject of severalpolitical and medical controversies, United States

congressional hearings and Internet hoaxes[3][4][5] since itsinitial approval for use in food products by the U.S. Food

and Drug Administration (FDA) in 1981.[6]:2 The EuropeanFood Safety Authority concluded in its 2013 re-evaluationthat aspartame and its breakdown products are safe for

human consumption at current levels of exposure,[7]

corroborating other medical reviews.[8] However, because itsbreakdown products include phenylalanine, aspartame mustbe avoided by people with the genetic conditionphenylketonuria (PKU).

Contents

1 Chemistry2 Mechanism of action3 Properties and use4 Discovery and approval5 Compendial status6 Safety and approval controversies7 Safety and health effects

7.1 Intake7.2 Metabolites

7.2.1 Aspartate7.2.2 Methanol7.2.3 Phenylalanine and

phenylketonuria7.3 Lactation7.4 Cancer7.5 Neurological and psychiatric symptoms

7.5.1 Headaches7.6 Weight change and hunger

8 Commercial uses8.1 NutraSweet Company8.2 Ajinomoto8.3 Holland Sweetener Company8.4 Competing products

9 Ant-killer hoax10 See also

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%5D%28C%28%3DO%29OC%29Cc1ccccc1)

KEGG C11045 (http://www.kegg.jp/entry/C11045)

UNII Z0H242BBR1 (http://fdasis.nlm.nih.gov

/srs/srsdirect.jsp?regno=Z0H242BBR1)

InChI=1S/C14H18N2O5/c1-21-14(20)11(7-9-5-3-2-4-6-9)16-13(19)10(15)8-12(17)18/h2-6,10-11H,7-8,15H2,1H3,(H,16,19)(H,17,18)/t10-,11-/m

0/s1

Key: IAOZJIPTCAWIRG-QWRGUYRKSA-N

InChI=1/C14H18N2O5/c1-21-14(20)11(7-9-5-3-2-4-6-9)16-13(19)10(15)8-12(17)18/h2-6,10-11H,7-8,15H2,1H3,(H,16,19)(H,17,18)/t10-,11-/m0/s1

Key: IAOZJIPTCAWIRG-QWRGUYRKBV

O=C(O)C[C@H](N)C(=O)N[C@H](C(=O)OC)Cc1ccccc1

Properties

Chemicalformula

C14H18N2O5

Molar mass 294.31 g·mol−1

Density 1.347 g/cm3

Melting

point

246 to 247 °C (475 to 477 °F; 519 to 520 K)

Boiling

point

decomposes

Solubilityin water

Sparingly soluble

Solubility Slightly soluble in ethanol

Acidity

(pKa)

4.5–6.0[2]

Hazards

NFPA 704

Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).

verify (what is ?)

Infobox references

11 References

Chemistry

Aspartame is a methyl ester of the dipeptide of the naturalamino acids L-aspartic acid and L-phenylalanine. Under

strongly acidic or alkaline conditions, aspartame maygenerate methanol by hydrolysis. Under more severeconditions, the peptide bonds are also hydrolyzed, resulting

in free amino acids.[9]

While known aspects of synthesis are covered by patents,

many details are proprietary.[10] Two approaches to synthesisare used commercially. In the chemical synthesis, the twocarboxyl groups of aspartic acid are joined into ananhydride, and the amino group is protected by converting itto a functional group that will not interfere in the nextreaction. Phenylalanine is converted to its methyl ester andcombined with the N-protected aspartic anhydride; then theprotecting group is removed from aspartic nitrogen by acidhydrolysis. The drawback of this technique is that abyproduct, the bitter-tasting β-form, is produced when thewrong carboxyl group from aspartic acid links tophenylalanine. A process using an enzyme from Bacillusthermoproteolyticus to catalyze the condensation of thechemically altered amino acids will produce high yieldswithout the β-form byproduct. A variant of this method,which has not been used commercially, uses unmodifiedaspartic acid, but produces low yields. Methods for directlyproducing aspartyl-phenylalanine by enzymatic means,followed by chemical methylation, have also been tried, but

not scaled for industrial production.[11]

Mechanism of action

The perceived sweetness of aspartame (and other sweetsubstances like acesulfame K) in humans is due to its bindingof the heterodimer G-protein coupled receptor formed by the

proteins TAS1R2 and TAS1R3.[12]

Properties and use

Aspartame is approximately 200 times sweeter than sucrose (table sugar). Due to this property, even though aspartameproduces four kilocalories of energy per gram (17 kJ/g) when metabolized, the quantity of aspartame needed to produce a

sweet taste is so small that its caloric contribution is negligible.[8] The taste of aspartame and other artificial sweeteners differsfrom that of table sugar in the times of onset and how long the sweetness lasts, though aspartame comes closest to sugar's taste

profile among approved artificial sweeteners.[10] The sweetness of aspartame lasts longer than that of sucrose, so it is often

blended with other artificial sweeteners such as acesulfame potassium to produce an overall taste more like sugar.[13]

Like many other peptides, aspartame may hydrolyze (break down) into its constituent amino acids under conditions ofelevated temperature or high pH. This makes aspartame undesirable as a baking sweetener, and prone to degradation in

InChI

SMILES

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Beta-aspartame differs from aspartame

based upon which carboxyl group of

aspartate binds to the nitrogen of

phenylalanine.

products hosting a high pH, as required for a long shelf life. The stability of aspartameunder 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, itshalf-life is only a few days. Most soft-drinks have a pH between 3 and 5, whereaspartame is reasonably stable. In products that may require a longer shelf life, such assyrups for fountain beverages, aspartame is sometimes blended with a more stable

sweetener, such as saccharin.[14]

Aspartame's major decomposition products are its cyclic dipeptide (in a2,5-diketopiperazine, or DKP, form), the de-esterified dipeptide (aspartyl-

phenylalanine), and its constituent components, phenylalanine,[15] aspartic acid,[16] and methanol.[17] At 180 °C, aspartame

undergoes decomposition to form a diketopiperazine derivative.[18]

In products such as powdered beverages, the amine in aspartame can undergo a Maillard reaction with the aldehyde groupspresent in certain aroma compounds. The ensuing loss of both flavor and sweetness can be prevented by protecting thealdehyde as an acetal.

Descriptive analyses of solutions containing aspartame report a sweet aftertaste as well as bitter and off-flavor aftertastes.[19]

Discovery and approval

Aspartame was discovered in 1965 by James M. Schlatter, a chemist working for G.D. Searle & Company. Schlatter hadsynthesized aspartame as an intermediate step in generating a tetrapeptide of the hormone gastrin, for use in assessing an

anti-ulcer drug candidate.[20] He accidentally discovered its sweet taste when he licked his finger, which had become

contaminated with aspartame, to lift up a piece of paper.[8][21][22]

In 1975, prompted by issues regarding Flagyl and Aldactone, a U.S. FDA task force team reviewed 25 studies submitted by

the manufacturer, including 11 on aspartame. The team reported "serious deficiencies in Searle's operations and practices".[6]

The FDA sought to authenticate 15 of the submitted studies against the supporting data. In 1979, the Center for Food Safetyand Applied Nutrition (CFSAN) concluded, since many problems with the aspartame studies were minor and did not affect the

conclusions, the studies could be used to assess aspartame's safety.[6]

In 1980, the FDA convened a Public Board of Inquiry (PBOI) consisting of independent advisors charged with examining thepurported relationship between aspartame and brain cancer. The PBOI concluded aspartame does not cause brain damage, butit recommended against approving aspartame at that time, citing unanswered questions about cancer in laboratory

rats.[6]:94–96[23]

Citing data from a Japanese study that had not been available to the members of the PBOI,[24] and after seeking advice from

an expert panel that found fault with statistical analyses underlying the PBOI's hesitation, yet argued against approval,[6]:53

FDA commissioner Hayes approved aspartame for use in dry goods.[6] In 1983, the FDA further approved aspartame for usein carbonated beverages, and for use in other beverages, baked goods, and confections in 1993. In 1996, the FDA removed allrestrictions from aspartame, allowing it to be used in all foods.

Several European Union countries approved aspartame in the 1980s, with EU-wide approval in 1994. The EuropeanCommission Scientific Committee on Food reviewed subsequent safety studies and reaffirmed the approval in 2002. TheEuropean Food Safety Authority reported in 2006 that the previously established Acceptable daily intake was appropriate,

after reviewing yet another set of studies.[25]

Compendial status

British Pharmacopoeia[26]

United States Pharmacopeia[27]

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Safety and approval controversies

Aspartame has been found to be safe for human consumption by more than ninety countries worldwide,[28][29] with FDAofficials describing aspartame as "one of the most thoroughly tested and studied food additives the agency has ever approved"

and its safety as "clear cut",[30] but has been the subject of several controversies, hoaxes[3] and health scares.[31]

Initially aspartame was approved by the U.S. Food and Drug Administration (FDA) in 1974; however, problems with Searle'ssafety testing program, including testing of aspartame, were discovered subsequently. The approval was rescinded thefollowing year, but after outside reviews of the problematic tests and additional testing, final approval was granted in 1981.

Because allegations of conflicts of interest marred the FDA's approval of aspartame,[6][30][32] the U.S. GovernmentAccountability Office reviewed the actions of involved officials in 1986 and the approval process in 1987; neither the

allegations of conflict of interest nor problems in the final approval process were substantiated.[6][33]

In addition, the Centers for Disease Control investigated in 1984 and was unable to find any significant epidemiological

associations to serious risk or harm.[34]

Since December 1998, a widely circulated email hoax cited aspartame as the cause of numerous diseases.[35]

The weight of existing scientific evidence indicates that aspartame is safe at current levels of consumption as a non-nutritive

sweetener.[8] Reviews conducted by regulatory agencies decades after aspartame was first approved have supported its

continued availability.[36]

Safety and health effects

The safety of aspartame has been studied extensively since its discovery with research that includes animal studies, clinical

and epidemiological research, and postmarketing surveillance.[37] Aspartame is one of the most rigorously tested food

ingredients.[38] Peer-reviewed comprehensive review articles and independent reviews by governmental regulatory bodieshave analyzed the published research on the safety of aspartame and have found aspartame is safe for consumption at current

levels.[8][37][39][40] Aspartame has been deemed safe for human consumption by over 100 regulatory agencies in their

respective countries,[40] including the UK Food Standards Agency,[41] the European Food Safety Authority (EFSA)[42] and

Health Canada.[43]

Intake

The acceptable daily intake (ADI) value for aspartame, as well as other food additives studied, is defined as the "amount of a

food additive, expressed on a body weight basis, that can be ingested daily over a lifetime without appreciable health risk."[44]

The Joint FAO/WHO Expert Committee on Food Additives (JECFA) and the European Commission's Scientific Committee on

Food has determined this value is 40 mg/kg of body weight for aspartame,[45] while FDA has set its ADI for aspartame at

50 mg/kg.[46]

The primary source for exposure to aspartame in the United States is diet soft drinks, though it can be consumed in other

products, such as pharmaceutical preparations, fruit drinks, and chewing gum among others in smaller quantities.[8] A 12 USfluid ounce (355 ml) can of diet soda contains 180 milligrams (0.0063 oz) of aspartame, and for a 75 kg (165 lb) adult, it takesapproximately 21 cans of diet soda daily to consume the 3,750 milligrams (0.132 oz) of aspartame that would surpass the

FDA's 50 milligrams per kilogram of body weight ADI of aspartame from diet soda alone.[46]

Reviews have analyzed studies which have looked at the consumption of aspartame in countries worldwide, including theUnited States, countries in Europe, and Australia, among others. These reviews have found that even the high levels of intakeof aspartame, studied across multiple countries and different methods of measuring aspartame consumption, are well below

the ADI for safe consumption of aspartame.[8][37][40][45] Reviews have also found that populations that are believed to beespecially high consumers of aspartame such as children and diabetics are below the ADI for safe consumption, even

considering extreme worst-case scenario calculations of consumption.[8][37]

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In a report released on 10 December 2013, the EFSA said that, after an extensive examination of evidence, it ruled out the"potential risk of aspartame causing damage to genes and inducing cancer," and deemed the amount found in diet sodas an

amount safe to consume.[47]

Metabolites

Aspartame is rapidly hydrolyzed in the small intestines. Even with ingestion of very high doses of aspartame (over

200 mg/kg), no aspartame is found in the blood due to the rapid breakdown.[8] These metabolites have been studied in a widerange of populations including infants, children, adolescents, and healthy adults. In healthy adults and children, evenenormous doses of aspartame do not lead to plasma levels of metabolites that are a concern for safety.

Upon ingestion, aspartame breaks down into residual components, including aspartic acid, phenylalanine, methanol,[48] in ratio

of 4:5:1 by mass[49] and further breakdown products including formaldehyde[50] and formic acid, accumulation of the latterbeing suspected as the major cause of injury in methanol poisoning. Human studies show that formic acid is excreted fasterthan it is formed after ingestion of aspartame. In some fruit juices, higher concentrations of methanol can be found than the

amount produced from aspartame in beverages.[16]

Aspartate

Aspartic acid (aspartate) is one of the most common amino acids in the typical diet. As with methanol and phenylalanine,intake of aspartic acid from aspartame is less than would be expected from other dietary sources. At the 90th percentile ofintake, aspartame provides only between 1% and 2% of the daily intake of aspartic acid. There has been some

speculation[51][52] that aspartame, in conjunction with other amino acids like glutamate, may lead to excitotoxicity, inflicting

damage on brain and nerve cells. However, clinical studies have shown no signs of neurotoxic effects,[8] and studies ofmetabolism suggest it is not possible to ingest enough aspartic acid and glutamate through food and drink to levels that would

be expected to be toxic.[40]

Methanol

The methanol produced by the metabolism of aspartame is absorbed and quickly converted into formaldehyde and thencompletely oxidized to formic acid, which, due to its long half life, is considered the primary mechanism of toxicity inmethanol poisoning. The methanol from aspartame is unlikely to be a safety concern for several reasons. The amount ofmethanol in aspartame is less than that found in fruit juices and citrus fruits, and there are other dietary sources for methanolsuch as fermented beverages. Therefore, the amount of methanol produced from aspartame is likely to be less than that fromnatural sources. With regard to formaldehyde, it is rapidly converted in the body, and the amounts of formaldehyde from themetabolism of aspartame are trivial when compared to the amounts produced routinely by the human body and from otherfoods and drugs. At the highest expected human doses of consumption of aspartame, there are no increased blood levels of

methanol or formic acid,[8] and ingesting aspartame at the 90th percentile of intake would produce 25 times less methanol

than what would be considered toxic.[40]

Phenylalanine and phenylketonuria

High levels of the naturally-occurring essential amino acid phenylalanine are a health hazard to those born withphenylketonuria (PKU), a rare inherited disease that prevents phenylalanine from being properly metabolized. Sinceindividuals 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.[53]

In the UK, foods that contain aspartame are legally required by the country's Food Standards Agency to list the substanceamong the product's ingredients and carry the warning "Contains a source of phenylalanine" – this is usually at the foot of thelist of ingredients. Manufacturers are also required to print '"with sweetener(s)" on the label close to the main product nameon foods that contain "sweeteners such as aspartame" or "with sugar and sweetener(s)" on "foods that contain both sugar and

sweetener".[54]

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In Canada, foods that contain aspartame are legally required by the country to list the substance among the product'singredients and include a measure of the amount of aspartame per serving. As well, labels must state that the product contains

phenylalanine – this is usually in the order of ingredients, contained in brackets.[55]

Phenylalanine is one of the essential amino acids and is required for normal growth and maintenance of life. Concerns aboutthe safety of phenylalanine from aspartame center largely on hypothetical changes in neurotransmitter levels as well as ratiosof neurotransmitters to each other in the blood and brain that could lead to neurological symptoms. Reviews of the literature

have found no consistent findings to support such concerns,[40] and while high doses of aspartame consumption may havesome biochemical effects, these effects are not seen in toxicity studies to suggest aspartame can adversely affect neuronal

function.[8] Like methanol, the typical diet will lead to ingestion of significantly higher amounts of phenylalanine than would

be expected from aspartame consumption.[40] People with the genetic disorder phenylketonuria are advised to avoidaspartame as they have a decreased ability to metabolize phenylalanine. Common foods such as milk, meat, and fruits provide

far greater amounts of these metabolites in a diet than does aspartame.[40]

Lactation

In a study done in 1979, the effect of aspartame ingestion on blood and milk amino acid levels in lactating women was

tested.[56] In this study, six women from the ages of 20 to 29 with established lactation were studied after oral administrationof aspartame or lactose (50 mg/kg body weight) in a random order, with the intent to study the differences in breast milkbetween the two. The study resulted with the conclusion that aspartame administration at 50 mg/kg body weight has a smalleffect upon the milk aspartate levels and although a small increase in aspartate time-effect scores was noted over the

four-hour postabsorptive period, no significant difference was noted over the entire 24-hour watching period.[56]

Cancer

Reviews have found no association between aspartame and cancer. These reviews have looked at numerous carcinogenicitystudies in animals, epidemiologic studies in humans, as well as in vitro genotoxicity studies. These studies have found nosignificant evidence that aspartame causes cancer in animals, damages the genome, or causes cancer in humans at doses

currently used.[8][37][40][57] This position is supported by multiple regulatory agencies like the FDA[58] and EFSA as well as

scientific bodies such as the National Cancer Institute.[46] Aspartame did not show any DNA-damaging properties either.[59]

Concern about possible carcinogenic properties of aspartame was originally raised and popularized in the mainstream mediaby John Olney in the 1970s and again in 1996 by suggesting that aspartame may be related to brain tumors. Reviews have

found that these concerns were flawed, due to reliance on the ecological fallacy[59] and the purported mechanism of causingtumors being unlikely to actually cause cancer. Independent agencies such as the FDA and National Cancer Institute have

reanalyzed multiple studies based on these worries and found no association between aspartame and brain cancer.[40]

As discussed in the article on controversies around aspartame, the Cesare Maltoni Cancer Research Center of the EuropeanRamazzini Foundation of Oncology and Environmental Sciences released several studies which claimed that aspartame can

increase several malignancies in rodents, concluding that aspartame is a potential carcinogen at normal dietary doses.[60][61]

The EFSA[62] and the FDA[58] discounted the study results due to lack of transparency and numerous flaws in the study,finding no reason to revise their previously established acceptable daily intake levels for aspartame.

Neurological and psychiatric symptoms

Numerous allegations have been made via the Internet and in consumer magazines purporting neurotoxic effects of aspartame

leading to neurological or psychiatric symptoms such as seizures, headaches, and mood changes.[8] Review of the

biochemistry of aspartame has found no evidence that the doses consumed would plausibly lead to neurotoxic effects.[63]

Comprehensive reviews have not found any evidence for aspartame as a cause for these symptoms.[8][37][40] One review did

provide a theoretical biochemical background of neurotoxicity and suggested further testing.[64] However, a panel of EFSAexperts noted that this review's conclusions were partially based on Internet sources and therefore were not scientificallyrobust. These experts also concurred with a critique that significant scientific errors were made in the critical review that led

to unsubstantiated and misleading interpretations.[37] A review of the pediatric literature did not show any significant findings

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for safety concerns with regard to neuropsychiatric conditions such as panic attacks, mood changes, hallucinations or with

ADHD or seizures.[65]

Headaches

Headaches are the most common symptom reported by consumers.[8] While one small review noted aspartame is likely one ofmany dietary triggers of migraines, in a list that includes "cheese, chocolate, citrus fruits, hot dogs, monosodium glutamate,

aspartame, fatty foods, ice cream, caffeine withdrawal, and alcoholic drinks, especially red wine and beer,"[66] other reviews

have noted conflicting studies about headaches[8][67] and still more reviews lack any evidence and references to support this

claim.[37][40][65]

Weight change and hunger

Since the caloric contribution of aspartame is negligible, it has been used as a means for weight loss through its role as a sugarsubstitute, with reviews finding that aspartame may aid in weight loss as part of a multidisciplinary weight loss program. On its

own, aspartame is not known by medical literature to cause weight gain or weight loss.[8][40] Although some researchers have

stated that aspartame contributes to weight gain, hunger and increase in appetite,[8][68] broad reviews and regulators conclude

that aspartame has no appreciable effect on appetite.[8][37] Another systematic review concluded that there is a correlationbetween consumption of artificially sweetened beverages and weight gain in children, but that no clear causal link has been

determined. [69]

Commercial uses

Under the trade names Equal, NutraSweet, and Canderel, aspartame is an ingredient in approximately 6,000 consumer foodsand beverages sold worldwide, including (but not limited to) diet sodas and other soft drinks, instant breakfasts, breath mints,cereals, sugar-free chewing gum, cocoa mixes, frozen desserts, gelatin desserts, juices, laxatives, chewable vitaminsupplements, milk drinks, pharmaceutical drugs and supplements, shake mixes, tabletop sweeteners, teas, instant coffees,topping mixes, wine coolers and yogurt. It is provided as a table condiment in some countries. Aspartame is less suitable forbaking than other sweeteners, because it breaks down when heated and loses much of its sweetness.

NutraSweet Company

In 1985, Monsanto Company bought G.D. Searle, and the aspartame business became a separate Monsanto subsidiary, the

NutraSweet Company. In March 2000, Monsanto sold it to J.W. Childs Equity Partners II L.P.[70] European use patents on

aspartame expired starting in 1987,[71] and the U.S. patent expired in 1992. Since then, the company has competed for marketshare with other manufacturers, including Ajinomoto, Merisant and the Holland Sweetener Company.

Ajinomoto

Many aspects of industrial synthesis of aspartame were established by Ajinomoto.[10] In 2004, the market for aspartame, inwhich Ajinomoto, the world's largest aspartame manufacturer, had a 40 percent share, was 14,000 metric tons a year, and

consumption of the product was rising by 2 percent a year.[72] Ajinomoto acquired its aspartame business in 2000 from

Monsanto for $67M.[73]

In 2008, Ajinomoto sued British supermarket chain Asda, part of Wal-Mart, for a malicious falsehood action concerning its

aspartame product when the substance was listed as excluded from the chain's product line, along with other "nasties".[74] In

July 2009, a British court found in favour of Asda.[75] In June 2010, an appeals court reversed the decision, allowing

Ajinomoto to pursue a case against Asda to protect aspartame's reputation.[76] Asda said that it would continue to use the term

"no nasties" on its own-label products,[77] but the suit was settled in 2011 with Asda choosing to remove references to

aspartame from its packaging.[78]

In November 2009, Ajinomoto announced a new brand name for its aspartame sweetener – AminoSweet.[79]

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Holland Sweetener Company

A joint venture of DSM and Tosoh, the Holland Sweetener Company manufactured aspartame using the enzymatic process

developed by Toyo Soda (Tosoh) and sold as the brand Sanecta.[80] Additionally, they developed a combination aspartame-

acesulfame salt under the brand name Twinsweet.[81] They left the sweetener industry in late 2006, because "global aspartamemarkets are facing structural oversupply, which has caused worldwide strong price erosion over the last five years", making

the business "persistently unprofitable".[82]

Competing products

Because sucralose, unlike aspartame, retains its sweetness after being heated, and has at least twice the shelf life of

aspartame, it has become more popular as an ingredient.[83] This, along with differences in marketing and changing consumer

preferences, caused aspartame to lose market share to sucralose.[84][85] In 2004, aspartame traded at about $30/kg and

sucralose, which is roughly three times sweeter by weight, at around $300/kg.[86]

Ant-killer hoax

Aspartame has been falsely claimed to have been originally developed as ant poison. The source for this was a satirical article

posted on "thespoof" website.[87][88] Further claims that the substance actually is poisonous to ants were inferred from thatonline article being quoted as fact by various anti-aspartame websites, and videos of numerous trials of this rumor have beenshown on YouTube, or posted on social networks, some even claiming success in eradicating ants with Aspartame or with

other sweeteners.[87]

See also

Aspartame controversyNutraSweetSteviaPhenylalanine ammonia lyase

References

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Magnuson BA; Burdock GA; Doull J; et al. (2007). "Aspartame: a safety evaluation based on current use levels, regulations, andtoxicological and epidemiological studies". Critical Reviews in Toxicology. 37 (8): 629–727. doi:10.1080/10408440701516184.PMID 17828671.

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David J. Ager, David P. Pantaleone, Scott A. Henderson, Alan R. Katritzky, Indra Prakash, D. Eric Walters (1998). "Commercial,Synthetic Non-nutritive Sweeteners". Angewandte Chemie International Edition. 37 (13–24): 1802–1817.doi:10.1002/(SICI)1521-3773(19980803)37:13/14<1802::AID-ANIE1802>3.0.CO;2-9.

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O'Donnell, Kay (2006). "6 Aspartame and Neotame". In Mitchell, Helen Lucy. Sweeteners and sugar alternatives in foodtechnology. Blackwell. pp. 86–95. ISBN 1-4051-3434-8. Retrieved 26 July 2011.

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Yagasaki, Makoto; Hashimoto, Shin-ichi (November 2008). "Synthesis and application of dipeptides; current status andperspectives". Applied Microbiology and Biotechnology. 81 (1): 13–22. doi:10.1007/s00253-008-1590-3. PMID 18795289.

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