aspartame

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For more information on aspartame, visit Britannica.com.

Background

Aspartame is an artificial sweetener used in reduced calorie foods. It is derived primarily from two naturally occurring amino acids chemically combined and designated by the chemical name N-L-aaspartyl-L-phenylalanine-l-methyl ester (APM). Discovered inadvertently in 1965, it was later patented and is currently the most utilized artificial sweetener in the United States.

Aspartame is a white, odorless, crystalline powder. It is about 200 times sweeter than sugar and is readily dissolvable in water. It has a sweet taste without the bitter chemical or metallic aftertaste reported in other artificial sweeteners. These properties make it a good ingredient to use as a sugar replacement in many food recipes. However, aspartame does tend to interact with other food flavors, so it cannot perfectly replace sugar. Recipes for baked goods, candies, and other products must be modified if aspartame is utilized. Although aspartame can be used in microwave recipes, it is sensitive to extensive heating, which makes it unsuitable for baking.

The fact that aspartame provides sweetness and flavor without imparting other physical characteristics such as bulk or calories like other sweeteners makes it unique. Another useful trait is that it has a synergistic effect with other sweeteners, making it possible to use less total sweetener. In addition to sweetening foods, aspartame is used to reduce calories, and intensify and extend fruit flavors.

History

Humans have desired foods with a sweet taste for thousands of years. Ancient cave paintings at Arana in Spain show a neolithic man taking honey from a wild bee's nest. It has been suggested that early humans might have used the sweet taste of foods to tell them which ones would be safe to eat. It is even thought that the desire for sweet taste might be an innate human trait. Unfortunately, many of the foods that are naturally sweet contain relatively large amounts of calories and carbohydrates.

Alternative sweeteners were developed to provide the sweet taste without the unnecessary calories. They also provide the additional benefits of enhancing the palatability of pharmaceuticals, aiding in the management of diabetes, and providing a cost-effective source where sugar is not available. The first one, saccharin, was discovered in 1879 and has been used in products such as toothpaste, mouthwash, and sugarless gum.

The sugarlike taste of aspartame was discovered accidentally by James Schlatter, an American drug researcher at G.D. Searle and Co. in 1965. While working on an antiulcer drug, he inadvertently spilled some APM on his hand. Figuring that the material was not toxic, he went about his work without washing it off. He discovered APM's sweet taste when he licked his finger to pick up a piece of weighing paper. This initial breakthrough then led the company to screen hundreds of modified versions of APM. However, none of these materials offered all of the advantages found in the original compound, including economical manufacturing, excellent taste quality and potency, natural metabolic pathways for digestion, excellent stability, and very low toxicity. Consequently, the company pursued and was granted United States patent 3,492,131 and various international patents, and the initial discovery was commercialized. The U.S. patent expired in 1992, and the technology is now available to any company who wants to use it.

After many years of toxicity testing, the FDA initially approved aspartame's use as a sweetener in 1980. However, a hallmark of synthetic chemicals used in food products is that their safety is under constant scrutiny. Aspartame is no exception and has been surrounded by some controversy concerning its safety since its introduction. Most of these concerns were put to rest in late 1984, when after investigating various aspartame-related complaints, the FDA and the Centers for Disease Control concluded that the substance is safe and does not represent a widespread health risk. This conclusion was further supported by the American Medical Association in 1985, and aspartame has been gaining market share ever since. In addition to its use in the United States, aspartame has also been approved for use in over 93 foreign countries.

Aspartame has been marketed since 1983 by Searle under the brand names NutraSweet' and Equal'. Currently, NutraSweet' is a very popular ingredient and is used in more than 4,000 products, including chewing gum, yogurt, diet soft drinks, fruit-juices, puddings, cereals, and powdered beverage mixes. In the U.S. alone, NutraSweet®'s sales topped $705 million in 1993, according to the company.

Raw Materials

Aspartame is primarily derived from compounds called amino acids. These are chemicals which are used by plants and animals to create proteins that are essential for life. Of the 20 naturally occurring amino acids, two of them, aspartic acid and phenylalanine, are used in the manufacture of aspartame.

All amino acids molecules have some common characteristics. They are composed of an amino group, a carboxyl group, and a side chain. The chemical nature of the side chain is what differentiates the various amino acids. Another characteristic of amino acids is the ability to form different molecular configurations known as isomers. These isomers are designated by the letters L and D. Aspartame is composed of only L, L isomers; none of the other isomer combinations taste sweet. The sweet taste of aspartame could not have been predicted by looking at the two amino acids that it is derived from. L-aspartic acid has a flat taste and L-phenylalanine tastes bitter. However, when the two compounds are chemically combined and the L-phenylalanine is slightly modified, a sweet taste is achieved.

Aspartic acid is one of five amino acids that have a "charged" side group. The charged side group on aspartic acid is (-CH₂-COOH). When put in water, this material ionizes and becomes negatively charged. Phenylalanine has a nonpolar, hydrophobic side group which is not compatible with water. It is made up of a six carbon ring and is attached to the main amino acid backbone via a methyl (-CH₂) group. Prior to synthesis into aspartame, it is reacted with methanol. This adds a methyl group which is linked to the molecule by an oxygen, and the compound is converted to a methyl ester. The methanol required for the synthesis of aspartame has the chemical structure (CH₃-OH). This is a very common material and is used extensively by organic chemists for various chemical syntheses.

The Manufacturing
Process

Although its components—aspartic acid, phenylalanine, and methanol—occur naturally in foods, aspartame itself does not and must be manufactured. NutraSweet' (aspartame) is made through fermentation and synthesis processes.

Fermentation

Direct fermentation produces the starting amino acids needed for the manufacture of aspartame. In this process, specific types of bacteria which have the ability to produce certain amino acids are raised in large quantities. Over the course of about three days, the amino acids are harvested and the bacteria are destroyed.

• To start the fermentation process, a sample from a pure culture of bacteria is put into a test tube containing the nutrients necessary for its growth. After this initial inoculation the bacteria begin to multiply. When their population is large enough, they are transferred to a seed tank. The bacterial strains used to make L-aspartic acid and L-phenylalanine are B. flavum and C. glutamicum respectively.
• The seed tank provides an ideal environment for growing more bacteria. It is filled with the things bacteria need to thrive, including warm water and carbohydrate foods like cane molasses, glucose, or sucrose. It also has carbon sources like acetic acid, alcohols or hydrocarbons, and nitrogen sources such as liquid ammonia or urea. These are required for the bacteria to synthesize large quantities of the desired amino acid. Other growth factors such as vitamins, amino acids, and minor nutrients round out seed tank contents. The seed tank is equipped with a mixer, which keeps the growth medium moving, and a pump, which delivers filtered, compressed air. When enough bacterial growth is present, the contents from the seed tank are pumped to the fermentation tank.
• The fermentation tank is essentially a larger version of the seed tank. It is filled with the same growth media found in the seed tank and also provides a perfect environment for bacterial growth. Here the bacteria are allowed to grow and produce large quantities of amino acids. Since pH control is vital for optimal growth, ammonia water is added to the tank as necessary.
• When enough amino acid is present, the contents of the fermentation tank are transferred out so isolation can begin. This process starts with a centrifugal separator, which isolates a large portion of the bacterial amino acids. The desired amino acid is further segregated and purified in an ion-exchange column. From this column, the amino acids are pumped to a crystallizing tank and then to a crystal separator. They are then dried and readied for the synthesis phase of aspartame production.

Synthesis

Aspartame can be made by various synthetic chemical pathways. In general, phenylalanine is modified by a reaction with methanol and then combined with a slightly modified aspartic acid which eventually forms aspartame.

• The amino acids derived from the fermentation process are initially modified to produce aspartame. Phenylalanine is reacted with methanol resulting in a compound called L-phenylalanine methyl ester. Aspartic acid is also modified in such a way to shield various portions of the molecule from the effects of further reactions. One method is by reacting the aspartic acid with substances that result in added benzyl rings to protect these sites. This ensures that further chemical reactions will occur only on specific parts of the aspartic acid molecule.
• After the amino acids are appropriately modified, they are pumped into a reactor tank, where they are allowed to mix at room temperature for 24 hours. The temperature is then increased to approximately 149°F (65 °C) and maintained for another 24 hours. The reaction is then cooled to room temperature. It is diluted with an appropriate solvent and cooled to about 0°F (-18°C), causing crystallization. The crystals are then isolated by filtration and dried. These crystals are an intermediate of aspartame which must be further modified.
• The intermediate is converted to aspartame by reacting it with acetic acid. This reaction is performed in a large tank filled with an aqueous acid solution, a palladium metal catalyst, and hydrogen. It is thoroughly mixed and allowed to react for about 12 hours.

Purification

• The metal catalyst is removed by filtration, and the solvent is distilled, leaving a solid residue. This residue is purified by dissolving it in an aqueous ethanol solution and recrystallizing. These crystals are filtered and dried to provide the finished, powder aspartame.

Quality Control

The quality of the compounds is checked regularly during the manufacturing process. Of particular importance are frequent checks of the bacterial culture during fermentation. Also, various physical and chemical properties of the finished product are checked, such as pH level, melting point, and moisture content.

The Future

Currently, there are only three alternative sweeteners in the United States that can be used in food products. While aspartame is perhaps one of the best available, scientists are looking for new ways to make these sweeteners taste as much like sugar as possible. Their research has been focused in three areas, including finding new derivatives, blending sweeteners, and enhancing the efficiency of aspartame.

Most of the chemical derivative work has centered on finding compounds which will fit into the taste bud receptors better than traditional aspartame. Using aspartame as the model, researchers believe they will be able to improve various characteristics by making slight modifications. For example, they have found that when L-aspartic acid alone is modified in a certain way, it gives products that have a sweet taste. Future research will likely focus on these kinds of derivatives.

Another area of research focuses on improving the heat stability of aspartame. Using encapsulation technology, aspartame has been developed which can be used in baked goods and baking mixes. Initial test results are positive, and FDA approval has been granted for bakery applications.

Since only three synthetic sugar substitutes are currently approved for use in food in the U.S., combining artificial sweeteners in products is becoming an important technological advance. Here, scientists combine two or three sweeteners in an effort to make the product taste more sugarlike.

Where to Learn More

Books

Nabors, Lyn, and Robert Gelardi. Alternative Sweeteners. Marcel Dekker, Inc., 1986.

Periodicals

Best, Daniel and Lisa Nelson. "Low-calorie foods and sweeteners." Prepared Foods, June 1993, p. 47.

Tomasula, Dean. "Sweet as sugar: artificial sweetener producers are blending products, in search of a market winning combination." Chemical Marketing Reporter, June 27, 1994, p. S22.

[Article by: Perry Romanowski]

A white, crystalline compound, 1-aspartyl-1-phenylalanine methyl ester (APM), with formula (1). It is slightly

The sweetness of aspartame relative to sucrose is a function of the latter's concentration, and is also dependent upon the presence of other flavors and materials. In a number of applications, such as chewing gum and various fruit-flavored products, aspartame favorably extends and enhances the flavor perception, and it shows synergy with other sweeteners. The sweetness perception may also last longer with aspartame than with sucrose or other sweeteners. See also Sucrose.

Aspartame is metabolized to its component amino acids, which are further metabolized by the usual metabolic pathways. Under certain conditions of heat and pH in aqueous solution, aspartame is transformed into its diketopiperazine derivative, 3,6-dioxo-5-benzyl-2-piperazineacetic acid (2), which is tasteless.

This property limits the use of aspartame when it is exposed to high temperatures, such as in baking. The stability of aspartame in aqueous solution is pH-dependent; it is most stable at a pH of approximately 4. The rate of conversion (its half-life is 262 days at 77°F or 25°C) is sufficiently slow under the conditions of normal use that aspartame has found an increasing number of applications in various food products, and is particularly successful in soft drinks. The safety of aspartame has been established by studies in animals and human beings. Aspartame has been approved in many countries for uses in both dry and wet applications.

An artificial sweetener, aspartyl-phenylalanine methyl ester, some 200 times as sweet as sucrose. Stable for a limited time (a few months) in solution, when it gradually breaks down. Used in soft drinks, dessert mixes, and as a ‘table top sweetener’. The major trade names are Canderel, Equal, Nutrasweet, and Sanecta.

Because aspartame contains phenylalanine, it is specifically recommended that children with phenylketonuria avoid consuming it, although the amounts that would normally be consumed are small.

An artificial sweetener 200 times sweeter than sugar. It contains virtually no calories and, unlike some other sweeteners, has no bitter after-taste. It is made of two amino acids, aspartic acid and phenylalanine. It is the most widely used intense sweetener, but it cannot be used in cooking. It quickly loses its sweetness in hot water but is stable for 2-3 months in cold soft drinks. The Food and Drug Administration in the USA says it is safe for a healthy 150-pound adult to consume up to 3.5 grams of aspartame per day. In the UK, the acceptable daily intake is 40 mg per kg body weight (i.e. 2.8 g for a 70 kg adult). There is some doubt about the safety of consuming larger amounts of aspartame. Some people who habitually use the sweetener have reported migraines and headaches, and a few have suffered swelling of the larynx. In addition, it is believed that aspartame may have a toxic effect on the foetal brain. Therefore some people think its use should be avoided by pregnant and lactating women, and young children. People suffering from phenylketonuria (an inborn defect of protein metabolism) are sensitive to phenylalanine, and are generally advised to avoid aspartame.

[ah-SPAHR-taym; AS-pahr-taym] An artificial sweetener that's 180-200 times sweeter than sugar. It's synthesized from two amino acids (aspartic acid and phenylalanine), the building blocks of protein, and contains about 4 calories per gram. Regular aspartame breaks down and loses its sweetness when heated but is excellent for sweetening cold dishes. A new encapsulated (and therefore heat-stable) form of this sweetener has been developed especially for baking. At this writing, however, it's not available to consumers. See also acesulfame-k; alitame; saccharin; sucralose.

A synthetic compound of two amino acids (l-aspartyl-l-phenylalanine o-methyl ester) used as sweetener in low-calorie drinks. It is 180 times as sweet as sucrose (table sugar); the amount equal in sweetness to a teaspoon of sugar contains 0.1 calorie.

A lowcalorie sweetening agent about 200 times as sweet as sucrose.

Aspartame[1]
IUPAC name N-(L-α-Aspartyl)-L-phenylalanine, 1-methyl ester
Identifiers
CAS number	22839-47-0 Y
ChemSpider	118630 Y
UNII	Z0H242BBR1 Y
DrugBank	DB00168
KEGG	C11045 Y
ChEBI	CHEBI:2877 Y
ChEMBL	CHEMBL171679 Y
Jmol-3D images	Image 1
SMILES O=C(O)C[C@H](N)C(=O)N[C@H](C(=O)OC)Cc1ccccc1
InChI 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-/m0/s1 Y Key: IAOZJIPTCAWIRG-QWRGUYRKSA-N Y 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
Properties
Molecular formula	C14H18N2O5
Molar mass	294.3 g mol−1
Density	1.347 g/cm3
Melting point	246–247 °C
Boiling point	decomposes
Solubility in water	sparingly soluble
Solubility	slightly soluble in ethanol
Acidity (pKa)	4.5-6.0 [2]
Hazards
NFPA 704	1 1 0
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

Aspartame (APM; /ˈæspərteɪm/ or /əˈspɑrteɪm/) is an artificial, non-saccharide sweetener used as a sugar substitute in some foods and beverages. In the European Union, it is codified as E951. Aspartame is a methyl ester of the aspartic acid/phenylalanine dipeptide. It was first sold under the brand name NutraSweet; since 2009 it also has been sold under the brand name AminoSweet. It was first synthesized in 1965 and the patent expired in 1992.

The safety of aspartame has been the subject of several political and medical controversies, congressional hearings and internet hoaxes^[3][4][5] since its initial approval for use in food products by the U.S. Food and Drug Administration (FDA) in 1974. A 2007 medical review on the subject concluded that "the weight of existing scientific evidence indicates that aspartame is safe at current levels of consumption as a non-nutritive sweetener".^[6] However, because its breakdown products include phenylalanine, aspartame must be avoided by people with the genetic condition phenylketonuria (PKU).

Contents 1 Chemistry 2 Properties and use 3 Discovery and approval 4 Metabolism and phenylketonuria 5 Pregnancy and lactation 6 Economics 6.1 NutraSweet Company 6.2 Ajinomoto 6.3 Holland Sweetener Company 6.4 Competing products 7 Safety and approval controversies 8 Compendial status 9 References

Chemistry

Aspartame is a methyl ester of the dipeptide of the natural amino acids L-aspartic acid and L-phenylalanine. Under strongly acidic or alkaline conditions, aspartame may generate methanol by hydrolysis. Under more severe conditions, the peptide bonds are also hydrolyzed, resulting in the free amino acids.^[7]

While known aspects of synthesis are covered by patents, many details are proprietary.^[8] Two approaches to synthesis are used commercially. In the chemical synthesis, the two carboxyl groups of aspartic acid are joined into an anhydride, and the amino group is protected by a compound that will prevent further reactions of that group. Phenylalanine is methylated and combined with the N-protected aspartic anhydride, then the blocking group is removed from aspartic acid by acid hydrolysis. The drawback of this technique is that a byproduct, the bitter tasting β-form, is produced when the wrong carboxyl group from aspartic acid links to phenylalanine. A process using an enzyme from Bacillus thermoproteolyticus to catalyze the condensation of the chemically altered amino acids will produce high yields without the β-form byproduct. A variant of this method, which has not been used commercially, uses unmodified aspartic acid, but produces low yields. Methods for directly producing aspartyl-phenylalanine by enzymatic means, followed by chemical methylation, have also been tried, but not scaled for industrial production.^[9]

Properties and use

Beta-aspartame differs from aspartame based upon which carboxyl group of aspartate binds to the nitrogen of phenylalanine.

Aspartame, an artificial sweetener, is approximately 200 times sweeter than sucrose, or table sugar. Due to this property, even though aspartame produces four kilocalories of energy per gram when metabolized, the quantity of aspartame needed to produce a sweet taste is so small that its caloric contribution is negligible.^[6] The taste of aspartame and other artificial sweeteners differs from 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.^[8] The sweetness of aspartame lasts longer than sucrose, so it is often blended with other artificial sweeteners such as acesulfame potassium to produce an overall taste more like sugar.^[10] Aspartame can be synthesized from its constituent amino acids, L-phenylalanine and L-aspartate.

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.^[11]

Aspartame's major decomposition products are its cyclic dipeptide (diketopiperazine form), the de-esterified dipeptide (aspartyl-phenylalanine), and its constituent components, phenylalanine,^[12] aspartic acid,^[13] and methanol.^[14] At 180°C, aspartame undergoes decomposition to form a diketopiperazine (DKP) derivative.^[15]

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.

Descriptive analyses of solutions containing aspartame report a sweet aftertaste as well as bitter and off-flavour aftertastes.^[16]

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 accidentally discovered its sweet taste when he licked his finger, which had become contaminated with aspartame, to lift up a piece of paper.^[17][18]

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".^[19] The FDA sought to authenticate 15 of the submitted studies against the supporting data. In 1979, the Center for Food Safety and 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.^[19]

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 aspartame does not cause brain damage, but it recommended against approving aspartame at that time, citing unanswered questions about cancer in laboratory rats.^[19][20]

Citing data from a Japanese study that had not been available to the members of the PBOI,^[21] and after seeking advice from an expert panel that found fault with statistical analyses underlying the PBOI's hesitation, yet argued against approval,^[22] FDA commissioner Hayes approved aspartame for use in dry goods.^[23] In 1983, the 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.

Several European Union countries 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 Acceptable Daily Intake was appropriate, after reviewing yet another set of studies.^[24]

Metabolism and phenylketonuria

Upon ingestion, aspartame breaks down into natural residual components, including aspartic acid, phenylalanine, methanol,^[25] and further breakdown products including formaldehyde^[26] and formic acid, accumulation of the latter being suspected as the major cause of injury in methanol poisoning. Human studies show that formic acid is excreted faster than it is formed after ingestion of aspartate. In some fruit juices, higher concentrations of methanol can be found than the amount produced from aspartame in beverages.^[13]

High levels of the naturally-occurring essential amino acid phenylalanine are 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.^[27]

In the UK, foods that contain aspartame are legally required by the country's Food Standards Agency to 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 are also required to 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".^[28]

In Canada, foods that contain aspartame are legally required by the country to list the chemical among the product's ingredients 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.^[29]

Pregnancy and lactation

In a study done in 1979, the effect of aspartame ingestion on blood and milk amino acid levels in lactating women was tested. ^[30] In this study, six women from the ages of 20 to 29 with established lactation were studied after oral administration of aspartame or lactose (50 mg/kg body weight) in a random order, with the intent to study the differences in breast milk between the two. The study resulted with the conclusion that aspartame administration at 50 mg/kg body weight has a small effect upon the milk aspartate levels and although a small increase in aspartate time-effect scores was noted over the four-hour post-absorptive period, no significant difference was noted over the entire 24 hour watching period. ^[31]

Economics

Under the trade names Equal, NutraSweet, and Canderel, aspartame is an ingredient in approximately 6,000 consumer foods and 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 vitamin supplements, 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 for baking than other sweeteners, because it breaks down when heated and loses much of its sweetness. Aspartame is also one of the main sugar substitutes used by people with diabetes.

NutraSweet Company

In 1984, Monsanto Company 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.^[32] European use patents on aspartame expired starting in 1987,^[33] and the U.S. patent expired in 1992. Since then, the company has competed for market share with other manufacturers, including Ajinomoto, Merisant and the Holland Sweetener Company.

Ajinomoto

Many aspects of industrial synthesis of aspartame were established by Ajinomoto.^[8] In 2004, the market for aspartame, in which 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.^[34] Ajinomoto acquired its aspartame business in 2000 from Monsanto for $67M.^[35]

In 2008, Ajinomoto sued British supermarket chain Asda, part of Wal-Mart, for a malicious falsehood action concerning its aspartame product when the chemical was listed as excluded from the chain's product line, along with other "nasties".^[36] In July 2009, a British court found in favour of Asda.^[37] In June 2010, an appeals court reversed the decision, allowing Ajinomoto to pursue a case against Asda to protect aspartame's reputation.^[38] Asda said that it would continue to use the term "no nasties" on its own-label products,^[39] but the suit was settled in 2011 with ASDA choosing to remove references to aspartame from its packaging.^[40]

In November 2009, Ajinomoto announced a new brand name for its aspartame sweetener — AminoSweet.^[41]

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.^[42] Additionally, they developed a combination aspartame-acesulfame salt under the brand name Twinsweet.^[43] They left the sweetener industry in late 2006, because "global aspartame markets are facing structural oversupply, which has caused worldwide strong price erosion over the last five years", making the business "persistently unprofitable".^[44]

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.^[45] This, along with differences in marketing and changing consumer preferences, caused aspartame to lose market share to sucralose.^[46][47] In 2004, aspartame traded at about $30/kg and sucralose, which is roughly three times sweeter by weight, at around $300/kg.^[48]

Safety and approval controversies

Main article: Aspartame controversy

Aspartame has been found to be safe for human consumption by more than ninety countries worldwide,^[49][50] with FDA officials describing aspartame as "one of the most thoroughly tested and studied food additives the agency has ever approved" and its safety as "clear cut",^[51] but has been the subject of several controversies, hoaxes^[3] and health scares.^[52]

Problems with safety tests were found following the initial approval by the U.S. Food and Drug Administration (FDA) in 1974. Approval was rescinded the following year and after reviews and additional testing, final approval was granted in 1981. Allegations of conflicts of interest marred the FDA's approval of aspartame; question the quality of the initial research supporting its safety;^[53][54][55] The U.S. Government Accountability Office conducted reviews of 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.^[53][56]

A widely circulated email hoax cited aspartame as the cause of numerous diseases.^[57] The Center for Disease Control investigated and was unable to find any significant epidemiological associations to serious risk or harm.^[58]

The weight of existing scientific evidence indicates that aspartame is safe at current levels of consumption as a non-nutritive sweetener.^[6] Reviews conducted by regulatory agencies decades after aspartame was first approved have supported its continued availability.^[59]

Compendial status

• British Pharmacopoeia ^[60]
• United States Pharmacopeia ^[61]

References

1. ^ Budavari, Susan, ed. (1989). "861. Aspartame". The Merck Index (11th ed.). Rahway, NJ: Merck & Co.. p. 859. ISBN 91191028X. 
2. ^ Rowe, Raymond C. (2009). "Aspartame". Handbook of Pharmaceutical Excipients. pp. 11–12. ISBN 1-58212-058-7. 
3. ^ ^{a b} Aspartame on Snopes.com
4. ^ ACSH Debunks Internet Health Hoax
5. ^ A Web of Deceit
6. ^ ^{a b c} Magnuson BA, Burdock GA, Doull J et al (2007). "Aspartame: a safety evaluation based on current use levels, regulations, and toxicological and epidemiological studies". Critical Reviews in Toxicology 37 (8): 629–727. doi:10.1080/10408440701516184. PMID 17828671. 
7. ^ 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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v t e E numbers - 950-969 Colours (E100–199) Preservatives (E200–299) Antioxidants & Acidity regulators (E300–399) Thickeners, stabilisers & emulsifiers (E400–499) pH regulators & anti-caking agents (E500–599) Flavour enhancers (E600–699) Antibiotics (E700–799) Miscellaneous (E900–999) Additional chemicals (E1100–1599) Waxes (E900–909) Synthetic glazes (E910–919) Improving agents (E920–929) Packaging gases (E930–949) Sweeteners (E950–969) Foaming agents (E990–999) Acesulfame K (E950) Aspartame (E951) Cyclamate (E952) Isomalt (E953) Saccharin (E954) Sucralose (E955) Alitame (E956) Thaumatin (E957) Neohesperidin dihydrochalcone (E959) Neotame (E961) Aspartame-acesulfame salt (E962) Maltitol (E965) Lactitol (E966) Xylitol (E967)

This entry is from Wikipedia, the leading user-contributed encyclopedia. It may not have been reviewed by professional editors (see full disclaimer)

Dansk (Danish)
n. - aspartam (sødemiddel)

Nederlands (Dutch)
zoetmiddel

Français (French)
n. - aspartame

Deutsch (German)
n. - Aspartam (kalorienarmer Süßstoff)

Ελληνική (Greek)
n. - γλυκαντική ουσία

Italiano (Italian)
aspartame

Português (Portuguese)
n. - aspartame (m) (Quím.)

Русский (Russian)
аспартам

Español (Spanish)
n. - endulzador artificial, edulcorante

Svenska (Swedish)
n. - aspartam

中文（简体）(Chinese (Simplified))
天冬甜素, 天冬甜精, 一种低热量代糖物质

中文（繁體）(Chinese (Traditional))
n. - 天冬甜素, 天冬甜精, 一種低熱量代糖物質

한국어 (Korean)
n. - 아스파테임(설탕의 약 200배 단맛이 나는 인공 감미료)

日本語 (Japanese)
n. - アスパルテーム

עברית (Hebrew)
n. - ‮חומר מתוק מאד דל-קלוריות המשמש כתחליף לסוכר, אספרטיים (ממתיק)‬

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