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 Wikipedia does not have an article with this exact name. ... Image File history File links Size of this preview: 769 × 600 pixelsFull resolution (1100 × 858 pixel, file size: 203 KB, MIME type: image/png) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Aspartame ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... NutraSweet is the company that makes and sells aspartame, an artificial sugar substitute. ... CANDEREL is a popular brand of artificial sweetener made mainly from aspartame. ... EQUAL is a popular brand of artificial sweetener made mainly from aspartame. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... A chemical formula is an easy way of expressing information about the atoms that constitute a particular chemical compound. ... Molar mass is the mass of one mole of a chemical element or chemical compound. ... The melting point of a solid is the temperature range at which it changes state from solid to liquid. ...
Boiling point	decomposes Italic text This article is about the boiling point of liquids. ...
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) (pronounced /ˈæspɚteɪm/ or /əˈspɑrteɪm/) is the name for an artificial, non-saccharide sweetener, aspartyl-phenylalanine-1-methyl ester; i.e., a methyl ester of the dipeptide of the amino acids aspartic acid and phenylalanine. NFPA 704 is a standard maintained by the U.S. National Fire Protection Association. ... Image File history File links NFPA_704. ... The plimsoll symbol as used in shipping In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals exactly). ... an essential structural component of living cells and source of energy for animals; includes simple sugars with small molecules as well as macromolecular substances; are classified according to the number of monosaccharide groups they contain. ... It has been suggested that this article or section be merged with Sugar substitute. ... For other uses, see Ester (disambiguation). ... A dipeptide is a molecule consisting of two amino acids joined by a single peptide bond. ... This article is about the class of chemicals. ... Aspartic acid (abbreviated as Asp or D; Asx or B represent either aspartic acid or asparagine[1] ) is an α-amino acid with the chemical formula HO2CCH(NH2)CH2CO2H. The L-isomer is a protonated varient of one of the 20 proteinogenic amino acids, i. ... Phenyl alanine is an α-amino acid with the formula HO2CCH(NH2)CH2C6H5. ...

This sweetener is marketed under a number of trademark names, including Tropicana Slim, 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 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 people with diabetes. EQUAL is a popular brand of artificial sweetener made mainly from aspartame. ... NutraSweet is the company that makes and sells aspartame, an artificial sugar substitute. ... CANDEREL is a popular brand of artificial sweetener made mainly from aspartame. ... A soft drink is a drink that contains no alcohol. ... Retinol (one vitamer of Vitamin A) A vitamin is an organic compound required as a nutrient in tiny amounts by an organism. ... Some examples of baked food. ... Chemical decomposition or analysis is the fragmentation of a chemical compound into elements or smaller compounds. ... For the mathematical constant see: E (mathematical constant). ... For the disease characterized by excretion of large amounts of very dilute urine, see diabetes insipidus. ...

Aspartame is a subject of a public controversy due to possible health risks, and has consequently lost market share in recent years to sucralose (Splenda).^[2] See Aspartame controversy. Sucralose is an artificial sweetener. ... The artificial sweetener aspartame has been the subject of a vigorous public controversy regarding its safety and the circumstances around its approval. ...

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 may generate methanol by hydrolysis. Under more severe conditions, the peptide bonds are also hydrolyzed, resulting in the free amino acids.^[3] In chemistry a methyl-group is a hydrophobic Alkyl functional group which is derived from methane (CH4). ... For other uses, see Ester (disambiguation). ... A dipeptide is a molecule consisting of two amino acids joined by a single peptide bond. ... This article is about the class of chemicals. ... Aspartic acid (abbreviated as Asp or D; Asx or B represent either aspartic acid or asparagine[1] ) is an α-amino acid with the chemical formula HO2CCH(NH2)CH2CO2H. The L-isomer is a protonated varient of one of the 20 proteinogenic amino acids, i. ... Phenyl alanine is an α-amino acid with the formula HO2CCH(NH2)CH2C6H5. ... For other uses, see acid (disambiguation). ... Acids and bases: Acid-base extraction Acid-base reaction Acid dissociation constant Acidity function Buffer solutions pH Proton affinity Self-ionization of water Acids: Lewis acids Mineral acids Organic acids Strong acids Superacids Weak acids Bases: Lewis bases Organic bases Strong bases Superbases Non-nucleophilic bases Weak bases edit In... Methanol, also known as methyl alcohol, carbinol, wood alcohol, wood naphtha or wood spirits, is a chemical compound with chemical formula CH3OH (often abbreviated MeOH). ... Hydrolysis is a chemical reaction or process in which a chemical compound is broken down by reaction with water. ... A peptide bond is a chemical bond that is formed between two molecules when the carboxyl group of one molecule reacts with the amino group of the other molecule, releasing a molecule of water (H2O). ... Hydrolysis is a chemical process in which a molecule is cleaved into two parts by the addition of a molecule of water. ...

Properties and use

Aspartame is an artificial sweetener because it is 180 times as sweet as 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. This article is about sugar as food and as an important and widely-traded commodity. ... For other uses, see Concentration (disambiguation). ... This article is about sugar as food and as an important and widely-traded commodity. ... Peptides (from the Greek πεπτος, digestible), are the family of short molecules formed from the linking, in a defined order, of various α-amino acids. ... BIC pen cap, about 1 gram. ... Chemical structure of Acesulfame potassium Acesulfame potassium is a calorie-free artificial sweetener, also known as Acesulfame K or Ace K, and marketed under the trade names Sunett and Sweet One. ... Chemical structure of Acesulfame potassium Acesulfame potassium is a calorie-free artificial sweetener, also known as Acesulfame K or Ace K, and marketed under the trade names Sunett and Sweet One. ...

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] Peptides (from the Greek πεπτος, digestible), are the family of short molecules formed from the linking, in a defined order, of various α-amino acids. ... Hydrolysis is a chemical process in which a molecule is cleaved into two parts by the addition of a molecule of water. ... For other uses, see PH (disambiguation). ... For other uses, see FAT. Fats consist of a wide group of compounds that are generally soluble in organic solvents and largely insoluble in water. ... Maltodextrin is a moderately sweet polysaccharide used as a food additive, unrelated to barley malt. ... Impact from a water drop causes an upward rebound jet surrounded by circular capillary waves. ... For other uses, see PH (disambiguation). ... Half-Life For a quantity subject to exponential decay, the half-life is the time required for the quantity to fall to half of its initial value. ... Half-Life For a quantity subject to exponential decay, the half-life is the time required for the quantity to fall to half of its initial value. ... In cooking, Syrup (from the Arabian šarab via Latin siropus) is a thick, viscous liquid, containing a large amount of dissolved sugar, but showing little tendency to deposit crystals. ... Soda fountain is a North American term referring to the carbonated drink dispensers found in fast food restaurants and convenience stores in the US and Canada. ... Saccharin[2] is the oldest artificial sweetener. ...

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. Powder is a substance that has been crushed into very fine grains. ... The general structure of an amine Amines are organic compounds and a type of functional group that contain nitrogen as the key atom. ... The Maillard reaction is a chemical reaction between an amino acid and a reducing sugar, usually requiring the addition of heat. ... An aldehyde. ... An aroma compound, also known as odorant, aroma, fragrance, flavor, is a chemical compound that has a smell or odor. ... An acetal is a functional group or molecule containing the functional group of a carbon bonded to two -OR groups. ...

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] Year 1965 (MCMLXV) was a common year starting on Friday (link will display full calendar) of the 1965 Gregorian calendar. ... G.D. Searle & Company was a company focusing on life sciences, specifically pharmaceuticals, agriculture, and animal health. ... In chemistry, chemical synthesis is purposeful execution of chemical reactions in order to get a product, or several products. ... Endoscopic images of a duodenal ulcer. ...

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^[6]. 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^{[citation needed]}. 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^{[citation needed]}. The Bressler Report^[7] compared all the available raw data and summary data against the manufacturer's FDA submission and found missing raw data, errors and discrepancies in available data, but FDA chose to ignore Bressler's report. 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. Searle's Chief Operating Officer, Donald Rumsfeld, reapplied for FDA certification immediately after U.S. President Ronald Reagan took office.^[8] 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.^[9] 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. “FDA” redirects here. ... A brain tumor is any mass created by an abnormal and uncontrolled growth of cells either found in the brain (neurons, glial cells, epithelial cells, myelin producing cells, etc. ... For other uses, see Brain (disambiguation). ... Cancer is a class of diseases or disorders characterized by uncontrolled division of cells and the ability of these to spread, either by direct growth into adjacent tissue through invasion, or by implantation into distant sites by metastasis (where cancer cells are transported through the bloodstream or lymphatic system). ... A Chief Operating Officer (COO) is a corporate officer responsible for managing the day-to-day activities of the corporation. ... Donald Henry Rumsfeld (born July 9, 1932) is a businessman, a U.S. Republican politician, the 13th Secretary of Defense under President Gerald Ford from 1975 to 1977, and the 21st Secretary of Defense under President George W. Bush from 2001 to 2006. ... Reagan redirects here. ...

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.^[10] 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”.^[11] The Monsanto Company (NYSE: MON) is a multinational agricultural biotechnology corporation. ... NutraSweet is the company that makes and sells aspartame, an artificial sugar substitute. ... is the 145th day of the year (146th in leap years) in the Gregorian calendar. ... Year 2000 (MM) was a leap year starting on Saturday. ... For other uses, see Patent (disambiguation). ... Ajinomoto Ajinomoto Co. ...

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 Adequate Daily Intake was appropriate, after reviewing yet another set of studies.^[12]

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.^[13] WHO redirects here. ...

Metabolism

Upon ingestion, aspartame breaks down into several residual chemicals, including aspartic acid, phenylalanine, methanol, and further breakdown products including formaldehyde,^[14] formic acid, and a diketopiperazine. 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) Aspartic acid (abbreviated as Asp or D; Asx or B represent either aspartic acid or asparagine[1] ) is an α-amino acid with the chemical formula HO2CCH(NH2)CH2CO2H. The L-isomer is a protonated varient of one of the 20 proteinogenic amino acids, i. ... Phenyl alanine is an α-amino acid with the formula HO2CCH(NH2)CH2C6H5. ... Methanol, also known as methyl alcohol, carbinol, wood alcohol, wood naphtha or wood spirits, is a chemical compound with chemical formula CH3OH (often abbreviated MeOH). ... Formaldehyde is the chemical compound with the formula H2CO. It is the simplest aldehyde-- an organic compound containing a terminal carbonyl group: it consists of exactly one carbonyl. ... Formic acid (systematically called methanoic acid) is the simplest carboxylic acid. ... Diketopirerazine (DKP) is a chemical compound. ... The artificial sweetener aspartame has been the subject of a vigorous public controversy regarding its safety and the circumstances around its approval. ...

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. An essential amino acid or indispensable amino acid is an amino acid that cannot be synthesized de novo by the organism (usually referring to humans), and therefore must be supplied in the diet. ... Phenyl alanine is an α-amino acid with the formula HO2CCH(NH2)CH2C6H5. ... Phenylketonuria (PKU) is an autosomal recessive genetic disorder characterized by a deficiency in the enzyme phenylalanine hydroxylase (PAH). ...

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.^[15]

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.^[16][17][18] 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.^[19][20] The artificial sweetener aspartame has been the subject of a vigorous public controversy regarding its safety and the circumstances around its approval. ... A brain tumor is any intracranial tumor created by abnormal and uncontrolled cell division, normally either in the brain itself (neurons, glial cells (astrocytes, oligodendrocytes, ependymal cells), lymphatic tissue, blood vessels), in the cranial nerves (myelin-producing Schwann cells), in the brain envelopes (meninges), skull, pituitary and pineal gland, or... Skin lesions caused by Chickenpox A lesion is any abnormal tissue found on or in an organism, usually damaged by disease or trauma. ... This article is about lymphoma in humans. ... A conflict of interest is a situation in which someone in a position of trust, such as a lawyer, a politician, or an executive or director of a corporation, has competing professional or personal interests. ... Donald Henry Rumsfeld (born July 9, 1932) is a businessman, a U.S. Republican politician, the 13th Secretary of Defense under President Gerald Ford from 1975 to 1977, and the 21st Secretary of Defense under President George W. Bush from 2001 to 2006. ...

References