Alitame

Last updated
Alitame
Alitame.svg
Names
IUPAC name
(3S)-3-amino-4-[ [(1R)-1-methyl-2-oxo-2-[(2,2,4,4-tetramethyl-3-thietanyl)amino]ethyl]amino]-4-oxobutanoic acid
Other names
L-alpha-Aspartyl-N-(2,2,4,4-tetramethyl-3-thietanyl)-D-alaninamide
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
E number E956 (glazing agents, ...)
PubChem CID
UNII
Properties
C14H25N3O4S
Molar mass 331.431
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Alitame is an aspartic acid-containing dipeptide sweetener. It was developed by Pfizer in the early 1980s and currently marketed in some countries under the brand name Aclame. [1] Most dipeptides are not sweet, but the unexpected discovery of aspartame in 1965 led to a search for similar compounds that shared its sweetness. Alitame is one such second-generation dipeptide sweetener. Neotame, developed by the owners of the NutraSweet brand, is another.

Alitame is about 2000 times sweeter than sucrose (table sugar), [2] about 10 times sweeter than aspartame, and has no aftertaste. Its half-life under hot or acidic conditions is about twice as long as aspartame's, although some other artificial sweeteners, including saccharin and acesulfame potassium, are more stable yet. Unlike aspartame, alitame does not contain phenylalanine, and can therefore be used by people with phenylketonuria.

Alitame has approved for use in Mexico, Australia, New Zealand and China. Danisco has withdrawn its petition for using alitame as a sweetening agent or flavoring in food in USA. [3]

Sweeny also addresses a compound with a sweetness of 1200 x sucrose in his review, [4] in U.S. Patent 4,411,925 based on an NH-CH(cyclopropyl)tert-butyl (Ex 6). Ex 5, with NH-CH(cyclopropyl)2 is also 1200 x sucrose. These are good basis for 2nd class picks. Ex 16 is for Alitame proper. Although, in Ex 17, oxidation to the sulfonyl can reduce activity to 1000.

Related Research Articles

Aspartame artificial non-saccharide sweetener

Aspartame is an artificial non-saccharide sweetener 200 times sweeter than sucrose, and is commonly used as a sugar substitute in foods and beverages. It is a methyl ester of the aspartic acid/phenylalanine dipeptide with the trade names NutraSweet, Equal, and Canderel. Aspartame was first made in 1965 and approved for use in food products by the U.S. Food and Drug Administration (FDA) in 1981.

Sucralose

Sucralose is an artificial sweetener and sugar substitute. The majority of ingested sucralose is not broken down by the body, so it is noncaloric. In the European Union, it is also known under the E number E955. It is produced by chlorination of sucrose. Sucralose is about 320 to 1,000 times sweeter than sucrose, three times as sweet as both aspartame and acesulfame potassium, and twice as sweet as sodium saccharin. Evidence of benefit is lacking for long-term weight loss with some data supporting weight gain and heart disease risks.

Fructose A simple ketonic monosaccharide found in many plants

Fructose, or fruit sugar, is a simple ketonic monosaccharide found in many plants, where it is often bonded to glucose to form the disaccharide sucrose. It is one of the three dietary monosaccharides, along with glucose and galactose, that are absorbed directly into blood during digestion. Fructose was discovered by French chemist Augustin-Pierre Dubrunfaut in 1847. The name "fructose" was coined in 1857 by the English chemist William Allen Miller. Pure, dry fructose is a sweet, white, odorless, crystalline solid, and is the most water-soluble of all the sugars. Fructose is found in honey, tree and vine fruits, flowers, berries, and most root vegetables.

Sugar substitute Food additive

A sugar substitute is a food additive that provides a sweet taste like that of sugar while containing significantly less food energy than sugar-based sweeteners, making it a zero-calorie (non-nutritive) or low-calorie sweetener. Artificial sweeteners may be derived through manufacturing of plant extracts or processed by chemical synthesis. Sugar alcohols such as erythritol, xylitol, and sorbitol are derived from sugars. In 2017, sucralose was the most common sugar substitute used in the manufacture of foods and beverages; it had 30% of the global market, which was projected to be valued at $2.8 billion by 2021.

Aspartic acid Amino acid

Aspartic acid (symbol Asp or D; the ionic form is known as aspartate), is an α-amino acid that is used in the biosynthesis of proteins. Like all other amino acids, it contains an amino group and a carboxylic acid. Its α-amino group is in the protonated –NH+
3
form under physiological conditions, while its α-carboxylic acid group is deprotonated −COO under physiological conditions. Aspartic acid has an acidic side chain (CH2COOH) which reacts with other amino acids, enzymes and proteins in the body. Under physiological conditions (pH 7.4) in proteins the side chain usually occurs as the negatively charged aspartate form, −COO. It is a non-essential amino acid in humans, meaning the body can synthesize it as needed. It is encoded by the codons GAU and GAC.

Saccharin

Sodium saccharin is an artificial sweetener with effectively no food energy. It is about 300–400 times as sweet as sucrose but has a bitter or metallic aftertaste, especially at high concentrations. Saccharin is used to sweeten products such as drinks, candies, cookies, and medicines.

Acesulfame potassium chemical compound

Acesulfame potassium, also known as acesulfame K or Ace K, is a calorie-free sugar substitute often marketed under the trade names Sunett and Sweet One. In the European Union, it is known under the E number E950. It was discovered accidentally in 1967 by German chemist Karl Clauss at Hoechst AG. In chemical structure, acesulfame potassium is the potassium salt of 6-methyl-1,2,3-oxathiazine-4(3H)-one 2,2-dioxide. It is a white crystalline powder with molecular formula C
4
H
4
KNO
4
S
and a molecular weight of 201.24 g/mol.

Dietdrinks or light drinks are sugar-free, artificially sweetened versions of carbonated beverages with virtually no calories. They are generally marketed toward health-conscious people, diabetics, athletes, and other people who want to lose weight, improve physical fitness, or reduce their sugar intake.

Dipeptide

A dipeptide is an organic compound derived from two amino acids. The constituent amino acids can be the same or different. When different, two isomers of the dipeptide are possible, depending on the sequence. Several dipeptides are physiologically important, and some are both physiologically and commercially significant. A well known dipeptide is aspartame, an artificial sweetener.

Neotame

Neotame, also known by the trade name Newtame, is a non-caloric artificial sweetener and aspartame analog by NutraSweet. By mass, it is 8000 times sweeter than sucrose. It has no notable off-flavors when compared to sucrose. It enhances original food flavors. It can be used alone, but is often mixed with other sweeteners to increase their individual sweetness and decrease their off-flavors. It is chemically somewhat more stable than aspartame. Its use can be cost effective in comparison to other sweeteners as smaller amounts of neotame are needed.

Monellin

Monellin, a sweet protein, was discovered in 1969 in the fruit of the West African shrub known as serendipity berry ; it was first reported as a carbohydrate. The protein was named in 1972 after the Monell Chemical Senses Center in Philadelphia, U.S.A., where it was isolated and characterized.

Lactisole

Lactisole is a carboxylic acid salt. Like gymnemic acid, it is a sweet inhibitor or taste modifier.

Sweetness Basic taste

Sweetness is a basic taste most commonly perceived when eating foods rich in sugars. Sweet tastes are generally regarded as pleasurable, except when in excess. In addition to sugars like sucrose, many other chemical compounds are sweet, including aldehydes, ketones, and sugar alcohols. Some are sweet at very low concentrations, allowing their use as non-caloric sugar substitutes. Such non-sugar sweeteners include saccharin and aspartame. Other compounds, such as miraculin, may alter perception of sweetness itself.

Brazzein

Brazzein is a sweet-tasting protein extracted from the West African fruit of the climbing plant Oubli. It was first isolated by the University of Wisconsin–Madison in 1994.

Fruit2O, formerly manufactured by Kraft, is a lightly flavored, non-carbonated water beverage introduced in 1999. Fruit2o was introduced to compete not only with the bottled water market but also with the soft drink market. Sunny Delight Beverages purchased the Veryfine Products line from Kraft in 2007.

The artificial sweetener aspartame has been the subject of several controversies since its initial approval by the U.S. Food and Drug Administration (FDA) in 1974. The FDA approval of aspartame was highly contested, beginning with suspicions of its involvement in brain cancer, alleging that the quality of the initial research supporting its safety was inadequate and flawed, and that conflicts of interest marred the 1981 approval of aspartame, previously evaluated by two FDA panels that concluded to keep the approval on hold before further investigation. In 1987, the U.S. Government Accountability Office concluded that the food additive approval process had been followed properly for aspartame. The irregularities fueled a conspiracy theory, which the "Nancy Markle" email hoax circulated, along with claims—counter to the weight of medical evidence—that numerous health conditions are caused by the consumption of aspartame in normal doses.

Gymnemic acids are a class of chemical compounds isolated from the leaves of Gymnema sylvestre (Asclepiadaceae). They are anti-sweet compounds, or sweetness inhibitors. After chewing the leaves, solutions sweetened with sugar taste like water.

Phenylacetaldehyde

Phenylacetaldehyde is an organic compound used in the synthesis of fragrances and polymers. Phenylacetaldehyde is an aldehyde that consists of acetaldehyde bearing a phenyl substituent; the parent member of the phenylacetaldehyde class of compounds. It has a role as a human metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite. It is an alpha-CH2-containing aldehyde and a member of phenylacetaldehydes.

Suosan is calorie-free artificial sweetener derived from β-alanine, discovered in 1948 by Petersen et Muller.

Advantame

Advantame is a non-caloric artificial sweetener and aspartame analog by Ajinomoto. By mass, it is about 20 000 times sweeter than sucrose and about 110 times sweeter than aspartame. It has no notable off-flavors when compared to sucrose and tastes sweet a bit longer than aspartame and is chemically more stable. It can be blended with many other natural and artificial sweeteners.

References

  1. Ellis, J. W. (1995). "Overview of Sweeteners". Journal of Chemical Education. 72 (8): 671–675. doi:10.1021/ed072p671.
  2. Laura Halpin Rinsky; Glenn Rinsky (2009). The Pastry Chef's Companion: A Comprehensive Resource Guide for the Baking and Pastry Professional . Chichester: John Wiley & Sons. pp.  5. ISBN   0-470-00955-1. OCLC   173182689.
  3. "Notice of withdrawal of petition: docket No. FDA-1986-F-0277 (formerly docket No. 1986F-0364)" (pdf). Food and Drug Administration.
  4. Sweeny, James G.; D'Angelo, Lihong L.; Ricks, Edith A.; Iacobucci, Guillermo A. (1995). "Discovery and Synthesis of a New Series of High-Potency L-Aspartyl-D-.alpha.-aminoalkanoyl-(S)-.alpha.-alkylbenzylamide Sweeteners". Journal of Agricultural and Food Chemistry. 43 (8): 1969–1976. doi:10.1021/jf00056a003. ISSN   0021-8561.