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
  • InChI=1S/C14H25N3O4S/c1-7(16-11(21)8(15)6-9(18)19)10(20)17-12-13(2,3)22-14(12,4)5/h7-8,12H,6,15H2,1-5H3,(H,16,21)(H,17,20)(H,18,19)/t7-,8+/m1/s1 Yes check.svgY
    Key: IVBOUFAWPCPFTQ-SFYZADRCSA-N Yes check.svgY
  • InChI=1/C14H25N3O4S/c1-7(16-11(21)8(15)6-9(18)19)10(20)17-12-13(2,3)22-14(12,4)5/h7-8,12H,6,15H2,1-5H3,(H,16,21)(H,17,20)(H,18,19)/t7-,8+/m1/s1
    Key: IVBOUFAWPCPFTQ-SFYZADRCBL
  • CC(C(=O)NC1C(SC1(C)C)(C)C)NC(=O)C(CC(=O)O)N
  • O=C(NC1C(SC1(C)C)(C)C)[C@H](NC(=O)[C@@H](N)CC(=O)O)C
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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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 Danisco has withdrawn its petition for using alitame as a sweetening agent or flavoring in food in US. [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

<span class="mw-page-title-main">Aspartame</span> Artificial non-saccharide sweetener

Aspartame is an artificial non-saccharide sweetener commonly used as a sugar substitute in foods and beverages. 200 times sweeter than sucrose, it is a methyl ester of the aspartic acid/phenylalanine dipeptide with brand names NutraSweet, Equal, and Canderel. Discovered in 1965, aspartame was approved by the US Food and Drug Administration (FDA) in 1974 and re-approved in 1981 after its initial approval was briefly revoked.

<span class="mw-page-title-main">Sucralose</span> Non-nutritive sweetener

Sucralose is an artificial sweetener and sugar substitute. As the majority of ingested sucralose is not metabolized by the body, it adds very little food energy. In the European Union, it is also known under the E number E955. It is produced by chlorination of sucrose, selectively replacing three of the hydroxy groups—in the C1 and C6 positions of the fructose portion and the C4 position of the glucose portion—to give a 1,6-dichloro-1,6-dideoxyfructose–4-chloro-4-deoxygalactose disaccharide. Sucralose is about 600 times sweeter than sucrose, 3 times as sweet as both aspartame and acesulfame potassium, and 2 times as sweet as sodium saccharin.

<span class="mw-page-title-main">Fructose</span> Simple ketonic monosaccharide found in many plants

Fructose, or fruit sugar, is a ketonic simple sugar 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 by the gut directly into the blood of the portal vein during digestion. The liver then converts most fructose and galactose into glucose for distribution in the bloodstream or deposition into glycogen.

<span class="mw-page-title-main">Sugar substitute</span> Sugarless food additive intended to provide a sweet taste

A sugar substitute is a food additive that provides a sweetness like that of sugar while containing significantly less food energy than sugar-based sweeteners, making it a zero-calorie or low-calorie sweetener. Artificial sweeteners may be derived through manufacturing of plant extracts or processed by chemical synthesis. Sugar substitute products are commercially available in various forms, such as small pills, powders and packets.

<span class="mw-page-title-main">Xylitol</span> Synthetic sweetener

Xylitol is a chemical compound with the formula C
5
H
12
O
5
, or HO(CH2)(CHOH)3(CH2)OH; specifically, one particular stereoisomer with that structural formula. It is a colorless or white crystalline solid. It is classified as a polyalcohol and a sugar alcohol, specifically an alditol. Of the common sugar alcohols, only sorbitol is more soluble in water.

<span class="mw-page-title-main">Saccharin</span> Chemical compound

Saccharin, also called saccharine, benzosulfimide, or E954, or used in saccharin sodium or saccharin calcium forms, is a non-nutritive artificial sweetener. Saccharin is a sultam that is about 500 times sweeter than sucrose, but has a bitter or metallic aftertaste, especially at high concentrations. It is used to sweeten products, such as drinks, candies, baked goods, tobacco products, excipients, and for masking the bitter taste of some medicines. It appears as white crystals and is odorless.

<span class="mw-page-title-main">Acesulfame potassium</span> Calorie-free sugar substitute

Acesulfame potassium, also known as acesulfame K or Ace K, is a synthetic 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. 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.

<span class="mw-page-title-main">Diet soda</span> Soft drink with little or no sugar or calories

Diet sodas are soft drinks which contain little or no sugar or calories. First introduced onto the market in 1949, diet sodas are typically marketed for those with diabetes or who wish to reduce their sugar or caloric intake.

<span class="mw-page-title-main">Dipeptide</span> Shortest peptide molecule, containing two amino acids joined by a single peptide bond

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.

<span class="mw-page-title-main">Neotame</span> Artificial sweetener

Neotame, also known by the brand name Newtame, is a non-caloric artificial sweetener and aspartame analog by NutraSweet. By mass, it is 7,000 to 13,000 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.

<span class="mw-page-title-main">Monellin</span> Protein

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.

<span class="mw-page-title-main">Lactisole</span> Chemical compound

Lactisole is the sodium salt and commonly supplied form of 2-(4-methoxyphenoxy)propionic acid, a natural carboxylic acid found in roasted coffee beans. Like gymnemic acid, it has the property of masking sweet flavors and is used for this purpose in the food industry.

<span class="mw-page-title-main">Sweetness</span> Basic taste

Sweetness is a basic taste most commonly perceived when eating foods rich in sugars. Sweet tastes are generally regarded as pleasurable. 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, aspartame, sucralose and stevia. Other compounds, such as miraculin, may alter perception of sweetness itself.

<span class="mw-page-title-main">High-fructose corn syrup</span> Processed corn syrup

High-fructose corn syrup (HFCS), also known as glucose–fructose, isoglucose and glucose–fructose syrup, is a sweetener made from corn starch. As in the production of conventional corn syrup, the starch is broken down into glucose by enzymes. To make HFCS, the corn syrup is further processed by D-xylose isomerase to convert some of its glucose into fructose. HFCS was first marketed in the early 1970s by the Clinton Corn Processing Company, together with the Japanese Agency of Industrial Science and Technology, where the enzyme was discovered in 1965.

<span class="mw-page-title-main">Brazzein</span> Protein

Brazzein is a sweet-tasting protein that occurs naturally in oubli, a fruit native to the Atlantic coastal areas of Central Africa. Brazzein was first isolated in 1994 by scientists at the University of Wisconsin–Madison. It is roughly 500 to 2000 times sweeter than sucrose.

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.

<span class="mw-page-title-main">Steviol glycoside</span> Sweet chemicals derived from the Stevia plant

Steviol glycosides are the chemical compounds responsible for the sweet taste of the leaves of the South American plant Stevia rebaudiana (Asteraceae) and the main ingredients of many sweeteners marketed under the generic name stevia and several trade names. They also occur in the related species S. phlebophylla and in the plant Rubus chingii (Rosaceae).

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.

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

<span class="mw-page-title-main">Advantame</span> Chemical compound

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. Bibcode:1995JChEd..72..671E. 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   978-0-470-00955-0. 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.