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Acesulfame potassium

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Acesulfame potassium
Acesulfame potassium
Acesulfame potassium
Ball-and-stick model of acesulfame potassium
Ball-and-stick model of acesulfame potassium
Names
IUPAC name potassium 6-methyl-2,2-dioxo-2H-1,2λ,3-oxathiazin-4-olate
Other names Acesulfame K Ace K
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.054.269 Edit this at Wikidata
EC Number
  • 259-715-3
E number E950 (glazing agents, ...)
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C4H5NO4S.K/c1-3-2-4(6)5-10(7,8)9-3;/h2H,1H3,(H,5,6);/q;+1Key: WBZFUFAFFUEMEI-UHFFFAOYSA-N
  • InChI=1/C4H5NO4S.K/c1-3-2-4(6)5-10(7,8)9-3;/h2H,1H3,(H,5,6);/q;+1Key: WBZFUFAFFUEMEI-UHFFFAOYAZ
SMILES
  • .C\C1=C\C(=O)NS(=O)(=O)O1
Properties
Chemical formula C4H4KNO4S
Molar mass 201.242
Appearance white crystalline powder
Density 1.81 g/cm
Melting point 225 °C (437 °F; 498 K)
Solubility in water 270 g/L at 20 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Acesulfame potassium is a calorie-free artificial sweetener, also known as Acesulfame K or Ace K (K being the symbol for potassium), and marketed under the trade names Sunett and Sweet One. In the European Union, it is known under the E number (additive code) E950. It was discovered accidentally in 1967 by German chemist Karl Clauss at Hoechst AG (now Nutrinova). 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 C4H4KNO4S and a molecular weight of 201.24 g/mol.

Properties

Acesulfame K is 180-200 times sweeter than sucrose (table sugar), as sweet as aspartame, about half as sweet as saccharin, and one-quarter as sweet as sucralose. Like saccharin, it has a slightly bitter aftertaste, especially at high concentrations. Kraft Foods has patented the use of sodium ferulate to mask acesulfame's aftertaste. Acesulfame K is often blended with other sweeteners (usually sucralose or aspartame). These blends are reputed to give a more sugar-like taste whereby each sweetener masks the other's aftertaste, and/or exhibits a synergistic effect by which the blend is sweeter than its components.

Unlike aspartame, acesulfame K is stable under heat, even under moderately acidic or basic conditions, allowing it to be used in baking, or in products that require a long shelf life. In carbonated drinks, it is almost always used in conjunction with another sweetener, such as aspartame or sucralose. It is also used as a sweetener in protein shakes and pharmaceutical products, especially chewable and liquid medications, where it can make the active ingredients more palatable.

Discovery

Acesulfame Potassium was developed after the accidental discovery of a similar compound (5,6-dimethyl-1,2,3-oxathiazin-4(3H)-one 2,2-dioxide) in 1967 by Karl Clauss and Harald Jensen at Hoechst AG. After accidentally dipping his fingers into the chemicals that he was working with, Clauss licked them to pick up a piece of paper. Subsequent research showed that a number of compounds with the same basic ring structure had varying levels of sweetness. 6-methyl-1,2,3-oxathiazine-4(3H)-one 2,2-dioxide had particularly favourable taste characteristics and was relatively easy to synthesize, so it was singled out for further research, and received its generic name (Acesulfame-K) from the World Health Organization in 1978.

Safety

As with other artificial sweeteners, there is concern over the safety of acesulfame potassium. Although studies of these sweeteners show varying and controversial degrees of dietary safety, the United States Food and Drug Administration (US FDA) has approved their general use. Critics say acesulfame potassium has not been studied adequately and may be carcinogenic, although these claims have been dismissed by the US FDA and by equivalent authorities in the European Union.

Some potential effects associated with Acesulfame K have appeared in animal studies. Acesulfame K has been shown to stimulate dose-dependent insulin secretion in rats, though no hypoglycemia was observed.

One rodent study showed no increased incidence of tumors in response to administration of acesulfame K. In this study, conducted by the National Toxicology Program, 60 rats were given acesulfame K for 40 weeks, making up as much as 3% of their total diet (which would be equivalent to a human consuming 1,343 12-oz cans of artificially sweetened soda every day). There was no sign that these (or lower) levels of acesulfame K increased the rats' risk of cancer or other neoplasms. Further research in terms of food safety has been recommended.

Compendial status

See also

References

  1. "Natural Products Expo/SupplyExpo Ingredient Standards & Guidelines". Penton Media, Inc. Retrieved 23 Feb 2010.
  2. Clauss K., Jensen H. (1973). "Oxathiazinone Dioxides - A New Group of Sweetening Agents". Angewandte Chemie International Edition. 12 (11): 869–876. doi:10.1002/anie.197308691.
  3. David J. Ager, David P. Pantaleone, Scott A. Henderson, Alan R. Katritzky, Indra Prakash, D. Eric Walters (1998). "Commercial, Synthetic Nonnutritive Sweeteners" (PDF). 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  4. United States Patent 5,336,513
  5. http://www.who.int/prequal/trainingresources/pq_pres/TrainingZA-April07/Excipients.ppt
  6. ^ Nabors, Lyn O'Brien; Lyn O'Brien-Nabors (2001). Alternative sweeteners. New York, N.Y: Marcel Dekker. p. 13. ISBN 0-8247-0437-1.{{cite book}}: CS1 maint: multiple names: authors list (link)
  7. Williams, Richard J.; Goldberg, Israel (1991). Biotechnology and food ingredients. New York: Van Nostrand Reinhold. ISBN 0-442-00272-6.{{cite book}}: CS1 maint: multiple names: authors list (link)
  8. Newton, David E. (2007). Food Chemistry (New Chemistry). New York: Facts on File. p. 69. ISBN 0-8160-5277-8.
  9. Kroger M, Meister K, Kava R (2006). "Low-calorie Sweeteners and Other Sugar Substitutes: A Review of the Safety Issues". Comprehensive Reviews in Food Science and Food Safety. 5 (2): 35–47. doi:10.1111/j.1541-4337.2006.tb00081.x. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  10. http://ec.europa.eu/food/fs/sc/scf/out52_en.pdf
  11. Liang Y (1987). "The effect of artificial sweetener on insulin secretion. 1. The effect of acesulfame K on insulin secretion in the rat (studies in vivo)". Horm Metab Res. 19 (6): 233–238. doi:10.1055/s-2007-1011788. PMID 2887500. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)
  12. "Toxicity studies of acesulfame potassium" (PDF). National institutes of health. Retrieved 2009-04-01.
  13. Public Health Service. "Toxicity Studies of Acesulfame Potassium" (PDF). Retrieved 30 March 2008.
  14. Soffritti, Morando. "Acesulfame Potassium: Soffritti Responds". Retrieved 30 March 2008.
  15. Karstadt, Myra L. "Testing Needed for Acesulfame Potassium, an Artificial Sweetener". Retrieved 30 March 2008.
  16. British Pharmacopoeia Commission Secretariat (2009). "Index, BP 2009" (PDF). Retrieved 4 February 2010. {{cite web}}: Cite has empty unknown parameter: |coauthors= (help)

External links

E numbers 950–969
Categories:
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