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Acesulfame potassium

From Wikipedia, the free encyclopedia
Calorie-free sugar substitute

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-1,2λ6,3-oxathiazin-4-olate
Other names
  • Acesulfame K
  • Ace K
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard100.054.269Edit this at Wikidata
EC Number
  • 259-715-3
E numberE950(glazing agents, ...)
UNII
  • InChI=1S/C4H5NO4S.K/c1-3-2-4(6)5-10(7,8)9-3;/h2H,1H3,(H,5,6);/q;+1/p-1 ☒N
    Key: WBZFUFAFFUEMEI-UHFFFAOYSA-M ☒N
  • InChI=1/C4H5NO4S.K/c1-3-2-4(6)5-10(7,8)9-3;/h2H,1H3,(H,5,6);/q;+1/p-1
    Key: WBZFUFAFFUEMEI-REWHXWOFAT
  • [K+].C\C1=C\C(=O)[N-]S(=O)(=O)O1
Properties
C4H4KNO4S
Molar mass201.242
Appearancewhite crystalline powder
Density1.81 g/cm3
Melting point225 °C (437 °F; 498 K)
270 g/L at 20 °C
Hazards
NFPA 704 (fire diamond)
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Acesulfame potassium (UK:/æsɪˈsʌlfm/,[1]US:/ˌsˈsʌlfm/AY-see-SUL-faym[2] or/ˌæsəˈsʌlfm/[1]), also known asacesulfame K orAce K, is a syntheticcalorie-freesugar substitute (artificial sweetener) often marketed under the trade namesSunett andSweet One. In the European Union, it is known under theE number (additive code)E950.[3] It was discovered accidentally in 1967 by German chemist Karl Clauss atHoechst AG (nowNutrinova).[4] 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 formulaC
4
H
4
KNO
4
S
and a molecular weight of 201.24 g/mol.[5]

Properties

[edit]

Acesulfame K is 200 times sweeter thansucrose (common sugar), as sweet asaspartame, about two-thirds as sweet assaccharin, and one-third as sweet assucralose. Like saccharin, it has a slightly bitteraftertaste, especially at high concentrations.Kraft Foods patented the use ofsodium ferulate to mask acesulfame's aftertaste.[6] Acesulfame K is often blended with other sweeteners (usually sucralose or aspartame). These blends are reputed to give a more sucrose-like taste whereby each sweetener masks the other's aftertaste, or exhibits asynergistic effect by which the blend is sweeter than its components.[7] Acesulfame potassium has a smaller particle size than sucrose, allowing for its mixtures with other sweeteners to be more uniform.[8]

Unlike aspartame, acesulfame K is stable under heat, even under moderately acidic or basic conditions, allowing it to be used as afood additive in baking, or in products that require a long shelf life. Although acesulfame potassium has a stable shelf life, it can eventually degrade toacetoacetamide, which is toxic in high doses.[9] Incarbonated 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,[10] especially chewable and liquid medications, where it can make the active ingredients more palatable. The acceptable daily intake of acesulfame potassium is listed as 15 mg/kg/day.[11]

Acesulfame potassium is widely used in the human diet and excreted by the kidneys. It thus has been used by researchers as a marker to estimate to what degree swimming pools are contaminated by urine.[12]

Other names for acesulfame K are potassium acesulfamate, potassium salt of 6-methyl-1,2,3-oxothiazin-4(3H)-one-2,3-dioxide, and potassium 6-methyl-1,2,3-oxathiazine-4(3H)-one-3-ate-2,2-dioxide.

Effect on body weight

[edit]

Acesulfame potassium provides a sweet taste with no caloric value. There is no high-quality evidence that using acesulfame potassium as a sweetener affects body weight orbody mass index (BMI).[13][14][15]

Discovery

[edit]

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.[16][17] After accidentally dipping his fingers into the chemicals with which he was working, Clauss licked them to pick up a piece of paper.[18] Clauss is the inventor listed on a United States patent issued in 1975 to the assignee Hoechst Aktiengesellschaft for one process of manufacturing acesulfame potassium.[19] Subsequent research showed a number of compounds with the same basic ring structure had different 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 theWorld Health Organization in 1978.[16] Acesulfame potassium first received approval for table top use in the United States in 1988.[11]

Safety

[edit]

The United StatesFood and Drug Administration (FDA) approved its general use as a safefood additive in 1988,[20] and maintains that safety assessment, as of 2023.[21] In a 2000 scientific review, theEuropean Food Safety Authority determined that acesulfame K is safe in typical consumption amounts, and does not increase the risk of diseases.[22]

Other sources

[edit]

References

[edit]
  1. ^ab"acesulfame".Oxford English Dictionary. OED. Retrieved24 July 2022.
  2. ^"acesulfame–K".Merriam-Webster.Archived from the original on 10 March 2017. Retrieved31 January 2017.
  3. ^"Current EU approved additives and their E Numbers". UK: Food Standards Agency. 2012-03-14.Archived from the original on 2013-08-21. Retrieved2012-08-07.
  4. ^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.
  5. ^Ager, D. J., Pantaleone, D. P., Henderson, S. A., Katritzky, A. R., Prakash, I., Walters, D. E. (1998)."Commercial, Synthetic Nonnutritive Sweeteners"(PDF).Angewandte Chemie International Edition.37 (13–14):1802–1817.doi:10.1002/(SICI)1521-3773(19980803)37:13/14<1802::AID-ANIE1802>3.0.CO;2-9. Archived fromthe original(PDF) on 2008-09-10.
  6. ^United States Patent 5,336,513 (expired in 2006)
  7. ^Deis RC (November 2006)."Customizing Sweetness Profiles"(PDF). Food Product Design. Archived fromthe original(PDF) on 11 August 2014. Retrieved16 May 2018.
  8. ^Mullarney, M.; Hancock, B.; Carlson, G.; Ladipo, D.; Langdon, B. "The powder flow and compact mechanical properties of sucrose and three high-intensity sweeteners used in chewable tablets".Int. J. Pharm. 2003, 257, 227–236.
  9. ^Findikli, Z.; Zeynep, F.; Sifa, T. Determination of the effects of some artificial sweeteners on human peripheral lymphocytes using the comet assay.Journal of toxicology and environmental health sciences 2014, 6, 147–153.
  10. ^"Home – WHO – Prequalification of Medicines Programme". Retrieved2 March 2017.
  11. ^abWhitehouse, C.; Boullata, J.; McCauley, L. "The potential toxicity of artificial sweeteners".AAOHN J. 2008, 56, 251–259, quiz 260.
  12. ^Erika Engelhaupt (March 1, 2017)."Just How Much Pee Is In That Pool?". NPR.Archived from the original on March 1, 2017. RetrievedMarch 2, 2017.
  13. ^Miller PE, Perez V (September 2014)."Low-calorie sweeteners and body weight and composition: a meta-analysis of randomized controlled trials and prospective cohort studies".The American Journal of Clinical Nutrition.100 (3):765–777.doi:10.3945/ajcn.113.082826.PMC 4135487.PMID 24944060.
  14. ^Azad MB, Abou-Setta AM, Chauhan BF, Rabbani R, Lys J, Copstein L, Mann A, Jeyaraman MM, Reid AE, Fiander M, MacKay DS, McGavock J, Wicklow B, Zarychanski R (July 2017)."Nonnutritive sweeteners and cardiometabolic health: a systematic review and meta-analysis of randomized controlled trials and prospective cohort studies".CMAJ.189 (28):E929 –E939.doi:10.1503/cmaj.161390.PMC 5515645.PMID 28716847.
  15. ^Rogers PJ, Hogenkamp PS, de Graaf C, Higgs S, Lluch A, Ness AR, Penfold C, Perry R, Putz P, Yeomans MR, Mela DJ (September 2015)."Does low-energy sweetener consumption affect energy intake and body weight? A systematic review, including meta-analyses, of the evidence from human and animal studies".International Journal of Obesity.40 (3):381–94.doi:10.1038/ijo.2015.177.PMC 4786736.PMID 26365102.
  16. ^abO'Brien-Nabors, L. (2001).Alternative Sweeteners. New York, NY: Marcel Dekker. p. 13.ISBN 978-0-8247-0437-7.
  17. ^Williams, R. J., Goldberg, I. (1991).Biotechnology and Food Ingredients. New York: Van Nostrand Reinhold.ISBN 978-0-442-00272-5.
  18. ^Newton, D. E. (2007).Food Chemistry (New Chemistry). New York: Infobase Publishing. p. 69.ISBN 978-0-8160-5277-6.Archived from the original on 2016-03-05. Retrieved2017-09-08.
  19. ^US 3917589, Clauss, K., "Process for the manufacture of 6-methyl-3,4-dihydro-1,2,3-oxathiazine-4-one-2,2-dioxide", issued 1975 
  20. ^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.
  21. ^"Aspartame and Other Sweeteners in Food". US Food and Drug Administration. 30 May 2023. Retrieved30 June 2023.
  22. ^Scientific Committee on Food (2000)."Opinion - Re-evaluation of acesulfame K with reference to the previous SCF opinion of 1991"(PDF).SCF/CS/ADD/EDUL/194 final. EU Commission. Archived fromthe original(PDF) on 2008-09-10. Retrieved2007-10-04.

External links

[edit]
Wikimedia Commons has media related toAcesulfame potassium.
E numbers 950–969


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