Acesulfame potassium

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Acesulfame potassium
Acesulfame potassium Structural Formula V1.svg
Acesulfame-k-ball-and-stick.png
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 InfoCard 100.054.269 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 259-715-3
E number E950 (glazing agents, ...)
PubChem CID
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 X mark.svgN
    Key: WBZFUFAFFUEMEI-UHFFFAOYSA-M X mark.svgN
  • 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 mass 201.242
Appearancewhite crystalline powder
Density 1.81 g/cm3
Melting point 225 °C (437 °F; 498 K)
270 g/L at 20 °C
Hazards
NFPA 704 (fire diamond)
NFPA 704.svgHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
1
0
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 ?)

Acesulfame potassium ( UK: /æsɪˈsʌlfeɪm/ , [1] US: /ˌeɪsiːˈsʌlfeɪm/ AY-see-SUL-faym [2] or /ˌæsəˈsʌlfeɪm/ [1] ), also known as acesulfame K (K is the symbol for potassium) or Ace K, is a synthetic calorie-free sugar substitute (artificial sweetener) often marketed under the trade names Sunett and Sweet One. In the European Union, it is known under the E number (additive code) E950. [3] It was discovered accidentally in 1967 by German chemist Karl Clauss at Hoechst AG (now Nutrinova). [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 formula C
4H
4KNO
4S and a molecular weight of 201.24 g/mol. [5]

Properties

Acesulfame K is 200 times sweeter than sucrose (common sugar), as sweet as aspartame, about two-thirds as sweet as saccharin, and one-third as sweet as sucralose. Like saccharin, it has a slightly bitter aftertaste, especially at high concentrations. Kraft Foods patented the use of sodium 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 a synergistic 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 a food additive in baking, or in products that require a long shelf life. Although acesulfame potassium has a stable shelf life, it can eventually degrade to acetoacetamide, which is toxic in high doses. [9] 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, [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

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 or body mass index (BMI). [13] [14] [15]

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. [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 the World Health Organization in 1978. [16] Acesulfame potassium first received approval for table top use in the United States in 1988. [11]

Safety

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

Related Research Articles

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Equal is an American brand of artificial sweetener containing aspartame, acesulfame potassium, dextrose and maltodextrin. It is marketed as a tabletop sweetener by Merisant, a global corporation which also previously owned the well-known NutraSweet brand when it was a subsidiary of Monsanto and which has headquarters in Chicago, Illinois, Switzerland, Mexico, and Singapore. In French Canada, Equal is known as "Égal".

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References

  1. 1 2 "acesulfame". Oxford English Dictionary. OED. Retrieved 24 July 2022.
  2. ↑ "acesulfame–K". Merriam-Webster. Archived from the original on 10 March 2017. Retrieved 31 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. Retrieved 2012-08-07.
  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 from the 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 from the original (PDF) on 11 August 2014. Retrieved 16 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" . Retrieved 2 March 2017.
  11. 1 2 Whitehouse, 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. Retrieved March 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. 1 2 O'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. Retrieved 2017-09-08.
  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. Retrieved 30 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 from the original (PDF) on 2008-09-10. Retrieved 2007-10-04.
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