Acesulfame potassium

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 InfoCard 100.054.269
EC Number 259-715-3
E number E950 (glazing agents, ...)
UNII
Properties
C4H4KNO4S
Molar mass 201.242
Appearance white crystalline powder
Density 1.81 g/cm3
Melting point 225 °C (437 °F; 498 K)
270 g/L at 20 °C
Hazards
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oilHealth code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentineReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogenSpecial hazards (white): no codeNFPA 704 four-colored diamond
1
1
0
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

Acesulfame potassium (/ˌeɪsiːˈsʌlfeɪm/ AY-see-SUL-faym[1]), also known as acesulfame K (K is the symbol for potassium) or Ace K, is a 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.[2] It was discovered accidentally in 1967 by German chemist Karl Clauss at Hoechst AG (now Nutrinova).[3] 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
4H
4KNO
4S and a molecular weight of 201.24 g/mol.[4]

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.[5] 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.[6] Acesulfame potassium has a smaller particle size than sucrose, allowing for its mixtures with other sweeteners to be more uniform.[7]

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.[8] 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,[9] 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.[10]

Acesulfame potassium as well as other sugar substituents were intercalated into some layered double hydroxide (LDH) hosts by ion exchange. Characterization tests have shown that there is complete intercalation of the anions into the LDH hosts. In acesulfame K, the absorption at 1290 cm−1 is found in the intercalated product at 1314 cm−1.[11] Since this absorption corresponds to the S-O double bond, it means that the bonds interact strongly with the metal hydroxide layers thus an orientation of the intercalated molecules is possible.[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.

Effectiveness for weight reduction

Acesulfame potassium provides a sweet taste without affecting glycaemic responses and without the high content of caloric sugars. Some studies, however, discovered that the consumption of non-nutritive sweeteners has led to weight gain because people over-ingest calories, thus increasing the risk of type 2 diabetes.[13]

A 2016 systematic review of published studies about the effects of artificially sweetened beverages on weight found that artificial sweetener industry-sponsored studies were significantly more likely to have favorable results than non-industry sponsored studies, and that all published studies that were funded by competitor industries reported unfavorable conclusions.[14]

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.[15][16] After accidentally dipping his fingers into the chemicals with which he was working, Clauss licked them to pick up a piece of paper.[17] 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.[18] Subsequent research showed 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.[15] Acesulfame potassium first received approval for table top use in the United States in 1988.[10]

Safety

As with other artificial sweeteners, concern exists over the safety of acesulfame potassium. However, the United States Food and Drug Administration (FDA) has approved its general use. Critics say acesulfame potassium has not been studied adequately and may be carcinogenic,[19] although these claims have been dismissed by the European Food Safety Authority[20] and FDA.[21]

Environment Canada tested the water from the Grand River at 23 sites between its headwaters and where it flows into Lake Erie. The results suggest that acesulfame appears in far higher concentrations than saccharin or sucralose at the various test sites.[22]

Compendial status

References

  1. ↑ "acesulfame–K". Merriam-Webster. Merriam-Webster. Retrieved 31 January 2017.
  2. ↑ "Current EU approved additives and their E Numbers". UK: Food Standards Agency. 2012-03-14.
  3. ↑ 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.
  4. ↑ 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.
  5. ↑ United States Patent 5,336,513 (expired in 2006)
  6. ↑ Deis RC (November 2006). "Customizing Sweetness Profiles" (PDF). Food Product Design. Retrieved 16 May 2018.
  7. ↑ 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.
  8. ↑ 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.
  9. ↑ "Home - WHO - Prequalification of Medicines Programme". Retrieved 2 March 2017.
  10. 1 2 Whitehouse, C.; Boullata, J.; McCauley, L. The potential toxicity of artificial sweeteners. AAOHN J. 2008, 56, 251-9 quiz 260.
  11. 1 2 Markland, Charles; Williams, Gareth R.; O'Hare, Dermot (2011). "The intercalation of flavouring compounds into layered double hydroxides". Journal of Materials Chemistry. 21 (44): 17896. doi:10.1039/C1JM13375F.
  12. ↑ Erika Engelhaupt (March 1, 2017). "Just How Much Pee Is In That Pool?". NPR. Retrieved March 2, 2017.
  13. ↑ Dewinter, Louise; Casteels, Kristina; Corthouts, Karen; Van de Kerckhove, Kristel; Van der Vaerent, Katrien; Vanmeerbeeck, Kelly; Matthys, Christophe. Dietary intake of non-nutritive sweeteners in type 1 diabetes mellitus children Food additives contaminants. Part A.Chemistry, analysis, control, exposure risk assessment, 2015, 33, 1, 1-8, Taylor Francis, ENGLAND
  14. ↑ Mandrioli, Daniele; Kearns, Cristin E.; Bero, Lisa A. (2016-09-08). "Relationship between Research Outcomes and Risk of Bias, Study Sponsorship, and Author Financial Conflicts of Interest in Reviews of the Effects of Artificially Sweetened Beverages on Weight Outcomes: A Systematic Review of Reviews". PLOS ONE. 11 (9): e0162198. doi:10.1371/journal.pone.0162198. ISSN 1932-6203.
  15. 1 2 O'Brien-Nabors, L. (2001). Alternative Sweeteners. New York, NY: Marcel Dekker. p. 13. ISBN 0-8247-0437-1.
  16. ↑ Williams, R. J.; Goldberg, I. (1991). Biotechnology and Food Ingredients. New York: Van Nostrand Reinhold. ISBN 0-442-00272-6.
  17. ↑ Newton, D. E. (2007). Food Chemistry (New Chemistry). New York: Infobase Publishing. p. 69. ISBN 0-8160-5277-8.
  18. ↑ Clauss, K. Process for the manufacture of 6-methyl-3,4-dihydro-1,2,3-oxathiazine-4-one-2,2-dioxide. US Patent 3917589, 1975.
  19. ↑ Karstadt, M. L. (2006). "Testing Needed for Acesulfame Potassium, an Artificial Sweetener" (PDF). Environmental Health Perspectives. 114 (9): A516, author reply A516–7. doi:10.1289/ehp.114-a516a. PMC 1570055. PMID 16966071.
  20. ↑ 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.
  21. ↑ 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.
  22. ↑ "Major Canadian river contains artificial sweeteners". Waterloo News. University of Waterloo. December 13, 2013.
  23. ↑ British Pharmacopoeia Commission Secretariat (2009). "Index, BP 2009" (PDF). Archived from the original (PDF) on 2009-04-11.
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