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
55589-62-3 YesY
3D model (Jmol) Interactive image
ChEMBL ChEMBL1351474 N
ChemSpider 55940 N
ECHA InfoCard 100.054.269
EC Number 259-715-3
E number E950 (glazing agents, ...)
PubChem 23683747
UNII 23OV73Q5G9 YesY
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 oil Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special 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).
N verify (what is YesYN ?)
Infobox references

Acesulfame potassium (ace-SUHL-faym), also known as acesulfame K (K is the symbol for potassium) or Ace K, is a calorie-free sugar substitute (artificial sweetener), and marketed under the trade names Sunett and Sweet One. In the European Union, it is known under the E number (additive code) E950.[1] It was discovered accidentally in 1967 by German chemist Karl Clauss at Hoechst AG (now Nutrinova).[2] 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.[3]

Properties

Acesulfame K is 200 times sweeter than sucrose (common sugar), as sweet as aspartame, about 2/3 as sweet as saccharin, and 1/3 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.[4] 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. Acesulfame potassium has a smaller particle size than sucrose, allowing for its mixtures with other sweeteners to be more uniform.[5]

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.[6] 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,[7] 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.[8]

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.[9] 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.[9]

Acesulfame potassium is one of the non-nutritive sweeteners that aids patients with type 1 diabetes. It provides a super 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 thus increasing the risk of type 2 diabetes.[10]

Through a Maximal Electroshock Seizure test, non-nutritive sweeteners including acesulfame potassium were labeled as anticonvulsants.[11] This means that there is an association between the structure of the receptor that triggers the sweet sensation and the structure of the molecular targets of antiepileptic drugs.[11] It was also discovered that these non-nutritive sweeteners’ anticonvulsant activity is caused by modulation of brain mGlu.[11]

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.

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.[12][13] After accidentally dipping his fingers into the chemicals with which he was working, Clauss licked them to pick up a piece of paper.[14] 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.[15] 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.[12] Acesulfame potassium first received approval for table top use in the United States in 1988.[8]

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,[16] although these claims have been dismissed by the FDA[17] and equivalent authorities in the European Union.[18]

As for potential negative effects, when injected directly in very large doses (the equivalent of 10 g for an average sized human male), acesulfame K has been shown to stimulate dose-dependent insulin secretion in rats, though no hyperglycemia was observed.[19]

One rodent study showed no increased incidence of tumors in response to administration of acesulfame K.[20] 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 soft drinks every day). No sign indicated these (or lower) levels of acesulfame K increased the rats' risk of cancer or other neoplasms. However, a similar study conducted with p53 haploinsufficient mice showed signs of carcinogenicity in males but not females.[20] Further food safety research has been recommended.[16][21] Acesulfame K did not show any DNA-damaging properties.[22]

Research suggests acesulfame K may affect prenatal development. One study appeared to show acesulfame K is ingested by mice through their mothers' amniotic fluid or breast milk, and this influences the adult mouse's sweet preference.[23]

Additional research on the effects of acesulfame K on mice revealed chronic use over a period of 40 weeks resulted in a moderate but limited effect on neurometabolic function, and impaired cognitive memory functions. The authors proposed that this was caused by metabolically induced suppression of the T1r3 subunit of the taste receptor in the hippocampus.[24]

Environment Canada tested the water from the Grand River at 23 sites between its headwaters and where it dumps into Lake Erie. The results suggest the artificial sweetener acesulfame is the best at evading wastewater treatment, and it appears in far higher concentrations than saccharin or sucralose at the various test sites.[25]

In studies with animals, those animals who were exposed to low calorie sweeteners including acesulfame potassium have experienced some negative conditions including increased food consumption and weight gain, a greater percent of body fat, an increase in fasting glucose, a decrease in post-prandial thermogenesis, and a lower GLP-1 release during glucose tolerance testing.[26]

Compendial status

References

  1. ↑ "Current EU approved additives and their E Numbers". UK: Food Standards Agency. 2012-03-14.
  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. ↑ 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.
  4. ↑ United States Patent 5,336,513 (expired in 2006)
  5. ↑ 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.
  6. ↑ 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.
  7. ↑ http://www.who.int/prequal/trainingresources/pq_pres/TrainingZA-April07/Excipients.ppt
  8. 1 2 Whitehouse, C.; Boullata, J.; McCauley, L. The potential toxicity of artificial sweeteners. AAOHN J. 2008, 56, 251-9 quiz 260.
  9. 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.
  10. ↑ 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
  11. 1 2 3 Talevi, Alan; Enrique, Andrea V.; Bruno-Blanch, Luis E. Anticonvulsant activity of artificial sweeteners: A structural link between sweet-taste receptor T1R3 and brain glutamate receptors. 2012, 22, 12, 4072-4073, 4074
  12. 1 2 O'Brien-Nabors, L. (2001). Alternative Sweeteners. New York, NY: Marcel Dekker. p. 13. ISBN 0-8247-0437-1.
  13. ↑ Williams, R. J.; Goldberg, I. (1991). Biotechnology and Food Ingredients. New York: Van Nostrand Reinhold. ISBN 0-442-00272-6.
  14. ↑ Newton, D. E. (2007). Food Chemistry (New Chemistry). New York: Infobase Publishing. p. 69. ISBN 0-8160-5277-8.
  15. ↑ 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.
  16. 1 2 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 1570055Freely accessible. PMID 16966071.
  17. ↑ 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.
  18. ↑ 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.
  19. ↑ Liang, Y.; Steinbach, G.; Maier, V.; Pfeiffer, E. F. (1987). "The Effect of Artificial Sweetener on Insulin Secretion. 1. The Effect of Acesulfame K on Insulin Secretion in the Rat (Studies in Vivo)". Hormone and Metabolic Research. 19 (6): 233–238. doi:10.1055/s-2007-1011788. PMID 2887500.
  20. 1 2 National Toxicology Program (2005). "Toxicity Studies of Acesulfame Potassium (CAS No. 55589-62-3) in FVB/N-TgN(v-Ha-ras)Led (Tg.AC) Hemizygous Mice and Carcinogenicity Studies of Acesulfame Potassium in B6.129-Trp53tm1Brd (N5) Haploinsufficient Mice (Feed Studies)" (PDF). Genetically Modified Model Report. National Institutes of Health. 2005 (NTP GMM-2): 1–113. PMID 18784762. NIH Publication No. 06-4460.
  21. ↑ Soffritti, M. (2006). "Acesulfame Potassium: Soffritti Responds" (PDF). Environmental Health Perspectives. 114 (9): A516–A517. doi:10.1289/ehp.114-a516b. PMC 1570058Freely accessible.
  22. ↑ Weihrauch MR, Diehl V (2004). "Artificial sweeteners—do they bear a carcinogenic risk?". Ann Oncol. 15 (10): 1460–5. doi:10.1093/annonc/mdh256. PMID 15367404.
  23. ↑ Zhang, G. H.; Chen, M. L.; Liu, S. S.; Zhan, Y. H.; Quan, Y.; Qin, Y. M.; Deng, S. P. (2011). "Effects of Mother's Dietary Exposure to Acesulfame-K in Pregnancy or Lactation on the Adult Offspring's Sweet Preference". Chemical Senses. 36 (9): 763–770. doi:10.1093/chemse/bjr050. PMID 21653241.
  24. ↑ Cong W-n; Wang R; Cai H; Daimon CM; Scheibye-Knudsen M; et al. (2013). "Long-Term Artificial Sweetener Acesulfame Potassium Treatment Alters Neurometabolic Functions in C57BL/6J Mice". PLoS ONE. 8 (8): e70257. doi:10.1371/journal.pone.0070257. PMC 3737213Freely accessible. PMID 23950916.
  25. ↑ "Major Canadian river contains artificial sweeteners". Waterloo News. University of Waterloo. December 13, 2013.
  26. ↑ Fowler, S. P. (2016). "Low-calorie sweetener use and energy balance: Results from experimental studies in animals, and large-scale prospective studies in humans". Physiology & Behavior. 164 (Pt B): 517–23. doi:10.1016/j.physbeh.2016.04.047. PMC 5045440Freely accessible. PMID 27129676.
  27. ↑ British Pharmacopoeia Commission Secretariat (2009). "Index, BP 2009" (PDF). Archived from the original (PDF) on 2009-04-11.

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