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Acesulfame potassium

January 01, 1970

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] 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.[5]

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 Y
3D model (JSmol)
  • Interactive image
ChEMBL
  • ChEMBL1351474 N
ChemSpider
  • 55940 N
ECHA InfoCard 100.054.269
EC Number
  • 259-715-3
E number E950 (glazing agents, ...)
  • 23683747
UNII
  • 23OV73Q5G9 Y
  • DTXSID1030606
  • 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 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 (fire diamond)
Health 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).
N verify (what is YN ?)

Properties edit

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 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 or body 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 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.[16] Acesulfame potassium first received approval for table top use in the United States in 1988.[11]

Safety edit

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]

Environment Canada tested[when?] 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.[23]

References edit

  1. ^ a b "acesulfame". Oxford English Dictionary. OED. Retrieved 24 July 2022.
  2. ^ "acesulfame–K". Merriam-Webster. 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. 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). (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. ^ (expired in 2006)
  7. ^ Deis RC (November 2006). (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. ^ a b 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. 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. ^ a b 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. 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). (PDF). SCF/CS/ADD/EDUL/194 final. EU Commission. Archived from the original (PDF) on 2008-09-10. Retrieved 2007-10-04.
  23. ^ "Major Canadian river contains artificial sweeteners". Waterloo News. University of Waterloo. December 13, 2013. from the original on October 21, 2014. Retrieved October 17, 2014.

External links edit

 
Wikimedia Commons has media related to Acesulfame potassium.
  • Joint FAO/WHO Expert Committee on Food Additives evaluation monograph of Acesulfame Potassium 2011-09-16 at the Wayback Machine
  • FDA approval of Acesulfame Potassium as a General Purpose Sweetener in Food
  • Elmhurst College, Illinois Virtual ChemBook
  • Discovery News

January 01, 1970
acesulfame, potassium, faym, also, known, acesulfame, symbol, potassium, synthetic, calorie, free, sugar, substitute, artificial, sweetener, often, marketed, under, trade, names, sunett, sweet, european, union, known, under, number, additive, code, e950, disco. Acesulfame potassium UK ae s ɪ ˈ s ʌ l f eɪ m 1 US ˌ eɪ s iː ˈ s ʌ l f eɪ m AY see SUL faym 2 or ˌ ae s e ˈ s ʌ l f eɪ m 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 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 C4 H4 KNO4 S and a molecular weight of 201 24 g mol 5 Acesulfame potassium Names IUPAC name Potassium 6 methyl 2 2 dioxo 2H 1 2l6 3 oxathiazin 4 olate Other names Acesulfame KAce K Identifiers CAS Number 55589 62 3 Y 3D model JSmol Interactive image ChEMBL ChEMBL1351474 N ChemSpider 55940 N ECHA InfoCard 100 054 269 EC Number 259 715 3 E number E950 glazing agents PubChem CID 23683747 UNII 23OV73Q5G9 Y CompTox Dashboard EPA DTXSID1030606 InChI InChI 1S C4H5NO4S K c1 3 2 4 6 5 10 7 8 9 3 h2H 1H3 H 5 6 q 1 p 1 NKey WBZFUFAFFUEMEI UHFFFAOYSA M NInChI 1 C4H5NO4S K c1 3 2 4 6 5 10 7 8 9 3 h2H 1H3 H 5 6 q 1 p 1Key WBZFUFAFFUEMEI REWHXWOFAT SMILES K C C1 C C O N S O O O1 Properties Chemical formula C 4H 4K N O 4S Molar mass 201 242 Appearance white crystalline powder Density 1 81 g cm3 Melting point 225 C 437 F 498 K Solubility in water 270 g L at 20 C Hazards NFPA 704 fire diamond 110 Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Contents 1 Properties 2 Effect on body weight 3 Discovery 4 Safety 5 References 6 External linksProperties editAcesulfame 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 editAcesulfame 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 editAcesulfame 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 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 16 Acesulfame potassium first received approval for table top use in the United States in 1988 11 Safety editThe 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 Environment Canada tested when 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 23 References edit a b acesulfame Oxford English Dictionary OED Retrieved 24 July 2022 acesulfame K Merriam Webster Archived from the original on 10 March 2017 Retrieved 31 January 2017 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 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 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 lt 1802 AID ANIE1802 gt 3 0 CO 2 9 Archived from the original PDF on 2008 09 10 United States Patent 5 336 513 expired in 2006 Deis RC November 2006 Customizing Sweetness Profiles PDF Food Product Design Archived from the original PDF on 11 August 2014 Retrieved 16 May 2018 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 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 Home WHO Prequalification of Medicines Programme Retrieved 2 March 2017 a b Whitehouse C Boullata J McCauley L The potential toxicity of artificial sweeteners AAOHN J 2008 56 251 259 quiz 260 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 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 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 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 a b O Brien Nabors L 2001 Alternative Sweeteners New York NY Marcel Dekker p 13 ISBN 978 0 8247 0437 7 Williams R J Goldberg I 1991 Biotechnology and Food Ingredients New York Van Nostrand Reinhold ISBN 978 0 442 00272 5 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 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 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 Aspartame and Other Sweeteners in Food US Food and Drug Administration 30 May 2023 Retrieved 30 June 2023 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 Major Canadian river contains artificial sweeteners Waterloo News University of Waterloo December 13 2013 Archived from the original on October 21 2014 Retrieved October 17 2014 External links edit nbsp Wikimedia Commons has media related to Acesulfame potassium Joint FAO WHO Expert Committee on Food Additives evaluation monograph of Acesulfame Potassium Archived 2011 09 16 at the Wayback Machine FDA approval of Acesulfame Potassium FDA approval of Acesulfame Potassium as a General Purpose Sweetener in Food Elmhurst College Illinois Virtual ChemBook Acesulfame K Discovery News Sweeteners Linger in Groundwater Retrieved from https en wikipedia org w index php title Acesulfame potassium amp oldid 1224590730, wikipedia, wiki, book, books, library,

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