Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Acesulfame potassium: Difference between pages

{{Short description|Calorie-free sugar substitute}}

{{cs1 config|name-list-style=vanc}}

{{Chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 477238396

| ImageFile = Acesulfame potassium Structural Formula V1.svg

| IUPACName = Potassium 6-methyl-2,2-dioxo-2''H''-1,2''λ''⁶,3-oxathiazin-4-olate

| OtherNames = {{Unbulleted list|Acesulfame K|Ace K}}

|Section1={{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 55940

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 1351474

| InChI = 1/C4H5NO4S.K/c1-3-2-4(6)5-10(7,8)9-3;/h2H,1H3,(H,5,6);/q;+1/p-1

| InChIKey = WBZFUFAFFUEMEI-REWHXWOFAT

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C4H5NO4S.K/c1-3-2-4(6)5-10(7,8)9-3;/h2H,1H3,(H,5,6);/q;+1/p-1

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = WBZFUFAFFUEMEI-UHFFFAOYSA-M

| SMILES = [K+].C\C1=C\C(=O)[N-]S(=O)(=O)O1

|Section2={{Chembox Properties

| Formula =

| C=4 | H=4 | K=1 | N=1 | O=4 | S=1

|Section3={{Chembox Hazards

| NFPA-H = 1

| NFPA-F = 1

| NFPA-R = 0

| AutoignitionPt =

'''Acesulfame potassium''' ({{IPAc-en|uk|æ|s|ᵻ|ˈ|s|ʌ|l|f|eɪ|m}},<ref name="auto">{{cite encyclopedia |title=acesulfame |encyclopedia=Oxford English Dictionary |date= |year= |publisher= |location= |id=OED |url=https://www.oed.com/view/Entry/247745 |access-date=24 July 2022}}</ref> {{IPAc-en|us|ˌ|eɪ|s|iː|ˈ|s|ʌ|l|f|eɪ|m}} {{respell|AY|see|SUL|faym}}<ref>{{cite web|title=acesulfame–K|url=https://www.merriam-webster.com/dictionary/acesulfame%E2%80%93K|website=Merriam-Webster|access-date=31 January 2017|archive-url=https://web.archive.org/web/20170310220058/https://www.merriam-webster.com/dictionary/acesulfame%E2%80%93K|archive-date=10 March 2017|url-status=live}}</ref> or {{IPAc-en|ˌ|æ|s|ə|ˈ|s|ʌ||l|f|eɪ|m}}<ref name="auto"/>), also known as '''acesulfame K ''' ('''K''' is the [[chemical symbol|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'''.<ref>{{cite web | url = http://www.food.gov.uk/policy-advice/additivesbranch/enumberlist | title = Current EU approved additives and their E Numbers | publisher = Food Standards Agency | location = UK | date = 2012-03-14 | access-date = 2012-08-07 | archive-url = https://web.archive.org/web/20130821045312/http://food.gov.uk/policy-advice/additivesbranch/enumberlist | archive-date = 2013-08-21 | url-status = live }}</ref> It was discovered accidentally in 1967 by German chemist Karl Clauss at [[Hoechst AG]] (now [[Nutrinova]]).<ref>{{cite journal|author1=Clauss, K. |author2=Jensen, H. | title = Oxathiazinone Dioxides - A New Group of Sweetening Agents | journal = Angewandte Chemie International Edition | year = 1973 | volume = 12 | issue = 11 | pages = 869–876 | doi = 10.1002/anie.197308691 }}</ref> In chemical structure, acesulfame potassium is the potassium salt of 6-methyl-1,2,3-oxathiazine-4(3''H'')-one 2,2-dioxide. It is a white crystalline powder with molecular formula {{chem|C|4|H|4|KNO|4|S}} and a molecular weight of 201.24&nbsp;g/mol.<ref>{{cite journal|author1=Ager, D. J. |author2=Pantaleone, D. P. |author3=Henderson, S. A. |author4=Katritzky, A. R. |author5=Prakash, I. |author6=Walters, D. E. |title=Commercial, Synthetic Nonnutritive Sweeteners |journal=Angewandte Chemie International Edition |year=1998 |volume=37 |issue=13–14 |pages=1802–1817 |doi=10.1002/(SICI)1521-3773(19980803)37:13/14<1802::AID-ANIE1802>3.0.CO;2-9 |url=http://ufark12.chem.ufl.edu/Published_Papers/PDF/728.pdf |url-status=dead |archive-url=https://web.archive.org/web/20080910124009/http://ufark12.chem.ufl.edu/Published_Papers/PDF/728.pdf |archive-date=2008-09-10 }}</ref>

==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.<ref>[https://web.archive.org/web/20170430070157/http://patft.uspto.gov/netacgi/nph-Parser?patentnumber=5336513 United States Patent 5,336,513] (expired in 2006)</ref> 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 [[Synergy|synergistic]] effect by which the blend is sweeter than its components.<ref>{{cite web|author1=Deis RC|title=Customizing Sweetness Profiles|url=http://nfscfaculty.tamu.edu/talcott/courses/FSTC605/Food%20Product%20Design/Customizing%20Sweetness.pdf|publisher=Food Product Design|access-date=16 May 2018|date=November 2006|archive-url=https://web.archive.org/web/20140811002814/http://nfscfaculty.tamu.edu/talcott/courses/FSTC605/Food%20Product%20Design/Customizing%20Sweetness.pdf|archive-date=11 August 2014|url-status=dead}}</ref> Acesulfame potassium has a smaller particle size than sucrose, allowing for its mixtures with other sweeteners to be more uniform.<ref>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.</ref>

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.<ref>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.</ref> In [[Carbonation|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,<ref>{{cite web|url=https://www.who.int/prequal/trainingresources/pq_pres/TrainingZA-April07/Excipients.ppt|title=Home – WHO – Prequalification of Medicines Programme|access-date=2 March 2017}}</ref> 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&nbsp;mg/kg/day.<ref name="Whitehouse, C. 2008">Whitehouse, C.; Boullata, J.; McCauley, L. "The potential toxicity of artificial sweeteners". ''AAOHN J.'' 2008, 56, 251–259, quiz 260.</ref>

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.<ref name="npr2017">{{cite news |url=https://www.npr.org/sections/health-shots/2017/03/01/517785902/just-how-much-pee-is-in-that-pool |author=Erika Engelhaupt |title=Just How Much Pee Is In That Pool? |publisher=NPR |date=March 1, 2017 |access-date=March 2, 2017 |archive-url=https://web.archive.org/web/20170301203510/http://www.npr.org/sections/health-shots/2017/03/01/517785902/just-how-much-pee-is-in-that-pool |archive-date=March 1, 2017 |url-status=live }}</ref>

Other names for acesulfame K are potassium acesulfamate, potassium salt of 6-methyl-1,2,3-oxothiazin-4(3''H'')-one-2,3-dioxide, and potassium 6-methyl-1,2,3-oxathiazine-4(3''H'')-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).<ref name="Miller2014">{{cite journal | vauthors = Miller PE, Perez V | title = Low-calorie sweeteners and body weight and composition: a meta-analysis of randomized controlled trials and prospective cohort studies | journal = The American Journal of Clinical Nutrition | volume = 100 | issue = 3 | pages = 765–777 | date = September 2014 | pmid = 24944060 | doi = 10.3945/ajcn.113.082826 | pmc = 4135487 }}</ref><ref name=Az2017>{{cite journal | vauthors = 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 | title = Nonnutritive sweeteners and cardiometabolic health: a systematic review and meta-analysis of randomized controlled trials and prospective cohort studies | journal = CMAJ | volume = 189 | issue = 28 | pages = E929–E939 | date = July 2017 | pmid = 28716847 | pmc = 5515645 | doi = 10.1503/cmaj.161390 }}</ref><ref name="Rogers2015">{{cite journal | vauthors = Rogers PJ, Hogenkamp PS, de Graaf C, Higgs S, Lluch A, Ness AR, Penfold C, Perry R, Putz P, Yeomans MR, Mela DJ | title = 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 | journal = International Journal of Obesity | volume = 40 | issue = 3 | pages = 381–94 | date = September 2015 | doi = 10.1038/ijo.2015.177 | pmid = 26365102 | pmc = 4786736 }}</ref>

==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]].<ref name="isbn0-8247-0437-1">{{cite book | author = O'Brien-Nabors, L. | title = Alternative Sweeteners | publisher = Marcel Dekker | location = New York, NY | year = 2001 | page = 13 | isbn = 978-0-8247-0437-7 }}</ref><ref name="isbn0-442-00272-6">{{cite book |author1=Williams, R. J. |author2=Goldberg, I. | title = Biotechnology and Food Ingredients | publisher = Van Nostrand Reinhold | location = New York | year = 1991 | isbn = 978-0-442-00272-5 }}</ref> After accidentally dipping his fingers into the chemicals with which he was working, Clauss licked them to pick up a piece of paper.<ref name="isbn0-8160-5277-8">{{cite book | author = Newton, D. E. | title = Food Chemistry (New Chemistry) | publisher = Infobase Publishing | location = New York | year = 2007 | page = 69 | isbn = 978-0-8160-5277-6 | url = https://www.scribd.com/doc/50359642/Food-Chemistry#page=82 | access-date = 2017-09-08 | archive-url = https://web.archive.org/web/20160305104737/https://www.scribd.com/doc/50359642/Food-Chemistry#page=82 | archive-date = 2016-03-05 | url-status = live }}</ref> 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.<ref>{{cite patent|inventor=Clauss, K. |title=Process for the manufacture of 6-methyl-3,4-dihydro-1,2,3-oxathiazine-4-one-2,2-dioxide |country=US |number=3917589 |gdate=1975}}</ref> 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(3''H'')-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.<ref name="isbn0-8247-0437-1" /> Acesulfame potassium first received approval for table top use in the United States in 1988.<ref name="Whitehouse, C. 2008"/>

==Safety==

The [[Food and Drug Administration|United States Food and Drug Administration]] (FDA) approved its general use as a safe [[food additive]] in 1988,<ref name="Kroger_2006">{{cite journal |author1=Kroger, M. |author2=Meister, K. |author3=Kava, R. | title = Low-Calorie Sweeteners and Other Sugar Substitutes: A Review of the Safety Issues | journal = [[Comprehensive Reviews in Food Science and Food Safety]] | year = 2006 | volume = 5 | issue = 2 | pages = 35–47 | doi = 10.1111/j.1541-4337.2006.tb00081.x | doi-access = free }}</ref> and maintains that safety assessment, as of 2023.<ref name="fda5-23">{{cite web |title=Aspartame and Other Sweeteners in Food |url=https://www.fda.gov/food/food-additives-petitions/aspartame-and-other-sweeteners-food |publisher=US Food and Drug Administration |access-date=30 June 2023 |date=30 May 2023}}</ref> 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.<ref>{{cite web | url = http://ec.europa.eu/food/fs/sc/scf/out52_en.pdf | title = Opinion - Re-evaluation of acesulfame K with reference to the previous SCF opinion of 1991 | publisher = EU Commission | author = Scientific Committee on Food | work = SCF/CS/ADD/EDUL/194 final | year = 2000 | access-date = 2007-10-04 | archive-url = https://web.archive.org/web/20080910124007/http://ec.europa.eu/food/fs/sc/scf/out52_en.pdf | archive-date = 2008-09-10 | url-status = dead }}</ref>

[[Environment Canada]] tested the water from the [[Grand River (Ontario)|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.<ref>{{cite news | title = Major Canadian river contains artificial sweeteners | newspaper = Waterloo News | location = University of Waterloo | date = December 13, 2013 | url = https://uwaterloo.ca/news/news/major-canadian-river-contains-artificial-sweeteners | access-date = October 17, 2014 | archive-url = https://web.archive.org/web/20141021220129/https://uwaterloo.ca/news/news/major-canadian-river-contains-artificial-sweeteners | archive-date = October 21, 2014 | url-status = live }}</ref>

==References==

{{Reflist}}

==External links==

{{Commons category}}

*[http://www.fao.org/ag/agn/jecfa-additives/details.html?id=841 Joint FAO/WHO Expert Committee on Food Additives evaluation monograph of Acesulfame Potassium] {{Webarchive|url=https://web.archive.org/web/20110916033139/http://www.fao.org/ag/agn/jecfa-additives/details.html?id=841 |date=2011-09-16 }}

*[https://web.archive.org/web/20120225051955/http://edocket.access.gpo.gov/cfr_2001/aprqtr/21cfr172.800.htm FDA approval of Acesulfame Potassium]

*[http://edocket.access.gpo.gov/cfr_2004/aprqtr/pdf/21cfr172.755.pdf FDA approval of Acesulfame Potassium as a General Purpose Sweetener in Food]

* Elmhurst College, Illinois Virtual ChemBook [https://web.archive.org/web/20030826200357/http://www.elmhurst.edu/~chm/vchembook/549acesulfame.html Acesulfame K]

* Discovery News [https://web.archive.org/web/20090525083413/http://dsc.discovery.com/news/2009/05/22/artificial-sweetener.html Sweeteners Linger in Groundwater]

{{E number infobox 950-969}}

{{Consumer Food Safety}}

{{Food Substitutes}}

{{Authority control}}

[[Category:Excipients]]

[[Category:Food additives]]

[[Category:Oxathiazines]]

[[Category:Potassium compounds]]

[[Category:Sulfamates]]

[[Category:Sugar substitutes]]

[[Category:E-number additives]]