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

{{Use mdy dates|date=November 2018}}

| Name = Cyclamate <br /> {{small|(Sodium cyclamate)}}

| verifiedrevid = 477163337

| PIN = Sodium cyclohexylsulfamate

|Section1={{Chembox Identifiers

| InChIKey = UDIPTWFVPPPURJ-REWHXWOFAV

| CASNo_Ref = {{cascite|changed|??}}

| CASNo = 139-05-9

| PubChem = 8751

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| SMILES = [Na+].O=S([O-])(=O)NC1CCCCC1

| InChI = 1/C6H13NO3S.Na/c8-11(9,10)7-6-4-2-1-3-5-6;/h6-7H,1-5H2,(H,8,9,10);/q;+1/p-1

| UNII_Ref = {{fdacite|changed|FDA}}

| UNII = 1I6F42RME1

|Section2={{Chembox Properties

| C=6 | H=12 | N=1 | Na=1 | O=3 | S=1

| Appearance =

| Density =

| MeltingPt =

| BoilingPt =

| Solubility =

|Section3={{Chembox Hazards

| NFPA-H = 2

| NFPA-F = 1

| NFPA-R = 0

| MainHazards =

| FlashPt =

| AutoignitionPt =

'''Cyclamate''' is an [[artificial sweetener]]. It is 30–50 times sweeter than [[sucrose]] (table sugar), making it the least potent of the commercially used artificial sweeteners. It is often used with other artificial sweeteners, especially [[saccharin]]; the mixture of 10 parts cyclamate to 1 part saccharin is common and masks the off-tastes of both sweeteners.<ref>{{cite book|last1=Jim Smith, Lily Hong-Shum|title=Food Additives Data Book|date=April 15, 2008|publisher=John Wiley & Sons|page=960|url=https://books.google.com/books?id=7T8c12ifxaYC&pg=PA959|isbn=9781405172417}}</ref> It is less expensive than most sweeteners, including [[sucralose]], and is stable under heating. Safety concerns led to it being banned in a few countries, though the European Union considers it safe.

==Chemistry==

Cyclamate is the [[sodium]] or [[calcium]] [[Salt (chemistry)|salt]] of [[cyclamic acid]] (cyclohexanesulfamic acid), which itself is prepared by reacting freebase [[cyclohexylamine]] with either [[sulfamic acid]] or [[sulfur trioxide]].<ref>{{cite journal|last1=McKetta Jr|first1=John J.|title=Sweeteners, High Intensity|journal=Encyclopedia of Chemical Processing and Design|date=June 19, 1996|volume= 56|page=72|url=https://books.google.com/books?id=gb9UKnQEbeUC&pg=PA72|isbn=9780824726072}}</ref>

Prior to 1973, Abbott Laboratories produced sodium cyclamate (Sucaryl) by a mixture of ingredients including the addition of pure sodium (flakes or rods suspended in solvent) with cyclohexylamine, chilled and filtered through a high speed centrifugal separator, dried, granulated and micro-pulverised for powder or tablet usage.{{cn|date=December 2022}}

==History==

<!-- Deleted image removed: [[File:Funny Face drink mix 1969.jpg|thumb|right|Funny Face [[drink mix]] packet from 1970–71 advertising "No Cyclamate - Just Add Sugar"]] -->

Cyclamate was discovered in 1937 at the [[University of Illinois at Urbana–Champaign|University of Illinois]] by graduate student [[Michael Sveda]]. Sveda was working in the lab on the synthesis of an [[antipyretic]] drug. He put his [[cigarette]] down on the lab bench, and when he put it back in his mouth, he discovered the sweet taste of cyclamate.<ref>{{cite book |author=Packard, Vernal S. |title=Processed foods and the consumer: additives, labeling, standards, and nutrition |publisher=[[University of Minnesota Press]] |location=Minneapolis |year=1976 |pages=[https://archive.org/details/processedfoodsc00vern/page/332 332] |isbn=0-8166-0778-8 |url-access=registration |url=https://archive.org/details/processedfoodsc00vern/page/332 }}</ref><ref>{{cite web|url=https://www.nytimes.com/1999/08/21/business/michael-sveda-the-inventor-of-cyclamates-dies-at-87.html|title=Michael Sveda, the Inventor Of Cyclamates, Dies at 87|first=Leslie|last=Kaufman|date=August 21, 1999|work=New York Times|access-date=February 20, 2017|archive-date=September 12, 2017|archive-url=https://web.archive.org/web/20170912205427/http://www.nytimes.com/1999/08/21/business/michael-sveda-the-inventor-of-cyclamates-dies-at-87.html|url-status=live}}</ref>

The patent for cyclamate was purchased by [[DuPont]] and later sold to [[Abbott Laboratories]], which undertook the necessary studies and submitted a New Drug Application in 1950. Abbott intended to use cyclamate to mask the bitterness of certain drugs such as [[antibiotics]] and [[pentobarbital]]. In 1958, it was designated GRAS ([[Generally Recognized as Safe]]) by the United States [[Food and Drug Administration]]. Cyclamate was marketed in tablet form for use by diabetics as an alternative tabletop sweetener, as well as in a liquid form. As cyclamate is stable to heat, it was and is marketed as suitable for use in cooking and baking.{{cn|date=December 2022}}

In 1966, a study reported that some intestinal bacteria could desulfonate cyclamate to produce [[cyclohexylamine]], a compound suspected to have some chronic toxicity in animals. Further research resulted in a 1969 study that found the common 10:1 cyclamate–saccharin mixture increased the incidence of [[bladder cancer]] in [[rat]]s. The released study was showing that eight out of 240 rats fed a mixture of saccharin and cyclamates, at levels equivalent to humans ingesting 550 cans of diet soda per day, developed bladder tumors.<ref>{{Cite book|title=The Case against Sugar|last=Taubes|first=Gary|publisher=Portobello books|year=2017|isbn=9781846276378|location=London, England|pages=143–144}}</ref>

Sales continued to expand, and in 1969, annual sales of cyclamate had reached $1 billion, which increased pressure from public safety watchdogs to restrict the usage of cyclamate. In October 1969, [[United States Department of Health and Human Services|Department of Health, Education & Welfare]] Secretary [[Robert Finch (American politician)|Robert Finch]], bypassing [[Food and Drug Administration]] Commissioner [[Herbert L. Ley, Jr.]], removed the GRAS designation from cyclamate and banned its use in general-purpose foods, though it remained available for restricted use in dietary products with additional labeling; in October 1970, the FDA, under a new commissioner, banned cyclamate completely from all food and drug products in the United States.<ref name="The Search for Sweetness">{{cite journal|last1=Chedd|first1=Grahm|title=The Search for Sweetness|journal=New Scientist|date=May 9, 1974|volume=62|issue=897|page=299|url=https://books.google.com/books?id=zTFpyBr4WvgC&pg=PA299}}</ref>

Abbott Laboratories claimed that its own studies were unable to reproduce the 1969 study's results, and, in 1973, Abbott petitioned the FDA to lift the ban on cyclamate. This petition was eventually denied in 1980 by FDA Commissioner [[Jere Goyan]].<ref>{{cite web|url=https://www.fda.gov/downloads/food/ingredientspackaginglabeling/foodadditivesingredients/ucm404344.pdf|date=September 4, 1980|author=Goyan, Jere E., Commissioner of Food and Drugs.|title=Cyclamate, Commissioner's Decision, 45 FR 61474|quote="[...] approval of cyclamate for use as a sweetening agent in food and for technological purposes in food is denied."|pages=61474–61530|publisher=Office of the Federal Register|access-date=February 8, 2015|archive-date=April 12, 2015|archive-url=https://web.archive.org/web/20150412012308/http://www.fda.gov/downloads/Food/IngredientsPackagingLabeling/FoodAdditivesIngredients/UCM404344.pdf|url-status=live}}</ref> Abbott Labs, together with the [[Calorie Control Council]] (a political [[Lobbying|lobby]] representing the diet foods industry), filed a second petition in 1982. Although the FDA has stated that a review of all available evidence does not implicate cyclamate as a [[carcinogen]] in mice or rats,<ref>{{cite web |url=http://legacy.library.ucsf.edu/documentStore/c/y/b/cyb51c00/Scyb51c00.pdf|title=FDA Talk Paper, NAS Report on Cyclamate}}</ref> cyclamate remains banned from food products in the United States. The petition is now held in [[abeyance]], though not actively considered.<ref>{{cite web|url=https://www.fda.gov/Food/IngredientsPackagingLabeling/FoodAdditivesIngredients/ucm082418.htm|title=Petitions Currently Held in Abeyance|website=[[Food and Drug Administration]]|quote=FAP 2A3672 Cyclamate (cyclamic acid, calcium cyclamate, and sodium cyclamate)|access-date=February 8, 2015|archive-date=February 8, 2015|archive-url=https://web.archive.org/web/20150208073240/http://www.fda.gov/Food/IngredientsPackagingLabeling/FoodAdditivesIngredients/ucm082418.htm|url-status=live}}</ref> It is unclear whether this is at the request of Abbott Labs or because the petition is considered to be insufficient by the FDA.

In 2000, a paper was published describing the results of a 24-year-long experiment in which 16 monkeys were fed a normal diet and 21 monkeys were fed either 100 or 500&nbsp;mg/kg cyclamate per day; the higher dose corresponds to about 30 cans of a diet beverage. Two of the high-dosed monkeys and one of the lower-dosed monkeys were found to have malignant cancer, each with a different kind of cancer, and three benign tumors were found. The authors concluded that the study failed to demonstrate that cyclamate was carcinogenic because the cancers were all different and there was no way to link cyclamate to each of them.<ref name=one>{{cite journal|title=Artificial sweeteners—do they bear a carcinogenic risk?|vauthors=Weihrauch MR, Diehl V |journal=Ann Oncol|year=2004|volume=15|issue=10|pages=1460–5|pmid=15367404|doi=10.1093/annonc/mdh256|doi-access=free}}</ref> The substance did not show any DNA-damaging properties in DNA repair assays.<ref name=one/>

== Legal status ==

Cyclamate is approved as a sweetener in at least 130 countries.<ref>{{cite web|url=https://www.cyclamate.org/pdf/Cyclamate_worldwidestatus.pdf|title=Worldwide Status of Cyclamate|publisher=Calorie Control Council|access-date=23 November 2018|archive-date=February 4, 2022|archive-url=https://web.archive.org/web/20220204164415/https://www.cyclamate.org/pdf/Cyclamate_worldwidestatus.pdf|url-status=live}}</ref> In the late 1960s, cyclamate was banned in the United Kingdom; however, it was approved after being re-evaluated by the European Union in 1996.<ref>

{{cite book

| last= Ashurst

| first= Philip R.

| title= Chemistry and Technology of Soft Drinks and Fruit Juices

| date= April 15, 2008

| publisher= John Wiley & Sons

| page= 247

| isbn= 9781405141086

| url= https://books.google.com/books?id=KtlGWxu_KdMC&pg=PA247

}}

</ref>

In the [[Philippines]], cyclamate was banned until the [[Food and Drug Administration (Philippines)|Philippine Food and Drug Administration]] lifted the ban in 2013, declaring it safe for consumption.<ref>{{cite web|url=http://www.philstar.com/metro/2013/04/16/931145/fda-lifts-ban-magic-sugar|title=FDA lifts ban on 'magic sugar' - Philstar.com|website=philstar.com|access-date=April 16, 2013|archive-date=May 15, 2022|archive-url=https://web.archive.org/web/20220515070157/https://www.philstar.com/metro/2013/04/16/931145/fda-lifts-ban-magic-sugar|url-status=live}}</ref> Cyclamate remains banned in the United States and South Korea.<ref>{{cite web

| title= High-Intensity Sweeteners

| publisher= U.S. Food and Drug Administration

| date= May 19, 2014

| quote= "Are there any high-intensity sweeteners that are currently prohibited by FDA for use in the United States but are used in other countries? Yes. Cyclamates and its salts (such as calcium cyclamate, sodium cyclamate, magnesium cyclamate, and potassium cyclamate) are currently prohibited from use in the United States."

| url= https://www.fda.gov/food/ingredientspackaginglabeling/foodadditivesingredients/ucm397716.htm

| access-date= February 8, 2015

| archive-date= April 23, 2019

| archive-url= https://web.archive.org/web/20190423150420/https://www.fda.gov/Food/IngredientsPackagingLabeling/FoodAdditivesIngredients/ucm397716.htm

| url-status= live

}}</ref><ref>{{cite web

| title= Substances Added to Food (formerly Everything Added to Food in the United States (EAFUS)), Search Criteria = "cyclamate"

| publisher= U.S. Food and Drug Administration

| url= https://www.cfsanappsexternal.fda.gov/scripts/fdcc/?set=FoodSubstances&sort=Sortterm_ID&order=ASC&startrow=1&type=basic&search=cyclamate

| access-date= February 8, 2015

| archive-date= October 2, 2022

| archive-url= https://web.archive.org/web/20221002185508/https://www.cfsanappsexternal.fda.gov/scripts/fdcc/?set=FoodSubstances&sort=Sortterm_ID&order=ASC&startrow=1&type=basic&search=cyclamate

| url-status= live

}}</ref><ref>

{{cite book

| last= Newton

| first= David E

| title= Food Chemistry

| date= January 1, 2009

| pages= 73–77

| publisher= Infobase

| isbn= 9781438109756

| url= https://books.google.com/books?id=F29kaFKuJdMC&pg=PA73

}}

</ref><ref>{{Cite news|url=https://terms.naver.com/entry.nhn?docId=294190&cid=50314&categoryId=50314|script-title=ko:사이클라민산나트륨|access-date=August 23, 2018|language=ko}}</ref>

==Brands==

Sweeteners produced by [[Sweet'n Low]] and Sugar Twin<ref>{{cite web |url=http://www.sugartwin.com/ |title=Tastes like sugar |access-date=November 1, 2010 |archive-date=July 10, 2017 |archive-url=https://web.archive.org/web/20170710231553/http://www.sugartwin.com/ |url-status=dead }}</ref> for [[Canada]] contain cyclamate, though not those produced for the [[United States]].

* [[Assugrin]] (Switzerland, Brazil)<ref>[http://www.assugrin.ch/daten_f/maison.php Assugrin's website] {{Webarchive|url=https://web.archive.org/web/20070701171137/http://www.assugrin.ch/daten_f/maison.php |date=July 1, 2007 }} {{in lang|fr}}</ref>

* Cap Cangkir (Indonesia)

* Chuker (Argentina) – Merisant Company 2, SARL

* Cologran

* Huxol (Germany) in liquid form

* Hermesetas (Switzerland, incl. UK market) in mini tablet, granulated, and liquid form<ref>{{cite web|url=https://www.hermesetas.co.uk/products/hermesetas-granulated-2|title=Hermesetas}}</ref>

* Novasweet (Russia)<ref>{{cite web|url=http://novaprodukt.ru/|title=Новапродукт|website=novaprodukt.ru|access-date=November 27, 2011|archive-date=December 6, 2011|archive-url=https://web.archive.org/web/20111206011436/http://www.novaprodukt.ru/|url-status=live}}</ref>

* Rio (Produced under license and authority of SweetLife AG Switzerland by SweetLife Ltd, China)

* Sucaryl<ref>{{cite web|url=https://www.ponce-benzo.com/en/marcas/sucaryl/|title=Sucaryl|access-date=November 26, 2014|archive-date=June 29, 2015|archive-url=https://web.archive.org/web/20150629185515/https://www.ponce-benzo.com/en/marcas/sucaryl/|url-status=live}}</ref>

* Sugar Twin (Canada)<ref>{{cite web|url=https://sugartwin.ca/product/sachets/|title=SugarTwin - Artificial Sweeteners - Sugar Substitutes - Calorie Free|website=Sugar Twin|access-date=January 16, 2022|archive-date=January 16, 2022|archive-url=https://web.archive.org/web/20220116194735/https://sugartwin.ca/product/sachets/|url-status=live}}</ref>

* Suitli (Bulgaria)

* Sweet'n Low (Canada)

* Sugromax (New Zealand)<ref>{{cite web|url=https://www.sugromax.co.nz/|title=Sugromax :: Home|website=Sugromax|access-date=October 9, 2021|archive-date=October 9, 2021|archive-url=https://web.archive.org/web/20211009205045/https://www.sugromax.co.nz/|url-status=live}}</ref>

* El Dorra (Tunisia) <ref>{{cite web|title= Labo-arrazi|url= http://www.labo-arrazi.tn/index.php?idm=3&ids=5&idss=12|access-date= May 5, 2023|archive-date= November 27, 2022|archive-url= https://web.archive.org/web/20221127114417/http://www.labo-arrazi.tn/index.php?idm=3&ids=5&idss=12|url-status= live}}</ref>

==Notes and references==

{{Reflist|2}}

==External links==

{{Commonscat}}

* [http://ec.europa.eu/food/fs/sc/scf/out53_en.pdf European Commission Revised Opinion On Cyclamic Acid]

* [https://www.fda.gov/downloads/food/ingredientspackaginglabeling/foodadditivesingredients/ucm404344.pdf FDA Commissioner's Decision on Cyclamate, 45 FR 61474]

{{E number infobox 950-969}}

{{Consumer Food Safety}}

{{Food Substitutes}}

[[Category:Abbott Laboratories]]

[[Category:Sulfamates]]

[[Category:Sugar substitutes]]

[[Category:Sodium compounds|Cyclamate]]

[[Category:Cyclohexyl compounds]]

[[Category:Suspected carcinogens]]

[[Category:E-number additives]]