Sodium cyclamate

Sodium cyclamate

Names
IUPAC name sodium N-cyclohexylsulfamate
Identifiers
CAS Number	139-05-9 N
ChEMBL	ChEMBL273977 Y
ChemSpider	8421 Y
Jmol 3D model	Interactive image
PubChem	8751
UNII	1I6F42RME1 N
InChI InChI=1S/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 Y Key: UDIPTWFVPPPURJ-UHFFFAOYSA-M Y 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 Key: UDIPTWFVPPPURJ-REWHXWOFAV
SMILES [Na+].O=S([O-])(=O)NC1CCCCC1
Properties
Chemical formula	C6H12NNaO3S
Molar mass	201.22 g·mol−1
Vapor pressure	{{{value}}}
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 ?)
Infobox references

Sodium cyclamate (sweetener code 952) 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. It is less expensive than most sweeteners, including sucralose, and is stable under heating.

Chemistry

Cyclamate is the sodium or calcium salt of cyclamic acid (cyclohexanesulfamic acid), which itself is prepared by the sulfonation of cyclohexylamine. This can be accomplished by reacting cyclohexylamine with either sulfamic acid or sulfur trioxide.

History

Funny Face drink mix packet from 1970-71 advertising "No Cyclamate - Just Add Sugar"

Cyclamate was discovered in 1937 at the University of Illinois by graduate student Michael Sveda. Sveda was working in the lab on the synthesis of anti-fever medication. 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.

The patent for cyclamate was purchased by DuPont but 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 the United States in 1958, it was designated GRAS (Generally Recognized as Safe). 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.

Controversy developed when, 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 to increase the incidence of bladder cancer in rats. The released study was showing that eight out of 240 rats fed a mixture of saccharin and cyclamates, at levels of humans ingesting 350 cans of diet soda per day, developed bladder tumors.

Sales continue to expand, and in 1969 there were $1 billion in annual sales of cyclamate, which increased pressure from public safety watchdogs to restrict the use of cyclamate. In October 1969, Department of Health, Education & Welfare Secretary Robert Finch bypassed the Commissioner Herbert L. Ley, Jr. of the Food and Drug Administration and 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 Food and Drug Administration under a new FDA commissioner banned cyclamate completely from all food and drug products in the United States.

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. Abbott Labs, together with the Calorie Control Council (a political 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, cyclamate remains banned from food products in the United States. The petition is now held in abeyance, though not actively considered. It is unclear whether this is at the request of Abbott Labs or because the petition is considered to be insufficient by the FDA.

Food contamination

In Taipei, Taiwan, a city health survey in 2010 found nearly 30% of tested dried fruit products failed a health standards test, most having excessive amounts of cyclamate, some at levels 20 times higher than the legal limit.

Legal status

Cyclamate is approved as a sweetener in over 55 countries.

In the late 1960s cyclamate was banned in the United Kingdom but was approved after being re-evaluated by the European Union in 1996.

In the Philippines cyclamate was once banned, however in 2013 the Philippine Food and Drug Administration lifted the ban and it was declared safe for Philippine consumption.

Cyclamate is currently banned in the United States.

Brands

Sweeteners produced by Sweet'N Low and Sugar Twin for Canada contain cyclamate, though not those produced for the United States.

• Assugrin (Switzerland, Brazil)
• Chuker (Argentina) - Merisant Company 2, SARL
• Cologran
• Hermesetas
• Huxol (Germany) in liquid form
• Novasweet (Russia)
• Rio (Produced under license and authority of SweetLife AG Switzerland by SweetLife Ltd, China)
• Sucaryl
• Sugar Twin (Canada)
• Suitli (Bulgaria)
• Sweet N' Low (Canada)

External links

• European Commission Revised Opinion On Cyclamic Acid
• US FDA Petitions Currently Held in Abeyance
• List of other chemical and brand names for cyclamate
• A brief history of sweeteners, including the discovery of cyclamate