Cyclamates

Sodium cyclamate

Names
IUPAC name sodium N-cyclohexylsulfamate
Identifiers
CAS Number	139-05-9 N
3D model (Jmol)	Interactive image
ChemSpider	8421 Y
ECHA InfoCard	100.004.863
PubChem CID	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
Hazards
NFPA 704	1 2 0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (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.

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.

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 kerosene) with cyclohexylamine, chilled and filtered through a high speed centrifugal separator, dried, granulated and micro-pulverised for powder or tablet usage.

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 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.