SWEETENERS

Carbohydrate MiniTopics Carbohydrates  Elmhurst College
Sweet Receptor Site Saccharin Sucralose  Chemistry Department
Aspartame Cyclamate Acesulfame-K  Virtual ChemBook

Cyclamate

Introduction:

Cyclamate: Michael Sveda, while a graduate student at the University of Illinois, discovered cyclamate by smoking a cigarette. While working on the synthesis of anti-pyretic (anti-fever) drugs in the laboratory in 1937, he put his cigarette down on the lab bench. When he put it back in his mouth, he discovered the sweet taste of cyclamate (unsanitary lab technique).

Cyclamate was initially marketed as tablets that were recommended for use as a tabletop sweetener for diabetics. In 1958, cyclamates were classified as GRAS (Generally Recognized as Safe). A mixture of cyclamate and saccharin, which had been found to have synergistic sweetening properties and improved taste, was subsequently marketed for use in special dietary foods. In the 1950's diet drinks were introduced using a cyclamate/saccharin blend. The market grew rapidly and soon accounted for about 30% of the soft drink sales.

In 1969, the result of a chronic toxicity study with a mixture of cyclamate and saccharin was interpreted as implicating cyclamate as a bladder carcinogen in rats. Cyclamate was removed from GRAS status and eventually in 1970 banned in the United States from use in foods, beverages and drugs, and is still currently banned. However, many other countries did not act on this incomplete data, and cyclamate continued to be used as a sweetener in those countries. Today over 55 countries have approved the use of cyclamate.

Adapted from: Cyclamates

Cyclamate - Chime in new window

 

 

Sweetness Receptor Site:

Note: The model receptor site is this author's conception and is based only very loosely on theory and geometry of the molecules. It is only useful for students' initial conceptions of the fit of a molecule into a receptor site.

Area (AH+): This area has hydrogens available to hydrogen bond to oxygen that is part of the sulfur group.

Area (B -): This area has a partially negative oxygen available to hydrogen bond to the partially positive hydrogen of the amine group.

Area (X): This area is more or less perpendicular to the other two areas interacts through hydrophobic or non-polar properties to the non-polar the cyclohexane ring on the cyclamate molecule.