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

Relative Sweetness Scale - Sucrose = 100  Compound  Rating  Sucrose  100  Fructose  140  High Fructose Corn Syrup  120-160  Glucose  70-80  Galactose  35  Maltose  30-50  Lactose  20

Sweetners - Introduction Introduction: Carbohydrates are an important dietary nutrienet which is mostly used to supply energy to the body, as well as, a carbon source for synthesis of other needed chemicals. In addition mono- and disaccharides are craved because of their sweetness. All carbohydrate sweeteners (sugar, evaporated cane juice, turbinado sugar, honey, high fructose corn syrup, maple syrup, juice concentrates) contain primarily sugars and do not provide significant amounts of vitamins and minerals. We value sugar and other natural sweeteners because they enhance taste and enjoyment of a wide variety of nutritious foods. USDA estimates that for 1997 about 67 pounds of sugar (cane and beet); 86 pounds of corn sweeteners; and 1 pound of other sweeteners (honey, maple syrup) per capita were delivered into the food supply. That adds up to a total carbohydrate sweetener availability of about 154 pounds per capita. Saccharides have varying degrees of sweetness on a relative scale as illustrated in the table on the left. Fructose is the sweetest, while lactose is only slightly sweet by comparison. Originally the needs of diabetics and more recently the soft drink industry has provided the stimulus in the search of other sweetners.

Relative Sweetness Scale - Sucrose = 1  Compound  Rating  Saccharin  300 X  Cyclamate  30 X  Aspartame  180 X  Acesulfame  200 X  Sucralose 600 X

Discovery of Non-Carbohydrate Sweetners: Saccharin was discovered in 1879 by Constantine Fahlberg, while working in the laboratory of Ira Remsen, quite by accident as were most other sweetners. While working in the lab, he spilled a chemical on his hand. Later while eating dinner, Fahlberg noticed a more sweetness in the bread he was eating. He traced the sweetness back to the chemical, later named saccharin, by tasting various residues on his hands and clothes (unsanitary conditions) and finally chemicals in the lab (not a safe lab practice). By 1907, saccharin was used as a replacement for sugar in foods for diabetics. Since it is not metabolized in the body for energy, saccharin is classified as a noncaloric sweetner. By the 1960s it was used on a massive scale in the "diet" soft drink industry.   Aspartame: In 1965, Jim Schlatter, a chemist at G.D. Searle was working on a on a project to discover new treatments for gastric ulcers. One of the steps in the research process was to make a dipeptide intermediate, aspartyl-phenylalanine methyl ester. He accidently and unknownly spilled some on his hand. Later he licked his finger as he reached for a piece of paper (unsanitary lab technique), and noticed the sweet taste. He and a friend decided to test some in coffee and confirmed the identify of the chemical with the sweet taste. The result was the sweetner, aspartame.   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).   Acesulfame was discovered by another chemist, Karl Clauss, in 1967. He noticed a sweet taste when he licked his finger to pick up a piece of paper (unsanitary lab technique).   Sucralose may have the strangest "accidental discovery" story. Tate & Lyle, a British sugar company, was looking for ways to use sucrose as a chemical intermediate. Halogenated sugars were being synthesized and tested. A foreign graduate student, Shashikant Phadnis, misunderstood a request for "testing" of a chlorinated sugar as a request for "tasting," leading to the discovery that many chlorinated sugars are sweet with potencies some hundreds or thousands of times as great as sucrose. Substituting three chlorine ions for hydroxyl groups on an ordinary sucrose molecule makes Sucralose.