Synthesis of Dulcin

For my final project the first compound I synthesized was Dulcin. Dulcin is an artificial sweetening agent that is 200 times as sweet as sucrose. It is also, the second synthetic sweeter that was discovered. The first synthetic sweetener, saccharin, was discovered five years prior to Dulcin. The discovery of Dulcin occurred in 1883. Approximately seven years after it’s discovery, J.D. Reidel, of Berlin, was able to synthesis Dulcin at a reasonable cost. Once it became possible to synthesis at a reasonable cost, mass production of the sweetener began. Dulcin was favored over its competitor, Saccharin, because it did not possess a bitter aftertaste. For a very brief period of time Dulcin was marketed in the United States as a sucrose substitute. However, in 1954, commercial use was discontinued after the artificial sweetener was found to be toxic.

Artificial sweetening agents play an extremely important role in society. They are important medically as food additives for diabetics, because they must limit their sugar intake. Another example of their importance can be seen through the food industry because of the national concern with diet and weight control. Unfortunately, there is evidence that artificial sweeteners can have undesirable effects. Dulcin, for example, is a very sweet substance which prolonged use can lead to toxic effects resulting from its conversion to para-aminophenol in the body. Para-aminophenol can induce chromosomal aberrations in human lymphocytes (DNA cleavage). Several indications have also been made that saccharin is a mild carcinogen. It was only recently that a new, apparently safe, artificial sweetener NutraSweet has appeared.

One of the major problems chemists face while developing new sweetening agents is that there is no apparent relationship between structure and activity. Some of the strongest sweeteners have structures bearing no relationship to sugars. Another problem faced by chemists is that even a minor change to the