Saccharine

Formula name - C7H5NO3S

History - Saccharin's sweetness was accidentally discovered in 1879 by Ira Remsen, a professor at Johns Hopkins University, and Constantin Fahlberg, a research fellow working in Remsen's lab while working with coal tar derivatives (toluene). In 1901- John F. Queeny founds the original Monsanto, his wife was Olga Monsanto Queeny, and the first product of that company was saccharine (from Monsantos Company History found at http://www.monsanto.com/monsanto/layout/about_us/timeline/default.asp)!

Saccharin is valued because it is not metabolized by the human body and therefore does not contribute to daily calorie in-take. It does not affect blood insulin levels, and has effectively no food energy. Saccharin can be produced in various ways. Remsen & Fahlberg's original route starts with toluene, but yields from this starting point are small. In 1950, an improved synthesis was developed at the Maumee Chemical Company of Toledo, Ohio. In this synthesis, anthranilic acid successively reacts with nitrous acid, sulfur dioxide and chlorine, and then ammonia to yield saccharin. Another route begins with o-chlorotoluene. (Bungard, 1967)

Production Abstract - Anodic oxidation of o-toluenesulphonamide to saccharine on a NiO(OH)-coated nickel anode

• by Jaromír Hlavatý, Viktor Bakos and Jií Volke
• from the Journal of Applied Electrochemistry published by Springer Netherlands
• ISSN 0021-891X (Print) 1572-8838 (Online) on the subject of Chemistry and Materials Science.
• DOI - 10.1007/BF01023607, pages 1228-1233, J.
• Heyrovský Institute of Physical Chemistry and Electrochemistry, Czechoslovak Academy of Sciences, Vlaská 9, 118 40 Prague 1, Czechoslovaki
• Received: 23 January 1987  Revised: 16 May 1987  

o-Toluenesulphonamide has been electrolytically oxidized at low current density to saccharine in aqueous solutions of alkali carbonates on anodes coated with NiO(OH). This electrolytic oxidation led to a 40% yield of saccharine. The application of carbon and glassy-carbon counter electrodes or of various supports for the working electrodes did not result in improved saccharine yield. Moreover, the choice of a different potential and a different current density or the use of organic co-solvents did not substantially affect the course of the electrolytic oxidation. In the electrolytic oxidation ofo-toluenesulphonamide a parasitic evolution of oxygen occurred which caused a partial degradation of the starting material. In strongly alkaline media, i.e. in aqueous solutions of alkali hydroxides, a fission of the NH₂ group with formation ofo-toluenesulphonate occurred during the electrolysis.

Chemical composition - The chemical formula for saccharin is C₇H₅NO₃S. The molar mass for saccharin is 183.19 grams per mole. Saccharin consists mostly of carbon; carbon makes up 45.89% of the composition of saccharin by mass. The mass of saccharin is also 2.75% hydrogen, 7.65% nitrogen, 26.20% oxygen, and 17.50% sulfur. By number saccharin is 41% carbon, 29% hydrogen, 6% nitrogen, 18% oxygen, and 6% sulfur. Saccharin melts at 228.8° to 229.7° C. Structurally, saccharin is made up of two connected rings; the first ring is a phenyl ring and the second is a 5 membered ring with a nitrogen, a carboxyl group, and a sulfone group beside the nitrogen. Due to the presence of a nitrogen, the molecule is heterocyclic.

Chemical Sampling by OSHA

Potential symptoms: Irritation of skin; at very high levels: loss of appetite, nausea, vomiting, diarrhea; in male rats: bladder cancer.

Affected organ: Skin

Notes:

1. Reclassification of saccharin by the IARC from Group 2B (possibly carcinogenic to humans) to Group 3 has remained controversial.
2. Saccharin is permitted by the FDA for use as a sweetener in amounts up to 12 milligrams per fluid ounce or up to 30 milligrams per designated serving size in processed foods (21 CFR 180.37)
3. The measurement of saccharin in urine has been proposed as a biomarker of dietary exposure

Although saccharin was commercialized not long after its discovery, it was not until sugar rationing during World War I that its use became widespread. Its popularity further increased during the 1960s and 1970s among dieters, since saccharin is a calorie-free sweetener. In the United States saccharin is often found in restaurants in pink packets; the most popular brand is "Sweet'N Low". A small number of soft drinks are sweetened with saccharin, the most popular being the Coca-Cola Company's cola drink Tab, introduced in 1963 as a diet soft drink.