Saccharin (Sweet, sweet amination)

Saccharin, like so many sweeteners, was discovered by accident. From the Wikipedia article:

Saccharin's sweetness was accidentally discovered by Ira Remsen, a professor at Johns Hopkins University, and Constantin Fahlberg, a research fellow working in Remsen's lab. In 1879, while working with coal tar derivatives (toluene), Remsen discovered saccharin's sweetness at dinner after not thoroughly washing his hands, as did Fahlberg during lunch. Remsen and Fahlberg jointly published their discovery in 1880 (Fahlberg, C.; Remsen, I. Ãber die Oxydation des Orthotoluolsulfamids. Chem. Ber. 1879, 12, 469-473). However, in 1884, Fahlberg went on to patent and mass-produce saccharin without ever mentioning Remsen. Fahlberg grew wealthy, while Remsen merely grew irate. On the matter, Remsen commented, "Fahlberg is a scoundrel. It nauseates me to hear my name mentioned in the same breath with him".

There isn't much to say about saccharin as a sweetener that you don't know. It's unpopular these days, and was nearly banned in the States repeatedly. It still finds its way into the pink sweetener packets, some gums, and some drinks (not many - for the most part, people use Sucralose, aspartame, and Ace-K these days.

i-6c0346064c298f03b37c76ee2e66a094-saccharin.gif

Interestingly, saccharin sometimes finds its way into chemical synthesis. A reaction known as the Gabriel synthesis uses potassium pthalimide, which is pretty similar stuff:

i-5e91eaf8c20720f66cb3597badf0da34-phthalimide.gif

Turns out you can do a Gabriel synthesis with saccharin!

Tags

More like this

By Myra L. Karstadt, Ph.D   Did you enjoy your acesulfame today?  How much did you eat?  Do you know whether acesulfame is safe to eat?  Those are not trick questions.  Acesulfame is currently one of the best-selling artificial sweeteners in America, but itâs likely that very few people even…
Whenever I mention artificial sweeteners, it seems to rouse a fight about what's safe, what's not, saccharin this, Stevia that. Around the time saccharin was discovered, another sweetener came on the market: dulcin. I'm not sure how dangerous it is relative to saccharin - it was banned due to…
Clifford S. Mintz Ph.D., author of Bio Job Blog, writes about a study suggesting that artificial sweeteners may cause people to gain rather than lose weight. Like Cliff, I had heard reports of this but never paid much attention. Although the study was published several months ago, I recently…
It's been recognized for a few years that drinking diet sodas can actually cause weight gain, since the phony sweetness of artificial sweeteners disrupts the "predictive relationship" between a sweet taste and caloric satisfaction. In other words, people drink a diet Coke when they are craving a…

Sodium saccharine arrives as the dihydrate. If you wish to do a Gabriel synthesis you must dry it at 110 C and powder the resulting soft brittle cake. Even done in the hood under stringent containment procedures you will be tasting saccharine - and the folks on either side of you probably will also. 300-500 times as sweet as sucrose.

So what's up with aspartame and all those other 'fake sugars' these days? Like many people, I grew up amidst confident, though never quite backed-up, assertions that artificial sweeteners "gave cancer to lab rats."

What's the thinking about their safety, these days?

The aspartame claims are bogus, probably half the meat and veggies you consume have a DF sequence somewhere in there. Of course the methanol is a concern but you're also making formaldehyde every second in your body by deacetylating proteins as a normal course of biology.

Sucralose is probably okay, since it basically passes through your body (just like how you'd think that benzoic acid is horrible, but you pee it straight out). I wonder if urine tastes sweet after sucralose consumption.

Are you Katie Sharpe of H-B Woodlawn origin?
I find it funny that the health/eco conscious crowd uses Stevia, which is the most specious of all of the sweeteners, if you ask me.