Skatole?

I read that skatole could be made by reacting KOH and egg whites, probably from the tryptophan in the egg. Obviously it wouldn't be a good method for producing large amounts of it but I thought it would be interesting.
The KOH pellets were added to a film canister and egg white poured onto them, no reaction occured immediately so I capped and shook it and then left it to settle to the bottom. It formed a gelatinous lump at the bottom and warmed slightly (chemical omelet ) but had no poo smell, just the slight eggish scent and KOH fumes.
I then heated it in boiling water and stirred the lump, forming a yellow foamy liquid but still no smell.
What's the story? Was that just a bad source of info or is there something wrong with how I did it?

I don't have any easy way of getting propanal I could maybe find some propylene glycol and make it from that though, MEK could be substituted for 2,3 dimethylindole which would probably smell similar... I think I would be banned from chemistry if I were to make a reasonable amount though

Quote: Originally posted by hissingnoise

You do know that in trace amounts skatole smells sweet - but large quantities have a terrible spong. . .

Hehehehe
I've got some indole-3-butyric acid for my garden but it's a very dilute and expensive, plus that would give ethyl indole anyway. I would only be making a tiny amount, then the whole mix would probably be flushed down the toilet, where skatole belongs

Occurred to me last night: if indole is readily available for you, I'm pretty sure you could add a methyl to the 3-position (namely, create skatole) by refluxing with methanol and a bit of sulfuric acid.

It works on toluene - a long time ago I created 1,3,5-trimethylbenzene, a red oil, by doing so.

You could perform the Fischer indole synthesis with acetaldehyde/phenylhydrazine to get indole if you can't find it for whatever reason. Both are easily within reach.

Granted it wouldn't be the cleanest reaction, but I'm guessing a little bit of skatole goes a long way. Worth looking into I think - if I find any references that offer credence to this theory I'll post them.

Quote: Originally posted by zed

What component, of the odor of feces, is actually supplied by Skatole? Gases, certain amines, and free fatty acids, all pack a pungent punch of their own.

I intend to find this out

Quote: Originally posted by madscientist

Occurred to me last night: if indole is readily available for you, I'm pretty sure you could add a methyl to the 3-position (namely, create skatole) by refluxing with methanol and a bit of sulfuric acid. It works on toluene - a long time ago I created 1,3,5-trimethylbenzene, a red oil, by doing so.

Spong,

We all know you got that reference from Merck Index. When they are speaking of albumin, they are not talking of egg whites. Rather, it is usually the freeze dried or carefully dessicated (so as not to denature the protein). As you know, some proteins can tie up a LOT of H2O in their matrices. Also, you should know albumin could refer to plasma protein in a number of living things. Here they probably are talking about the powdered, finely milled, dessicated egg white powder. Your best bet is to go to some of the steroid brain places. They sell pure whey, pure albumin, and other top of the foodchain types of protein. My suggestion: have dedicated disposable heating retort (like iron pipe with one cap on bottom) to perform such reactions. They could really mess up any remaining glassware you may have. Hope the info helped! Now, there is one other route, but it ain't pretty: ever heard of the Atkins Diet or South Beach diet - basically high protein low carb diets. You can easily detect skatol in your regular skat, but you will greatly increase the yield by digesting more of these high protein foods. Especially milk, egg, etc. The extraction would make a stone man barf, but....there probably are better ways. Hope the insight helped!

It was from the molecules with silly names website Argh albumen and albumin are so similarly spelled.
I read about extracting almumIn from fresh eggs with ammonium sulfate and acetic acid, we have chickens so I've got a lot of eggs to practice on