Author Topic: 3-methylindole from egg white  (Read 953 times)

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Lestat

  • Guest
3-methylindole from egg white
« on: June 22, 2004, 11:24:00 AM »
Ive just read, 3-methylindole (skatole) can be made from egg white by alkali hydrolysis using KOH or NaOH, on mixing brown flakes of 3-methylindole seperate out. I suggest then recrystallisation from a simple water extraction. I am just going to try this out as I type this and will post my results shortly  :)


Lestat

  • Guest
Success I think
« Reply #1 on: June 22, 2004, 02:24:00 PM »
I filtered about a half test tube of the solution, and tried HCl gassing, I ran out of gas in my torch that I was using to boil some HCl and it wouldnt boil, so i just put an equal volume of boiling muriatic acid into the egg solution.

Within a few minutes it had seperated into three layers, with a precipitate of brown flakes in the top layer which I think should be the 3-methylindole  :)


GC_MS

  • Guest
tadaaaa
« Reply #2 on: June 22, 2004, 11:47:00 PM »
Any idea how many and what type of compounds there might be in egg white that can crystallize if you gas it with HCl?


Lestat

  • Guest
I had read on a website on unusual molecules...
« Reply #3 on: June 22, 2004, 11:58:00 PM »
I had read on a website on unusual molecules about 3-methylindole, and the site said that the common synth was KOH/NaOH and the egg white, I had done that but failed to obtain any precipitate, so I just decided to try gassing/HCl in the hope that i would work, I have little experience in organic chem at the moment, but I am learning. I don't see why it cannot work though.


GC_MS

  • Guest
eggs
« Reply #4 on: June 23, 2004, 12:17:00 AM »
A good conversation partner for you would be halfapint (may God have blessed him with a 1000 sex-and-drug-crazed virgins), the OTC precursor searcher par excellence. He found something about extracting indole from cow shit I think.

But to remain in reality (unless you are extremely hopeless), you should take into consideration that an egg is a complex matrix of 100s of different substances, ranging from sugars to nucleosides. If you gas it with HCl, you will precipitate everything that forms solid HCl salts.


Lestat

  • Guest
Indole from COW SHIT!!!!!
« Reply #5 on: June 23, 2004, 12:22:00 AM »
Indole from COW SHIT!!!!! lol may be nasty but at least it's not gonna be controlled any time soon  ;D

I suppose that there is some possibility of 3-methylindole from egg white after alkali hydrolysis though? From what I read, it's supposed to be a brown precipitate that smells like shite, and that seems to be what I have as far as I can tell, unfortunately I am going to have to get somebody else to do the sniff test properly, as I have almost no sense of smell  :(


Lestat

  • Guest
How do I upload a picture, I have just taken a
« Reply #6 on: June 23, 2004, 01:12:00 AM »
How do I upload a picture, I have just taken a picture of my hopeful acid/base  :)


Nicodem

  • Guest
Rather eat those eggs
« Reply #7 on: June 23, 2004, 01:28:00 AM »
Lestat, from which dimension you came from? You mention at least in three posts that you read this somewhere and yet I see no ref or link anywhere. 3-methylindole from eggs! Have you any idea how your experimantation makes me laugh? Have you any idea how bad this compound smell? You would have already know if you would have made it. You think it's gonna pop out of the egg just like that, from thousands of other compounds. Besides don't waste your time with HCl. 3-Me-indole is not basic enough to form salts with HCl.


Lestat

  • Guest
Here is the link, sorry I neglected to post...
« Reply #8 on: June 23, 2004, 01:34:00 AM »
Here is the link, sorry I neglected to post this, I have been rather erm...strung out all night.

http://www.bris.ac.uk/Depts/Chemistry/MOTM/silly/sillymols.htm




Nicodem

  • Guest
A critique of the unscientific approach
« Reply #9 on: June 23, 2004, 08:29:00 AM »
You can’t just take an unscientific sentence from a homepage and deduce a whole synthetic procedure out of it, without knowing anything that goes on in the reaction/extraction or at least about the properties of the compounds involved. Details are very important!

Instead of playing with your eggs you might do a literature search and present what you found at The Hive to start a discussion and a possible alternative use or approach. For example, it might turn out that you need half a kilo of egg albumin or ten dozens of eggs for 100mg of 3-methyl-indole! Maybe even wasting 2L of an expensive solvent and performing a chromatographic column!

And yet, if discussing about the reaction, we might find out that what goes on in the reaction mechanism is actually a simple pyrolysis of the tryptophan from the eggs’ albumin. This might led somebee to the idea of using pure tryptophane and pyrolyse it in the presence of KOH to get some smelly 3-methyl-indole. And maybe some other bee would then realize that that methyl group is actually slightly acidic and could bee made nucleophylic with a proper base. Then some other bee would find a way on how to use this property for some new route to a useful tryptamine. You see, it’s all about doing things with care and the imagination under control.


Lestat

  • Guest
I agree totally.
« Reply #10 on: June 23, 2004, 11:25:00 AM »
Yes, I agree with you 100%, unfortunately I am neither well off or well equipped, and have to improvise ghetto style gear, and the other problem here lies in my lack of experience, I have very little experience as a bee, I could probably manage a birch reduction, an E/I/RP or maybe even a P2P synth, but not much more unfortunately yet.  :(


xxxxx

  • Guest
try to get the tryptophan
« Reply #11 on: June 23, 2004, 01:19:00 PM »
there was a time when i thought i might take the tryptophan from foods which have a high content of this amino acid, such as turkey. even turkey has only about 2% dry weight of this comparativly scarce amino acid, however. anyway my plan was to hydrolyse the protiens to the amino acids with hcl, as in the stomach, and then precipitate the tryptophan by slowly increasing/decreasing the ph to take advantage of the different soluabilities of amino acids at their different isoelectronic points. even so the precipitated tryptophan would be mixed with at least one other amino acid, but could be separated from these by some other method. of course i planned to collect the tyrosine too.

Lestat

  • Guest
How did your little turkey extracting session...
« Reply #12 on: June 23, 2004, 01:53:00 PM »
How did your little turkey extracting session go?
I think there's a nice looking tryptamine synth from milk caseine on rhodiums site, im looking now. ;D


xxxxx

  • Guest
never actually did it
« Reply #13 on: June 23, 2004, 02:09:00 PM »
i never actually did this, but i really did have the research all done, including the isoelectronic figures for all the amino acids and solvents to separate the tryptophan from the other amino acids. then i found a place that sold four ounces of 99% tryptophan for us $15.

lugh

  • Guest
Literature Search Results
« Reply #14 on: June 23, 2004, 07:03:00 PM »
A couple of relevant papers from a short literature search on the subject of skatole:

Herter and Foster, J Biol Chem 2 267-70 (1906)



and

Redgrove, The Perfumery and Essential Oil Record pp 193-5 June (1929)



As far as caustic fusion of proteins to get indoles, Polythene_Sam is one of the bees that has posted some useful information;



;)


wad

  • Guest
Proteins can be hydrolysed by fermentation...
« Reply #15 on: June 24, 2004, 03:56:00 AM »
Proteins can be hydrolysed by fermentation pills for stomach.

Lestat

  • Guest
Lugh, how do I open those links that you so...
« Reply #16 on: June 24, 2004, 11:34:00 AM »
Lugh, how do I open those links that you so kindly posted, it just says opening xxx...cannot find server.  :(


lugh

  • Guest
Browser Options
« Reply #17 on: June 24, 2004, 12:04:00 PM »
That would depend on your browser, with Internet Explorer you would use right click and select Save Target As; with Netscape and Mozilla, you would right click and select Save Link As  ;)


Lestat

  • Guest
The link must be buggered, it doesn't work.
« Reply #18 on: June 24, 2004, 12:06:00 PM »
The link must be buggered, it doesn't work.


lugh

  • Guest
Browser Problems
« Reply #19 on: June 24, 2004, 12:37:00 PM »
The link works fine, so it must bee your browser that's buggered; unless it's operator error  :P