I recently came across some creatine powder ~99%. I was thinking about what I could do with this and was interested in trying to figure out the
conditions needed to decarboxalate it.
I know the classical conditions for decarboxylation include a high boiling point solvent, a ketone (cyclohexone or acetone) as well as in some cases
copper salts to catalyze the reaction.
1) I am unsure if the dimethyl guanidine left would remain or would degrade under these conditions.
I have found very little information about conditions needed to hydrolyze creatine (to form acetic acid , MeOH, and guanidine.)
2)Would strong acidic conditions (acid hydrolysis) decompose the guanidine?
Just looking for something fun to use this stuff for, since I am not really interested in eating it. Any suggestions are welcome.
Thanks
EndoNicodem - 27-12-2006 at 12:18
Quote:
Originally posted by Endo
I know the classical conditions for decarboxylation include a high boiling point solvent, a ketone (cyclohexone or acetone) as well as in some cases
copper salts to catalyze the reaction.
Creatine obviously can not be decarboxylated by the use of ketone as catalyst since this requires an alpha -NH2 group (or utmost an -NHR) in order to
form the imine/enamine intermediate. Perhaps it decarboxylates by pyrolysis of its hydrochloride or under other such conditions, but I have not
checked the literature (do that yourself if you can).
Quote:
I have found very little information about conditions needed to hydrolyze creatine (to form acetic acid , MeOH, and guanidine.)
Hydrolyze which bond? There is nothing to hydrolyze in creatine. Utmost one could hydrolyze the guanidine part to 2 equivalents of ammonia, CO2 and
N-methylglycine, but I have no idea of how harsh the required conditions would have to be.Endo - 27-12-2006 at 15:11
Nicodem,
Thanks for the quick reply.
I have looked at the old ochem notebook and I now see that I had picked up a misunderstanding of how decarboxylation occurs.
Without a NH2 or a diketone in the alpha position the carboxolic acid is not going anywhere.
After doing some searching I found this link that indicates hydrolysis to urea and n-methyl glycene.
In any case it indicates to me that the contrary to my expectations the guanidine section is indeed the only portion that can easily be broken down.
On a side note N-methyl glycene has been studied in combination with some drugs to help with schizophrenia. Since this doesn't intrest me, I will
look into using it is a starting block for some other experments.
