Jmap science
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Oxidizing the methyl groups in caffeine
Could I oxidize the methyl groups of a caffeine to make a organic acid. Caffonic acid I guess.
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Attachment: Caffiene .cml (3kB)
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Thread Moved
24-10-2013 at 16:42 |
Nicodem
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Formal oxidation of any of those methyl groups would give a carbamic acid or an N-cabamoylcarbamic acid. These cannot exist as such, because they
decarboxylate immediately. So, such an oxidation would give theophylline, theobromine, paraxanthine, then the three N-methylxanthines, or ultimately
xanthine itself by complete demethylation.
The oxidative demethylation of caffeine occurs in vivo from the cytochrome P450 oxidase. However, it does not necessarily take the complete oxidation
to a COOH group to cleave the methyl groups.
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Jmap science
Yet another ID of SimpleChemist-238
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I was going to use KmnO4 and caffeine, what would that yield?
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Nicodem
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Probably a mixture of several compounds, depending on the conditions and stoichiometry. The imidazole ring can be oxidized and/or ring opening can
occur. I already posted references for preparative synthesis of caffeine oxidation products (with HCl/H2O2 or HNO3)
in another thread. I suggest you to start by reading those articles. You can additionally check the literature for oxidations with KMnO4.
…there is a human touch of the cultist “believer” in every theorist that he must struggle against as being
unworthy of the scientist. Some of the greatest men of science have publicly repudiated a theory which earlier they hotly defended. In this lies their
scientific temper, not in the scientific defense of the theory. - Weston La Barre (Ghost Dance, 1972)
Read the The ScienceMadness Guidelines!
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