Is this molecular combination even possible? Can you add a citrate group to any flavanoid for that matter?
Any Biochemist?
Started by
Ironman
, May 16 2008 01:42 AM
2 replies to this topic
#1
Posted 16 May 2008 - 01:42 AM
Is this molecular combination even possible? Can you add a citrate group to any flavanoid for that matter?
#2
Posted 16 May 2008 - 02:15 AM
Resveratrol is not technically a flavonoid, but for purposes of this discussion that's not important. The only functional groups on resveratrol are hydroxyls, and they are not very reactive. It's possible to create a citrate ester of resveratrol, where the carboxyl carbon of the citrate (or any organic acid) is covalently bound to the oxygen atom of one of the hydroxyls. It would be kind of hard to do this to a specific hydroxyl, although you could do it to all of them without a huge amount of trouble. I'm not sure why you'd want to, though. People have made resveratrol esters of acetic acid, using the 4' hydroxyl. This creates a compound that is more active in vivo than plain resveratrol. Because it is fairly polar, I'm not sure that citric acid would work in the same way though. In order to create a citrate salt, you'd need to combine citric acid with a base, like an amine. Resveratrol is a very weak acid, so if it did form a salt, it would be negatively charged (this would require a pH above 10 or so, very alkaline) so the counterion would need to be positively charged, like sodium.Is this molecular combination even possible? Can you add a citrate group to any flavanoid for that matter?
So... true resveratrol citrate is possible to make, but I'm not exactly sure why anyone would want to.
#3
Posted 16 May 2008 - 02:56 AM
OK. Need to digest all that. I've seen some compounds with citrate attached that had better pharmacokinetics and just hadn't seen a citrate version of resveratrol talked about. Thanks.
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