Hi guys. I have a mixture of isoflavinoids including the usual isoflavone suspects (daidzein, genistein) plus an isoflavane: equol.
Now, equol doesn't have the ketone group that the other two have. Could this be a basis for separating it from the others?
It looks like it would work, but are there problems regarding steric hinderance? If an adduct can be formed, what's the best thing to do it?
[Edited on 15-12-2010 by Baphomet]scientician - 15-12-2010 at 02:03
I'm assuming simple paper chromatography just wont do?
I sneaked a peek at equol, as well as the other two. Judging by the number of alcohols, I'd have to guess that the two molecules you want to separate
out would exhibit higher solubility in water. Paper chromatography with water could separate the equol out fairly easily. Baphomet - 15-12-2010 at 02:12
Thanks for the idea! However equol has two hydroxyls as well. Just guesstimating but I thought that their solubilities would be so close as to make
chromatography a pain in the ass. Might be wrong though.. Baphomet - 15-12-2010 at 03:07
Thanks for the idea! However equol has two hydroxyls as well. Just guesstimating but I thought that their solubilities would be so close as to make
chromatography a pain in the ass. Might be wrong though.
You can test feasibility with paper cut from coffee
filters
and do multiple runs with differing mixes of ROH:H<sub>2</sub>O.
Cheep is gud.matei - 15-12-2010 at 10:24
Compunds containing carbonyl groups are easily separated using Girard's reagents. You can read more on that in Vogel's Textbook of Organic Chemistry
(5th Ed.) on page 434. Girard's reagent P is more useful than T because it is water soluble and also its carbonyl derivatives are water soluble. A
simple method of separating your mixture will be to dissolve it in an organic solvent (like DCM, ether or whatever) and wash it with a solution of
Girard's regent P in water, so you'll get rid of the carbonyl-containing flavonoids.
However the reagent itself is synthesized starting from ethyl chloroacetate, pyridine and hydrazine hydrate, so it may not be so feasible to make it
after all...
