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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: soccerfreak13 on May 16, 2005, 05:45:35 PM

Title: glucosamine
Post by: soccerfreak13 on May 16, 2005, 05:45:35 PM
I have a few questions about glucosamine. I know that glucosamine is an amino sugar that are bodies make for our cartilage. It's also used as a "starting" material for tendons and cartilage. Many people who have arthritis use creams and pills containg glucosamine to ease or eliminate the pain, but what if I were to conduct an experiment  to extract glucosamine from a pain relieving cream product such as JointFlex to see how much glucosamine it contained, how would I conduct the experiment. In otherwords, how would I separate the glucosamine from the other ingredients? How would I measure the amount? And what materials would I use in the experiment?

Thank You.
Title: Re:glucosamine
Post by: Froggirl on May 16, 2005, 08:04:08 PM
Well basically you are looking at methods to separate out mixtures.
Most common method for doing this is by using some form of column chromatography.

Since glucosamine has an amino group (see below) you could probably get away with ion exchange chromatography.
This is where the column you introduce the sample onto has charged acid groups that can "grab" onto the basic molecules of glucosamine and hang on to them, letting everything else keep going. Then you just elute the column with a basic solution you make it "let go" of the glucosamine and collect it at the bottom. Then you could evaporate off the water and be left with glucosamine.

So yeah all you would need is a column, some "dowex 50 (H+)" ion exchange resin and various acidic/basic solutions.

Only problem with this method is that it goes on the theory that there is nothing else with basic groups in the mixture.
Title: Re:glucosamine
Post by: soccerfreak13 on May 17, 2005, 11:34:42 AM
What do you mean by "So yeah all you would need is a column, some "dowex 50 (H+)" ion exchange resin and various acidic/basic solutions."

Title: Re:glucosamine
Post by: Mitch on May 17, 2005, 12:52:11 PM
You just need an extraction method and a GC-MS should do what your looking for.
Title: Re:glucosamine
Post by: soccerfreak13 on May 17, 2005, 03:20:45 PM
FROGGIRL: "Then you just elute the column with a basic solution you make it "let go" of the glucosamine and collect it at the bottom."
 

What basic/acid solutions would you recommend?

Also is glucosamine organic?
Title: Re:glucosamine
Post by: soccerfreak13 on May 17, 2005, 07:20:59 PM
I don't understand something. If I'm to use a GC-MS wouldn't it have to be a gas because what im trying to extract glucosamine from is a cream, not a gas.
Title: Re:glucosamine
Post by: Froggirl on May 17, 2005, 11:23:27 PM
GC-MS is just a way of checking that what you've actually got is glucosamine. You could also use something like an NMR etc. Something that will give you structural/molecular weight etc data that you can use to validate your compound.

I would use solutions of ~1M NaOH and HCl solutions for the extraction process.

And yes, tehcnically glucosamine is organic.

Dowex 50 is just a sort of resin that you can pack a column with. You can buy it from places like sigma-aldrich.
Title: Re:glucosamine
Post by: Mitch on May 17, 2005, 11:33:59 PM
NMR will not allow him to quanitate his sample, which is what he asked.
Title: Re:glucosamine
Post by: janne18 on May 18, 2005, 12:22:08 PM
I'm not an expert in analytic chemisty, but I think using a LC-MS is a better choice than GC-MS. With a LC-MS you have a liquid and that's better with a matrix like cream.
Title: Re:glucosamine
Post by: soccerfreak13 on May 18, 2005, 05:02:20 PM
What's the difference between the LC-MS AND THE GC-MS?
Which would better to use to extract the glucosamine from a cream?
Title: Re:glucosamine
Post by: soccerfreak13 on May 18, 2005, 06:43:01 PM
ok, so let me get this straight. If I was using a GC-MS or a LC-MS, what would I? What are the steps that I would do in order to find out how to extract the glucosamine?
Title: Re:glucosamine
Post by: soccerfreak13 on May 18, 2005, 06:58:28 PM
how is glucosamine made? because if are bodies produce it, then how are people who make glucosamine pills able to get glucosamine into the pills?
Title: Re:glucosamine
Post by: Froggirl on May 18, 2005, 08:04:12 PM
Well I was basing it on the weight of fraction to get an estimation of moles of glucosamine and NMR as a method of checking purity of sample/structure identification

But yes if GC-MS is available its an easy way of quatifying the amount  :)
Title: Re:glucosamine
Post by: Froggirl on May 18, 2005, 08:17:19 PM
They typically extract glucosamine from sellfish I think but there are some companies (eg cargill pharmaceuticals) that have worked out ways for a strain of bacteria to ferment it from corn.

Oral glucosamine is a dietary supplement remember - ie supplementing our natural levels of the substance but there is very little evidence to say the creams work because glucosamine isn't readily absorbed through the skin.

There are tons of references for this sort of stuff on the net.
Title: Re:glucosamine
Post by: soccerfreak13 on May 19, 2005, 05:34:15 PM
okay, how am I supposed to know how much acid/base solutions i'm supposed to add when doing the method, GC-MS? Step-by-step. Won't the other ingredients in the cream interfere with the glucosamine when the GC-MS is trying to calculate the amount of glucosamine the cream has?
Title: Re:glucosamine
Post by: soccerfreak13 on May 21, 2005, 06:21:49 PM
what procedures would I follow in order to extract the glucosamine from a cream? And how would I analyze the data on the amount ogf glucosamine?