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Topic: acid hydrolysis of glycoside  (Read 4259 times)

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Offline StevenC

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acid hydrolysis of glycoside
« on: August 03, 2016, 12:14:18 PM »
Since I cannot use strong acids to hydrolyze a glycoside (molecule with a glucose molecule), I am using a weak acid (such as ascorbic acid, which I can get without ordering at a chemistry store).

Is this possible? Will the reaction take a long time? Will the acid eventually grow weaker or does it stay just as acid as it only catalyses the reaction (and not reacts with anything so the acid stays the same, just as acid as in the start)?

How can I speed up the reaction? Can I do that with shaking the solution?

After a long period (like one year) passes, does all the diosmin (glycoside) convert into diosmetin (aglycone)?

Offline orthoformate

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Re: acid hydrolysis of glycoside
« Reply #1 on: August 03, 2016, 11:36:05 PM »
Can you draw the hydrolysis mechanism? This will show you whether or not the acid will be consumed, or if it will just act as a catalyst.

you can purchase Muriatic acid (HCl in H2O) at your local hardware store.

Offline StevenC

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Re: acid hydrolysis of glycoside
« Reply #2 on: August 04, 2016, 03:10:31 AM »
I don't know the hydrolysis mechanism.

But I have an idea, I am going to use a pH strip to see if acidity decreased or not.

Offline kriggy

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Re: acid hydrolysis of glycoside
« Reply #3 on: August 04, 2016, 05:42:04 AM »
THat might work but pH strips are not realy precise for that kind of measurment. I suppose you google ester or ether hydrolysis mechanism and you can figure out if the acid is consumed or not


Offline StevenC

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Re: acid hydrolysis of glycoside
« Reply #5 on: August 05, 2016, 12:27:25 PM »
This article:

http://www.academicjournals.org/article/article1380788329_Wang%20et%20al%201.pdf

Is talking about the hydrolyzing acids as catalysts. Does that mean that ascorbic acid is acting as a catalyst?

Offline orgopete

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Re: acid hydrolysis of glycoside
« Reply #6 on: August 07, 2016, 11:40:43 AM »
Since I cannot use strong acids to hydrolyze a glycoside (molecule with a glucose molecule), I am using a weak acid (such as ascorbic acid, which I can get without ordering at a chemistry store).

Is this possible? Will the reaction take a long time? Will the acid eventually grow weaker or does it stay just as acid as it only catalyses the reaction (and not reacts with anything so the acid stays the same, just as acid as in the start)?

How can I speed up the reaction? Can I do that with shaking the solution?

After a long period (like one year) passes, does all the diosmin (glycoside) convert into diosmetin (aglycone)?

This question borders on drugs, but in this case not banned ones. Is the poster asking about modifying a drug for self treatment? Should we help? The chemistry is simple enough so if he or she can get diosmin, then why isn't the aglycone also available? I might think there are other analogs of diosmetin that should have similar biological activity. Perhaps the poster could assure us we are not participating and a phase X drug trial.
Author of a multi-tiered example based workbook for learning organic chemistry mechanisms.

Offline StevenC

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Re: acid hydrolysis of glycoside
« Reply #7 on: August 08, 2016, 12:42:19 AM »
I found out that they sell diosmetin (the aglycone) from China. Is it a good idea to order from them or should I hydrolyze diosmin myself to get diosmetin?

By the way, I use very small dosages (50 mg) of diosmetin for medical reasons.
« Last Edit: August 08, 2016, 03:56:37 AM by StevenC »

Offline Arkcon

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Re: acid hydrolysis of glycoside
« Reply #8 on: August 08, 2016, 05:33:40 AM »
StevenC: kindly trouble yourself to re-read the Forum Rules{click} You agreed to the rules when you signed up for this board, and we expect you to follow them.  We don't give help on self-medication.  This was a fine enough thread, although a little circular, as we defined andre-defined a process, but its done now.

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Hey, I'm not judging.  I just like to shoot straight.  I'm a man of science.

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