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Topic: Separating an ester from steroid  (Read 3116 times)

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Offline biohacker2020

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Separating an ester from steroid
« on: October 24, 2017, 11:50:26 AM »
Hey guys, my first time posting here.

Lets say there is a steroid with a propionate ester attached to it dissolved in carrier oil at 100mg/ml and the goal is to separate the ester from the steroid. The steroid has a molar mass of 304.46 g/mol and the weight with the propionic acid ester is 360.538 g/mol.

How would I separate the propionic acid from the steroid base. I was thinking perhaps adding water to the solution and heating it up, since propionic acid is soluble in water and the steroid has minimal solubility in water.

Thanks in advance.

Offline wildfyr

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Re: Separating an ester from steroid
« Reply #1 on: October 24, 2017, 06:14:15 PM »
Seems right to me. Not sure you need heating, more likely just a solid bit of agitation. If that doesn't work, maybe extract it into aqueous sodium bicarbonate aolution, toss out the oil, then add a volatile non water misicble organic like ethyl acetate or chlorform and enough dilute acid to neutralize the bicarbonate. The product should then transfer back into the organic layer, which is easy to evaporate.

Offline Arkcon

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Re: Separating an ester from steroid
« Reply #2 on: October 24, 2017, 08:51:07 PM »
Hey guys, my first time posting here.

Lets say there is a steroid with a propionate ester attached

OK.  I suppose you mean propionate ester of a steroid.  Funny way to put it, but OK.

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to it dissolved in carrier oil at 100mg/ml and the goal is to separate the ester from the steroid. The steroid has a molar mass of 304.46 g/mol and the weight with the propionic acid ester is 360.538 g/mol.

Uhh.  This info really isn't pertinant to the rest of your question.

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How would I separate the propionic acid from the steroid base. I was thinking perhaps adding water to the solution and heating it up,


I don't think that will work.

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since propionic acid is soluble in water and the steroid has minimal solubility in water.

Not really.  Just because the two "parts" have different solubility, doesn't mean the reaction to break them apart will work.  You aren't too far wrong, but only by accident, really.

See here: https://en.wikipedia.org/wiki/Ester#Addition_of_nucleophiles_at_carbonyl

A weak acid or base should split it apart, then you will see the two components partitioning into water or solvent as appropriate.  You may also get side reactions with your "steroid" with no name.

Listen, biohacker2020:, I'd like to welcome you and all the new chemists to the Chemical Forums.  But I'd like to ask you to trouble yourself to read our Forum Rules{click}. You already accepted them when you signed up for our forum, and you have to follow them, whether you agree with them or not, or even if you're unaware of them. 

Our rules specify that we want to see your work, and then, we want to give you hints, so that you learn for yourself.  It doesn't matter if you're a new student, or a dedicated amateur, we need to know what you know, and what you think, so we know what level you're at, so we can give useful hints, so your knowledge can grow.   

Your question is very specific, for someone with no apparent expertise at all, not even knowledge of the terminology.  This isn't a druggie kiddie ohlookitwhaticando forum.  We don't give procedures for self medication, and we don't discuss drugs of abuse of any kind.  I hope, if you want to talk more about this topic, you'll keep the topic -- theoretical.
Hey, I'm not judging.  I just like to shoot straight.  I'm a man of science.

Offline biohacker2020

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Re: Separating an ester from steroid
« Reply #3 on: October 25, 2017, 05:16:40 AM »
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OK.  I suppose you mean propionate ester of a steroid.  Funny way to put it, but OK.

Yes. 2α-methyl-4,5α-dihydrotestosterone. English is not my first language.

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Uhh.  This info really isn't pertinant to the rest of your question.

I wanted to put as much information about the reagent.

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I don't think that will work

I'll add a magnetic stir bar to catalyse the reaction as wildfyr pointed out.


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Not really.  Just because the two "parts" have different solubility, doesn't mean the reaction to break them apart will work.  You aren't too far wrong, but only by accident, really.

See here: https://en.wikipedia.org/wiki/Ester#Addition_of_nucleophiles_at_carbonyl

A weak acid or base should split it apart, then you will see the two components partitioning into water or solvent as appropriate.  You may also get side reactions with your "steroid" with no name.

I have read that addition of water is one way of doing hydrolysis but the slowest, but also with least side reactions. http://www.chemguide.co.uk/organicprops/esters/hydrolysis.html

Thanks, I'll add NaOH but I am thinking that side reactions that might occur might greatly reduce my yield.

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Listen, biohacker2020:, I'd like to welcome you and all the new chemists to the Chemical Forums.  But I'd like to ask you to trouble yourself to read our Forum Rules{click}. You already accepted them when you signed up for our forum, and you have to follow them, whether you agree with them or not, or even if you're unaware of them. 

Our rules specify that we want to see your work, and then, we want to give you hints, so that you learn for yourself.  It doesn't matter if you're a new student, or a dedicated amateur, we need to know what you know, and what you think, so we know what level you're at, so we can give useful hints, so your knowledge can grow.   

Your question is very specific, for someone with no apparent expertise at all, not even knowledge of the terminology.  This isn't a druggie kiddie ohlookitwhaticando forum.  We don't give procedures for self medication, and we don't discuss drugs of abuse of any kind.  I hope, if you want to talk more about this topic, you'll keep the topic -- theoretical.

Thanks.

LOL, I am working on extended essay in Bio and I want to write a paper on how Drostanolone affects 5a Reductase activity in skin cells.

My Chem knowledge is really bad and I can't really do the experiment without it. Esters is something I have been having trouble with understanding so I thought its half term break now, this would be the best place to ask questions about it.

Offline Arkcon

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Re: Separating an ester from steroid
« Reply #4 on: October 25, 2017, 07:05:21 AM »
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I'll add a magnetic stir bar to catalyse the reaction as wildfyr pointed out.

Con you use your best chemist knowledge to substantiate that point of view?
Hey, I'm not judging.  I just like to shoot straight.  I'm a man of science.

Offline biohacker2020

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Re: Separating an ester from steroid
« Reply #5 on: October 25, 2017, 12:58:35 PM »
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Con you use your best chemist knowledge to substantiate that point of view?

I don't get what are you trying to do asking me this?

Before reading the rest of your reply I thought that perhaps reaction time would be too slow without stirring and you meant that it won't work because of that, since according to Collision theory the more you stir it the more the molecules will collide and thus faster the reaction rate.

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