Acetylsalicylic Acid Solubilty

[Khushi]

I've been doing research on Aspirin(Acetylsalicylic Acid). One thing I need to know is about it's solubility in water. I know that Acetylsalicylic acid isn't very soluble in water. I've tried researching on the net and so far i haven't really got it, but I think i'm onto something. Basically I think that Acetylsalicylic Acid isn't very soluble in water because of it's polarity. Water is a polar molecule, and I think Acetylsalicylic Acid isn't. That's all i got so far...:S...so if anyone could help understand it more like how is Acetylsalicylic Acid a non polar molecule?...please do. I really don't think that two line explanation is worth anything. And what would be a good solvent for Acetylsalicylic Acid...oviously a non polar solvent right?..."like dissolves like"

[RyanJ]

It is soluable in water < 0.1 g/100 mL at 23 Degrees C

 

Source: http://chemfinder.cambridgesoft.com/

 

Cheers,

 

Ryan Jones

[akcapr]

ryan there was no point to that post- he already knew it was slightly soluable . gosh

[Khushi]

*she ...lol

 

i wanted to know how to determine the polarity of Acetylsalicylic Acid

[akcapr]

ya she. but to find polarity you have to draw the molecule and find the shape (molecular geometry), then you compare the elctronegativities. For example, for H2O the shape is... bent planar. so then comapre the elctronegatives and you will see that the Oxygen is more electronegative and is thus more "negative" than the relatively positive Hydrogens. Thus, it is polar. For another compound such as AlH3, the molecule is a trigonal planar.

 

 

Thus, no matter what, it will not be polar because the charge will be distributed in no one direction.

 

For Aspirin it would be more complicated since it has no single shape.

 

 

Also, when aspirin hits acid pH in the stomach it actually can lose a hydrogen which can change the polarity to become more soluable. Since aspirin is polar in some spots, primarily the O bonds, its slightly soluable in water. C-H bonds are only slightly polar.

[Ilja]

Try to solve it in Ethanol (C2H5OH) i think it will work better than if u do it with water.

[RyanJ]

Try to solve it in Ethanol (C2H5OH) i think it will work better than if u do it with water.

 

It should, maybe if people drank a load of ethanol their headaches would do faster after they itook the tablets

 

Cheers,

 

Ryan Jones

[YT2095]

actualy ASA dissolves very well in Ethanol or Methanol, it`s used as a way to remove the pure ASA from the buffer agents in the tablets (often Chalk).

[jdurg]

It should' date=' maybe if people drank a load of ethanol their headaches would do faster after they itook the tablets

 

Cheers,

 

Ryan Jones[/quote']

 

 

Just in case people aren't aware, you should NEVER, EVER drink ethanol while also taking acetylsalicylic acid. The toxic byproducts produced in your liver WILL kill you. Acetaminophen and Acetylsalicylic acid, when processed along with ethanol, produce some of the most potent hepatotoxic compounds you can find. This is why they put those warnings on the bottles saying that if you drink a certain amount of alcohol you shouldn't use this drug.

[RyanJ]

Just in case people aren't aware, you should NEVER, EVER drink ethanol while also taking acetylsalicylic acid. The toxic byproducts produced in your liver WILL kill you. Acetaminophen and Acetylsalicylic acid, when processed along with ethanol, produce some of the most potent hepatotoxic compounds you can find. This is why they put those warnings on the bottles saying that if you drink a certain amount of alcohol you shouldn't use this drug.

 

 

Good point, I should have put "but the headache it will give you would be far more severe".

 

I did not know it could kill you, I did know it would do you a lot of harm though....

 

Cheers,

 

Ryan Jones

[warut]

What are those hepatotoxic compounds?

[RyanJ]

What are those hepatotoxic compounds?

 

Hepatotoxic are chemicals that attack or damage the liver - one of the worst types as it is the liver that filters out all these nasty toxins from the blood in the first place.

 

As for the exact compounds formed in the reaction I cannot help you there sorry

 

Cheers,

 

Ryan Jones

[jdurg]

The main toxic compound resulting from the metabolism of acetaminophen is N-acetyl-benzoquinoneimine (NAPQI). This compound is quite toxic and is produced by the liver whenever acetaminophen is metabolised. Normally, there are plenty of other enzymes and proteins in the liver which can bind to the NAPQI and render it harmless. However, when combined with alcohol or long term alcohol use, the toxic metabolite is unable to be bound to these specific enzymes/proteins and instead bind to the liver itself. Glutathione is the main compound which can bind NAPQI and render it harmless. Excessive alcohol consumption can basically deactivate the Glutathione and allow the NAPQI to simply destroy your liver.

[warut]

Thanks! I've known for a long time that acetaminophen (i.e. paracetamol in some other countries) is hepatotoxic but never knew exactly why. So those hepatitis B or C carriers should try to avoid using this drug.

[Khushi]

thanks....this is all really helping:)

[Jule Bale]

actualy ASA dissolves very well in Ethanol or Methanol, it`s used as a way to remove the pure ASA from the buffer agents in the tablets (often Chalk).

 

Why? I'm just curious

[mississippichem]

Why? I'm just curious

 

The carboxylic acid functionality can receive hydrogen bonds from -OH groups of alcohols.

[John Cuthber]

Just in case people aren't aware, you should NEVER, EVER drink ethanol while also taking acetylsalicylic acid. The toxic byproducts produced in your liver WILL kill you. Acetaminophen and Acetylsalicylic acid, when processed along with ethanol, produce some of the most potent hepatotoxic compounds you can find. This is why they put those warnings on the bottles saying that if you drink a certain amount of alcohol you shouldn't use this drug.

 

That's interesting.

Not only am I dead, but so are lots of my friends.

I'm so glad you told us.

 

It's not generally a good idea to mix drugs, but most of the time you will get away with it.

Unless your liver is already shot and/ or you are taking lots of alcohol and/ or aspirin there's not a problem for a fit healthy person.

 

Acetaminophen (paracetamol for those on this side of the pond) is hepatotoxic, particularly in overdose. On the other hand, paracetamol based remedies for the after effects excess drinking are on the market and they don't carry a warning saying that you should make sure you are fully sober before you take them.

[Jule Bale]

The carboxylic acid functionality can receive hydrogen bonds from -OH groups of alcohols.

 

Can you explain that more simply? I'm sorry, I'm new to science. Is there a relationship between the polarity or molarity of the alcohol that make it easier/effient to dissolve the tablet?

[mississippichem]

Can you explain that more simply? I'm sorry, I'm new to science. Is there a relationship between the polarity or molarity of the alcohol that make it easier/effient to dissolve the tablet?

 

Hydrogen bonds are weak non-covalent bonds between hydrogen attached to an electronegative element and another electronegative element.

 

 

Here is acetylsalicyclic acid. The ester functional group and the carboxylic acid functional group are the groups on the side of the ring with the oxygens. Ethanol and Methanol have -OH groups and these groups have hydrogen bond interactions with acetylsalicyclic acid.

[Jule Bale]

Hydrogen bonds are weak non-covalent bonds between hydrogen attached to an electronegative element and another electronegative element.

 

 

Ahh!! Thank you so so so so much!! I get it now!

Here is acetylsalicyclic acid. The ester functional group and the carboxylic acid functional group are the groups on the side of the ring with the oxygens. Ethanol and Methanol have -OH groups and these groups have hydrogen bond interactions with acetylsalicyclic acid.

 

Hydrogen bonds are weak non-covalent bonds between hydrogen attached to an electronegative element and another electronegative element.

 

 

Here is acetylsalicyclic acid. The ester functional group and the carboxylic acid functional group are the groups on the side of the ring with the oxygens. Ethanol and Methanol have -OH groups and these groups have hydrogen bond interactions with acetylsalicyclic acid.

 

Ahhhh I get it now! Thank you SO SO much!