Khushi Posted December 12, 2005 Share Posted December 12, 2005 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" Link to comment Share on other sites More sharing options...
RyanJ Posted December 13, 2005 Share Posted December 13, 2005 It is soluable in water < 0.1 g/100 mL at 23 Degrees C Source: http://chemfinder.cambridgesoft.com/ Cheers, Ryan Jones Link to comment Share on other sites More sharing options...
akcapr Posted December 13, 2005 Share Posted December 13, 2005 ryan there was no point to that post- he already knew it was slightly soluable . gosh Link to comment Share on other sites More sharing options...
Khushi Posted December 13, 2005 Author Share Posted December 13, 2005 *she ...lol i wanted to know how to determine the polarity of Acetylsalicylic Acid Link to comment Share on other sites More sharing options...
akcapr Posted December 13, 2005 Share Posted December 13, 2005 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. Link to comment Share on other sites More sharing options...
Ilja Posted December 13, 2005 Share Posted December 13, 2005 Try to solve it in Ethanol (C2H5OH) i think it will work better than if u do it with water. Link to comment Share on other sites More sharing options...
RyanJ Posted December 13, 2005 Share Posted December 13, 2005 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 Link to comment Share on other sites More sharing options...
YT2095 Posted December 13, 2005 Share Posted December 13, 2005 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). Link to comment Share on other sites More sharing options...
jdurg Posted December 13, 2005 Share Posted December 13, 2005 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. Link to comment Share on other sites More sharing options...
RyanJ Posted December 13, 2005 Share Posted December 13, 2005 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 Link to comment Share on other sites More sharing options...
warut Posted December 14, 2005 Share Posted December 14, 2005 What are those hepatotoxic compounds? Link to comment Share on other sites More sharing options...
RyanJ Posted December 14, 2005 Share Posted December 14, 2005 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 Link to comment Share on other sites More sharing options...
jdurg Posted December 14, 2005 Share Posted December 14, 2005 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. Link to comment Share on other sites More sharing options...
warut Posted December 14, 2005 Share Posted December 14, 2005 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. Link to comment Share on other sites More sharing options...
Khushi Posted December 15, 2005 Author Share Posted December 15, 2005 thanks....this is all really helping:) Link to comment Share on other sites More sharing options...
Jule Bale Posted January 20, 2011 Share Posted January 20, 2011 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 Link to comment Share on other sites More sharing options...
mississippichem Posted January 20, 2011 Share Posted January 20, 2011 Why? I'm just curious The carboxylic acid functionality can receive hydrogen bonds from -OH groups of alcohols. Link to comment Share on other sites More sharing options...
John Cuthber Posted January 20, 2011 Share Posted January 20, 2011 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. Link to comment Share on other sites More sharing options...
Jule Bale Posted January 20, 2011 Share Posted January 20, 2011 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? Link to comment Share on other sites More sharing options...
mississippichem Posted January 21, 2011 Share Posted January 21, 2011 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. Link to comment Share on other sites More sharing options...
Jule Bale Posted January 21, 2011 Share Posted January 21, 2011 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! Link to comment Share on other sites More sharing options...
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