Comparative Analysis of Aspirin and Paracetamol

Currently, paracetamol is a first-line choice for pain management; those with osteoarthritis, simple headaches, and those with musculoskeletal conditions. With proper use, it is rare for paracetamol to have adverse affects.

Aspirin and paracetamol may have very different histories and development but share similar mechanisms within the body and their corresponding side effects. Although aspirin has many added benefits that paracetamol does not, paracetamol continues to be the most used pain relief within Australian households.

Hippocrates of Kos, the famous physician of ancient Greece, used extracts from the willow bark, called salicin, to reduce fevers and relieve pain. Salicin is formed of glucose and salicyl alcohol. Oxidation occurs to form acetylsalicylic acid from salicylic acid (Shepherd, Petherick, Martin 2019). Salicylic acid, the active part of the salicin molecule, reduces fever and relieves pain but also acts as an anti-inflammatory although it can be very irritating to the stomach (Shepherd, Petherick, Martin 2019).

Charles Frédéric Gerhardt first prepared acetylsalicylic acid; now Aspirin, forty years before Hoffman’s experiment. In acetylsalicylic acid, the acetyl group, replaces the H of the phenolic OH group of salicylic acid (Shepherd, Petherick, Martin 2019). Hofmann’s experiment, testing his father’s arthritis with acetylsalicylic acid, turned out to be successful and now the Bayer Company, in 1899, began to market powdered ‘Aspirin’. The name in combination of Acetyl and the Spir from Spiraea Ulmaria, the meadowsweet plant. Today, Aspirin is the most common drug for illness and injury and over 100 billion 50mg tablets are manufactured per year (ASPREE 2020).

Paracetamol’s history dates back to 1893. This was the first time it was clinically used. Unlike aspirin, paracetamol was discovered by accident when a similar molecule acetanilide was put to use as an analgesic and antipyretic medicine in the late 1800’s (PubChem 2016). Australia began using it commercially in 1956. Originally it was sold under the name ‘Triagesic’, but was removed as it was found to potentially cause blood damage but later that was proven wrong and it was brought back by Sterling-Winthrop Company as ‘Panadol; (Brune, Renner, Tiegs 2014). You could only retrieve it with a prescription up until 1959, then it became an over-the-counter medication. It is now considered a house hold drug and amongst the most popular drugs for injury and illness. (Informed Health 2016). Paracetamol is one of the most common drugs used in the world, and is manufactured in huge quantities.

Aspirin and Paracetamol serve many of the same purposes including the use for analgesic treatment to soothe headaches, toothaches, menstrual pain and rheumatoid arthritis (Szalay 2014). They also contain a atipyrecticc effect to help reduce fevers. Aspirin has added benefits including anti-coagulant and anti-inflammatory properties.

They have the same purposes due to their similar structure. Aspirin and paracetamol are recognised by the same enzyme. This enzyme is responsible for the biosynthesis of prostaglandins, which are involved in the dilation of blood vessels that causes pain experienced in a headache. Reduction of the amount of prostaglandin, therefore, helps and prevents headaches and other pain (Fitzgerald 2011).

Aspirin and paracetamol share similar side effects including headaches, heartburn, nausea and stomach discomfort. Aspirin has heavier side effects including diarrhoea, internal bleeding, black and bloody faeces and for children, risk of Reye’s syndrome is increased along with hives, facial swelling and difficulting breathing as a result of a severe allergic reaction. Paracetamol also shares heavy side effects if taken in excess or against the recommended use include bloody urine or faeces, ulcers, skin rashes, jaundice, unusual bleeding or bruising, or low grade fever with chills (study.com 2016). People who use it long term can form liver damage eventually causing liver failure or liver cirrhosis (Fitzgerald 2011).

Aspirin is more widely used by doctors and pharmacists as it not only helped fever and pain but has anticoagulant and anti inflammatory properties. Aspirin is useful to prevent atrial fibrillation, heart attack or stroke as it has blood thinning effects which reduce the blood from clotting easily within the blood vessel (Shepherd, Petherick, Martin 2019).

In a study (Seymour, R., Hawkesford, J., Sykes, J) comparing the pain relief strength of paracetamol and aspirin with the use of a placebo, it was shown that the aspirin had a much stronger effect on the patients after a period of 22-23 minutes.

Currently, paracetamol is a first-line choice for pain management; those with osteoarthritis, simple headaches, and those with musculoskeletal conditions. With proper use, it is rare for paracetamol to have adverse affects.

Aspirin and paracetamol may have very different histories and development but share similar mechanisms within the body and their corresponding side effects. Although aspirin has many added benefits that paracetamol does not, paracetamol continues to be the most used pain relief within Australian households.

Synthesis of Aspirin as a Widely Used Drug

Aspirin is a widely used drug which helps reduce fevers as well as reduce pain. It was originally just salicylic acid, which can be found naturally in the bark of willow trees. It is one of the oldest natural medicines used to treat fevers, illnesses as well as reduce pain. However, it was harsh on the stomach taking the acid by itself, which is why chemists in the 19th century began experimenting to find a softer version which does the same thing.

To create aspirin, salicylic acid is often mixed with an excess of an anhydride, which synthesises to create aspirin along with an acid.

Salicylic acid is converted to aspirin through the process of esterification. This esterification reaction occurs between the acid and the compounds containing a hydroxyl group and only takes place in acidic environments. Hence, the use of a concentrated acid is required.

The mixture is then heated gently, before being it is cooled to form crystals. Aspirin has very low solubility in cold water, so this process removes the soluble acids but not the aspirin. The aspirin is then purified by recrystallisation, where the impure crystals are dissolved in a small volume of hot ethanol. Water is then added, and the mixture is yet again cooled. The aspirin will recrystallise, and the unreacted salicylic acid remains dissolved in the solution. The liquid is filtered out using a Buchner funnel and the crystals left out to dry. To test the purity of the aspirin, a drop of low concentrated iron chloride is able to react with the product. It will change to a purple colour in the presence of salicylic acid and remain the same yellow colour in the presence of aspirin.

Lab Vs Industrial

In order to manufacture aspirin industrially, it is important to take in consideration of the cost of the synthesis and the physical properties of the materials involved (The Manufacture of Aspirin, n/a). There are two main ways to synthesise aspirin, using acetic anhydride or acetyl chloride. Both ways have its pros and cons, but there is an obvious preferred method. If you were to use 400kg of salicylic acid, you would need 200L of acetyl chloride or 400L of acetic anhydride.

It is much cheaper to be using acetic anhydride than acetyl chloride. The densities of the two materials are also very similar, making the price estimates pretty accurate of the actual cost.

As there will be the same amount of salicylic acid and toluene in both reactions, those prices can be ignored. Acetic anhydride will cost approximately $430, while acetyl chloride costs $3900.

In addition to this, the Material Safety Data Sheet reveals that acetyl chloride is very toxic and dangerous. It also produces hydrochloric acid in large quantities and has many undesirable properties, which is not wanted.

Synthesising aspirin in a lab is very much similar to industrial. Salicylic acid is reacted with an excess of acetic anhydride, or acetic acid, as that is less toxic than acetic anhydride and safer to use. The equipment used will be much simpler and less advanced than industrial production companies, but the method still has the same concepts in them.

Importance of Reaction

Aspirin is important because it is an anti-inflammatory drug and a common pain reliever for minor pains and also reduces fevers. Although new pain killers are now produced that are much more effective, aspirin can be used long-term in low doses to prevent blood clots, stroke and heart attacks.

Using Aspirin to Treat Coronary Heart Disease

Coronary artery disease is one of the most normal but dangerous disease in the world. It spreads widely because the huge morbidity. Coronary artery disease is always happen in people who are smoking, drinking too many alcohol, high blood pressure, high cholesterol, overweight, high stress in their life, and, family history. For the family history, if your parent, grandpa, grandma or even your ancestors have coronary artery disease, you may also have coronary artery disease. Coronary artery disease will make people get chest pain, some of the slight patient may not have a big effect of their normal life, such as walking, climping, but if the aggravated condition, normal life will be effect because of it. Patient can not do any of physical activity even normal walking can make patient dangerous. The breath of patient will become shortness because the blood is clotting, heart will also attract because of it.

Aspirin is one of the medicine that can treating coronary artery disease, it can help to prevent coronary arteries obstruction, and also prevent obstruction of the coronary arteries. It can intervenes with individual’s blood’s clotting action. When human are bleeding, platelets, a kind of cells that clotting blood will build up at the place of wound. The platelets help to build a things that can stop bleeding like a plug. The plug can close the opening in the blood vessel to stop bleeding. Aspirin prevents blood flow to the heart and causes a heart attack. That why aspirin therapy can reduces the clotting of platelets and prevent the heart attack.

Sometime, aspirin is not very suitable for the patient who have clotting or bleeding disorder or maybe they are already taking another blood thinner medicine. Some of the people will also be allergy to aspirin, also it may cause asthma. Because aspirin will reduces the clotting of platelets. Therefore, it is bleeding easily and difficult to stop the blood bleeding.

Although taking aspirin everyday can help prevent a clot-related stroke, it may increase the risk of a bleeding stroke. It will cause bleeding stomach ulcers and also having gastrointestinal bleeding. It will increases patient risk of developing a stomach ulcer. If patient have bleeding anywhere in the gastrointestinal tract, taking aspirin will cause it to bleed more, or even can threatening life. People that have already taking aspirin and need a surgical procedure, it will risk excessive bleeding during surgery. Remember to tell the doctor that you are taking aspirin everyday. Patient has already been taking aspirin for a long time, suddenly stop taking aspirin could have a rebound effect that may make a blood clot or also increase patient’s risk of heart attack.

In conclusion, aspirin is indeed a very effective drug for the treatment of coronary artery disease. Compared with other treatments, aspirin is cheaper and has the same effect as other treatments for coronary artery disease, but it is very cheap. Aspirin is a kind of drug which is technically perfect and widely used in the world. It also represents that aspirin is a relatively safe drug. Although there are still some shortcomings, but the probability of occurrence as long as you pay attention to some will basically not happen, even if it will, the probability of occurrence is very small.

Comparative Analysis of the Purity and Price Level of Different Aspirin Tablets

Background information

One of the most common drug used in our society is aspirin which was one of the first drugs to come into common usage.

What is aspirin?

Aspirin is a white crystalline powder with a melting point of 135 C. The common chemical name for aspirin is acetylsalicylic acid. Its systematic name is 2-(acetyloxy) benzoic acid. The chemical buy Cialis no prescription formula of aspirin is C9H8O4 and the atoms are arranged according to the following diagram

How was it discovered?

The ancient Egyptian made used of willow bark a plan which contain salicylic acid for aches and pain.

Salicylic acid is the key ingredient of aspirin but this was only discovered around the 18century when Edward stone discovered aspirin by showing how a preparation of willow bark powdered help 50 patients of ague. It was in the year 1874 that a scientist Hermann Kolbe discover synthetic salicylic acid but this was not easy to use since a when administered could easily course nausea and vomiting to a patient and sometime even bring him to a coma. To reduce this effect a buffer was need, this came out with the introduction of what is today known as aspirin by the chemist Felix Hoffman at Bayer in the year 1890 in the form of acetylsalicylic acid

How does aspirin work?

Damaged cell usually produce and enzymes called cyclooxygenase which produce a chemical called prostaglandin which send a message to the brain that a part of the body is in pain. Aspirin act as a non-steroidal anti-inflammatory drug, it directly act on the source of the pain and prevent the production of cyclooxygenase therefor reducing pain sensation. The problem with this is that cyclooxygenase is also known for producing mucus lining of the stomach so a common or daily used of aspirin will result to stomach ulcer and also since it is a weak acid it reduce stomach ph. to solve the fall in stomach ph a buffer is usually added to aspirin tablet.

Why is aspirin buffered?

A buffering agent, such as that contained in buffered aspirin, is used to preserve the pH of the aspirin as it is introduced to the patient 39;s stomach, which is very acidic. Acetylsalicylic acid

Introduction

Aspirin is one of the most common drug which is been used to solve pain problems over a countless number of different, it can also been used to reduce cancer risk and avoid heard attack. In my whole life I cannot remember of a day when I had pain problem and I was unable to find a tablet of aspirin, even when you are not searching for an aspirin tablet but for another drug your eyes will always enter in contact with an aspirin table so I slowly made the deduction that it was the most abundance and common drug in the world. My confusion with aspirin appeared when a day I took two different tablet of aspirin, I read what was written on the two and I did not understood the logic behind it. It was clearly written that the two were aspirin tablet but the brand name was different and they also had different price but, finally I decided to use the one with the greatest price following the logic that it cost more so has more effect but I could not bring exclude the fact that I have been using the drug for years and I must already have tested a great variety of aspirin tablet from different brand without knowing but I have never seen any different so my question was why does they have different price? To answer this question I came out with the idea that since aspirin also known as acetylsalicylic acid is the main component of all the tablet must come from the aspirin concentration in each table. My experiment will consist of a titration of different aspirin tablets to find out the concentration of aspirin in each and find out if the price different is justify.

With the use of sodium hydroxide and ethanol I will compare the purity and price level of of different aspirin tablets.

Reaction with sodium hydroxide

This is an acid-base reaction in which the acetylsalicylic acid reacts with the base sodium hydroxide to produce the salt sodium acetylsalicylate and water (acid + base → salt + water). … This is called the “end point” of the reaction. If one continues adding NaOH after the end point, the solution will turn dark red.

  • C₉H₈O₄+NaOH=C9H7O4Na
  • C₉H₈O₄+NaOH=C9H7O4Na+H2O

Why is ethanol used in the titration?

Ethanol is used in the titration to dissolve aspirin. It is then titrated against sodium hydroxide (base) using phenolphthalein as indicator. Ethanol has a hydrophobic carbon chain. In this sense, water can only dissolve the carboxylic acid and polar portion of aspirin but the methyl ester may not be properly dissolved. so as ethanol is used to speed up the reaction and to better dissolve the aspirin. Acetylsalicylic acid is slightly soluble in water, with a limit of solubility reported as approximately 3 mg/ml at 25 Deg C.It is also soluble in ethanol at 50 mg/ml. so it is more soluble in ethanol than in water.

Experiment

Variables independent Initial and final burets reading dependent Purity level Depend on the mass of aspirin present and mass the tablet. control Mole of NaOH 0.1mole AIM: measuring the concentration of aspirin in tablet of different brand

Materials

  • 0.100 M of NaoH, Ethyl alcohol, various aspirin tablets,150 ml flask, a burets ,mortar and pestle phenolphthalein indicator and goggles

Procedure

  • Find the mass of different aspirin tablet, then grind each of them in a fine powder using mortar and pestle.
  • Tare a piece of weighing paper on the balance. Carefully transfer as much powdered sample to the paper and find the mass.
  • Place the powdered sample in a 150ml beaker.
  • Add a 10.0ml portion of ethyl alcohol to the beaker and stir.
  • Add 25.0ml of water to the beaker.

Put 3 drops of the phenolphthalein indicator in your flask. Put a magnetic stir bar in your flask and place the flask on the center of the stir plate

The burette is filled with 0.100M of NaOH and record the initial volume on the burette. There must be no bubbles apparent in the burette.

Begin titrating. Add the NaOH in 1.0ml increment, making note of the color change occurrence. Continue adding base 5.0ml and past the equivalent point, this is when the solution turn pink due to the phenolphthalein.

Repeat the step for all aspirin tablet.

Data and calculation

  • Below is a diagram of the chemical equation that show the reaction between aspirin and sodium hydroxide.

First tablet

  1. Aspirin brands Mass in grams First trial cm3
  2. Second trial cm3
  3. Third trial cm3
  4. Average in cm3 price
  5. Aspirin cardio 5.6 5.1 5.4 5.4 5.3 6300fcfa
  6. Mass of a tablet= 5.2 g
  7. Concentration of sodium hydroxide= 0.100mol/dm3
  8. Volume of sodium hydroxide needed to neutralize it=5.3 cm3
  9. Number of mole of NaOH (5.3〖cm〗^3)/1000×0.100mol/〖dm〗^3 =0.00053moles
  10. If 1 mole of aspirin neutralize 1 mole of NaOH
  11. Aspirin has a chemical formulae of C9H8O4 and a relative molecular mass of 180.2 grams.
  12. So 0.00053 mole of aspirin neutralize 0.00053 mole of NaOH 1 mole of aspirin has a mass of 180.2
  13. A pure tablet will have 5.6/180.2= 0.03108 moles
  14. The Purity of aspirin is obtain by (Actual moles)/( possible moles )→0.00053/( 0.03108)=0.01705
  15. To change this answer into percentage, multiply it by 100. This will give 1.705%.
  16. That is 1.705% pure, this mean that this tablet is compose at only 1.705% of aspirin.

Second tablet

  1. Aspirin brands Mass in grams First trial cm3
  2. Second trial cm3
  3. Third trial cm3 average in cm3 price 1.03 5.7 5.5 5.3 5.5 850fcfa
  4. Mole of NaOH used is (5.5×0.100)/1000=0.00055mole
  5. Possible mass 1.03/180.2=0.00572mole
  6. Purity of aspirin 0.00055/0.00572=0.0962
  7. Multiply it by 100 to change it to percentage
  8. That is 9.62% purity

Third tablet

  1. Aspirin brands Mass in grams First trial cm3
  2. Second trial cm3
  3. Third trial cm3 Average in cm3 price 4.64 5.3 5.4 5.6 5.4 5200fcfa
  4. Mole of NaOH used is (5.4×0.100)/1000=0.00054mole
  5. Possible mass 4.64/180.2=0.02576mole
  6. Purity of aspirin 0.00054/0.02579=0.0209
  7. Multiply it by 100 to change it to percentage
  8. That is 2.09% pure

Analyses

  • Quantity or mass of aspirin found in each table (%purity)/100×mass of table
  • For the first tablet=1.71/100×5.6grams=0.957grams
  • Aspirin brand % purity Mass of aspirin present Price in fcfa
  • First tablet 1.71 95.7mg 6300
  • Second tablet 9.61 99mg 950
  • Third tablet 2.09 97mg 5200
  • The uncertainty of the values is obtain with the formula range/2
  • Uncertainty of first titration=(5.4-5.1)/2=0.15
  • Uncertainty of second titration=(5.7-5.3)/2=0.2
  • Uncertainty of third titration=(5.6-5.3)/2=0.15
  • Uncertainty of the experiment (prescribe mass-mass obtain in experiment)/(prescribe mass)×100
  • For the first titration (100-95.7)/100*100=4.3%
  • For the second titration, the uncertainty is 1%
  • For the third titration, the uncertainty is 3%

Conclusion

They all have about 100mg of aspirin in them but they have different purity level due to different in mass. The tablet with the highest price has the lowest purity level and the one with the lowest price has the highest purity level. Therefore aspirin purity and price are inversely proportional. This is because has side effect on the stomach so usually aspirin tablet are coated or buffered. Buffered aspirin, combines an antacid such as calcium carbonate (found in Tums) or aluminum hydroxide (found in Maalox) with aspirin.so the higher the buffer solution the lower the effect of aspirin on the stomach therefor one tablet of 1.7% purity has less side effect than one with 9% despite they contain about 100mg of aspirin.

References

  1. Essay on Determination of Asa Content of Aspirin – 2438 Words. (n.d.). Retrieved from https://www.studymode.com/essays/Determination-Of-Asa-Content-Of-Aspirin-1946782.html
  2. Acetylsalicylic Acid. (n.d.). Retrieved from https://www.sciencedirect.com/topics/chemistry/acetylsalicylic-acid

Analytical Essay on Aspirin: History, Types of Use and Benefits

Introduction

Aspirin is a widely used drug worldwide, and it is regarded as one of the most important achievements in pharmacy and medicine in the 20th century. medical historians have traced the birth of pharmaceutical aspirin to 1897, it dates to approximately 3500years back when willow bark was used as a painkiller and an antipyretic by the early Sumerians and Egyptians and then in Greece and Rome by the physicians. In modern medicine aspirin has had precursors like salicylates in the 17th century, then in 1897 a bayer chemist first synthesized aspirin and about 70 years later a pharmacologist john vane expatiated its mechanism of action in inhibiting prostaglandin production [1]. Aspirin is a non-steroidal anti-inflammatory drug and was originally used as an antipyretic and an anti-inflammatory drug then it became popular and was used for its antiplatelet properties which is useful in preventing cardiovascular and cerebrovascular diseases, it in recent developments could be used in cancer chemoprevention [2], in recent years newer uses for aspirin are getting researched some progress has been seen in the possible reduction in pre-eclampsia, dementia, cataracts and some types of cancer, and because of aspirin’s various uses and benefits its been called the miracle drug in recent years [3].

The synthesis of aspirin (Fig.1)

To prepare aspirin, salicylic acid is reacted with acetic anhydride which is in excess see(fig.1)with a little amount of acid catalyst used, and the excess acetic anhydride would be quelled by the addition of water, the aspirin product obtained is not very soluble in water and would precipitate when water is added, but acetic acid is very soluble in water so it is easily separated from the aspirin product. The aspirin obtained after the reaction is called the crude product and can be purified by its recrystallization in hot ethanol.[4]

In this experiment, aspirin would be synthesized by reacting salicylic acid with acetic anhydride in the presence of phosphoric acid and after synthesis, the product would be purified by recrystallization of the sample. Then the purity would be tested by various chemical tests and by analysis by usage of a TLC (thin layer chromatography).

Experimental

Refer to the laboratory manual [5]

Results and discussion

In this experiment into the synthesis of aspirin, the product recovered from the reaction is not pure so after recrystallization, it should be as pure as its pharmaceutical equivalent assuming the procedure was carried out as it should have.

Table 1: mass of salicylic acid and crude aspirin

  1. Mass of salicylic acid
  • 5.00 g
  1. Weight of watch glass and crude aspirin
  • 35.16 g
  1. Weight of watch glass
  • 28.49 g
  1. Mass of crude aspirin
  • 6.67 g

In the table 1 above the mass of the crude aspirin obtained from the experiment is obtained from weighing by difference the weight of the watch glass and aspirin and the weight of the watch glass, the result obtained by this might not be accurate due to the fact that a series of errors occurred, such as when the product was transferred some was spilled and all the product was not completely collected after the experiment was completed and also the inaccurate weighing of the watch glass before the aspirin was added, all these could contribute to the inaccuracy of the values obtained.

The purpose of recrystallization is to purify the aspirin, recrystallization is a separation technique in the solid is dissolved in a hot liquid until there is saturation then the mixture is then allowed to cool and then form crystals, during the recrystallization in the lab the crystals didn’t form while cooling so a glass rod was used to scratch the sides of the beaker this was done to stimulate crystal formation by giving the crystals something to form round which sped up the formation of the crystals.

Table 2: mass of purified aspirin

  1. Weight of watch glass and purified aspirin
  • 30.74 g
  1. Weight of watch glass
  • 26.38 g
  1. Mass of purified aspirin
  • 3.91g

After the recrystallization of the crude aspirin was successfully completed the mass of purified aspirin was recorded, as seen in the table above. During the recrystallization process, a sizeable amount of product is lost due to inefficient lab procedures so the mass of the purified aspirin may not be accurate.

For the ferric chloride test to work, a complex must be formed between an electronegative oxygen atom and electropositive iron atom. Ferric chloride reacts with the phenol group to cause a colour change. The melting point of the products were determined using the melting point apparatus, small samples of the products were placed in the apparatus then was watched until they each melted, and the points were recorded. The melting points of the salicylic acid, crude aspirin, and purified aspirin and compared to the literature values which were gotten from the Merck index[6]. The recrystallized product should be higher than the crude aspirin but both were lower than the literature due to impurities mainly due to the solvent in the recrystallized and also left over in the crude product, but the lower melting point might be also due to human error when reading the temperatures off the melting point apparatus.

Table 3: melting points of salicylic acid, crude and purified aspirin.

Melting point

  1. Salicylic acid
  • 159°c – 152°c
  1. Salicylic acid (literature)
  • 157°c – 159°c
  1. Crude aspirin
  • 97°c – 118°c
  1. Purified aspirin
  • 128°c – 130°c
  1. Aspirin (literature)
  • 135°c

(fig 2.)

After the recrystallization was completed and the melting points were recorded the samples underwent some chemical tests to indicate the purity of the crude and recrystallized aspirin and then the results were compared to the starting material in the synthesis, salicylic acid. The test reagent used was ferric chloride FeCl3 solution and this gave a highly coloured complex when reacted with phenols so for a standard we performed the ferric chloride test against phenol itself. To perform the test 5mL of water was added to each of the test tubes containing the crude aspirin and recrystallized aspirin samples and 5mL solutions of the salicylic acid and phenol were made in two further test tubes and then 10 drops of 1% FeCl3 solution and then colour changes were observed and recorded.

Table 4: chemical tests

  • Substance
  • Initial colour of aqueous solution
  • Colour after adding the fecl3 solution
  • Phenol
  • Colourless
  • Dark purple
  • Salicylic acid
  • Solution with white percipitate
  • Very dark purple
  • Crude aspirin
  • Whitish gel with percipitate
  • Light purple
  • Recrystallized aspirin
  • White solution with percipitate
  • Purple

FeCl3 reacts with phenol groups so a purple complex, forms with both phenol and salicylic acid, however aspirin does not contain a phenol and therefore it should not react, the phenol must be converted to an ester and change colour.

To calculate the percentage yield of the recrystallized aspirin obtained the actual yield is divided by the theoretical yield then the percentage was taken, firstly the moles of salicylic acid was calculated by dividing the mass of the salicylic acid used by the molecular mass then the number of moles of salicylic acid calculated was multiplied by the molecular mass of aspirin to give the theoretical yield which is now divided by the actual yield and multiplied by a hundred to give the percentage yield.

  • Percentage yield = Actual yield/ theoretical yield X 100
  • Number of moles of Salicylic acid= mass/GFM = 5.00/142 = 0.00352
  • Moles of salicylic acid x GFM of aspirin = 0.0352 x 180 = 6.33g
  • (3.91/6.34) x 100 = 61.67%

The yield that was obtained is less than 100% due to the loss of recrystallized product during the experiment and inefficient lab skills in weighing and basic lab procedures.

BP Assay for aspirin

In a flask with a stopper 1g was dissolved in 10mL of ethanol and 50mL of 0.5 NaOH then was closed and allowed to stand for an hour, this was done in duplicates and in a third flask, ethanol was measured, and NaOH without aspirin and then also allowed to sit for an hour, after the hour elapsed 0.2mL of phenolphthalein indicator was used to titrate 0.5M HCl. This assay is a back titration which involves the addition of an excess of NaOH to the sample followed by the titration with HCl to determine the amount of excess so the amount of base equivalent to the sample is calculated but NaOH reacts with the CO2 in the atmosphere so the exact amount of NaOH has to be calculated by performing a blank titration.[7]

Table 5: mass of each sample of recrystallized aspirin taken

  • Sample 1
  1. Mass of weighing bottle + aspirin
  • 13.46g
  1. Mass of weighing bottle
  • 12.42g
  1. Mass of aspirin taken
  • 1.04g
  • Sample 2
  1. Mass of weighing bottle + aspirin
  • 13.42g
  1. Mass of weighing bottle
  • 12.44g
  1. Mass of aspirin taken
  • 0.98g

Table 6: burette readings

  1. Sample 1
  • Final burette reading
  1. 29.40 cm3
  • Initial burette reading
  1. 0.00 cm3
  • Titre
  1. 29.40 cm3
  2. Sample 2
  • Final burette reading
  1. 31.40 cm3
  • Initial burette reading
  1. 0.00 cm3
  • Titre
  1. 31.40 cm3
  • Blank
  • Titre
  1. 49.30 cm3

Calculations

Some calculations were performed after the BP assay had been completed in order to test for the purity of the recrystallized products, these calculations were done on the two samples collected and can be seen below.

  1. Number of moles of aspirin = [(b-a) x molarity of HCl x 0.5]/ 1000
  2. Mass of aspirin = number of moles x molar mass of aspirin
  3. Percentage purity = mass calculated/mass taken x 100%

First sample:

  1. Number of moles of aspirin = [(49.30 – 29.40) x 0.5 x0.5]/1000 = 0.004975moles.
  2. Mass of aspirin = 0.004975 x 180.2 = 0.896g.
  3. %purity = 0.896/1.04 x 100 = 86.5%

Second sample:

  1. Number of moles of aspirin = [(49.30 – 31.40) x 0.5 x0.5]/ 1000 = 0.004475moles.
  2. Mass of aspirin = 0.004475 x 180.2 = 0.806g
  3. %purity = 0.806/0.98 x 100 = 82.24%

Although the two samples had high percentage purities they can not be acceptable because for a sample to be considered pure it must have a percentage purity of not less than 99.5% and no more than 101%, so none of the samples are acceptable because the experiment was only repeated twice further replication would have reduced the uncertainty in the results as well as making the experiment more reliable.

Another way of determining the purity of a substance is by thin layer chromatography. For this experiment during the one hour standing time for the BP assay a TLC analysis was performed on the synthesised aspirin also on the references of salicylic acid and pure aspirin, then it was visualised with ultraviolet light and then sprayed with ferric chloride solution.

(Fig 3.)

After the TLC analysis was completed and placed under the ultraviolet light the RF values were calculated as seen below;

  1. RF values = aspirin (A) = 0.5
  2. Salicylic acid (S.A) = 0.59
  3. Pure aspirin (P.A) = 0.48

When reacted with the ferric chloride solution a black spot appeared on the S.A spot and did not appear on the rest of the spots, this indicates that the sample of the synthesised aspirin is as pure as the pure sample of aspirin as it was also unreacted and also was around the same distance travelled on the solvent front so this also proves that the synthesised aspirin can be regarded as pure. [8]

Conclusions

For this experiment , the actual yield of aspirin was 3.91g but given that the theoretical yield for the experiment was 6.34g , the percentage yield of the aspirin was 61.67%, the percentage yield was slightly low due to the fact that a part of the product was lost. Also the Rf values of the recrystallised aspirin, salicylic acid, and pure aspirin were 0.5,0.59 and 0.48 respectively , furthermore from the TLC analysis we can conclude that the salicylic acid travelled the furthest as it is the least polar amongst all the samples as displayed by the Rf values. A consensus of all the tests performed show that the recrystallised product although of acceptable yield is not regarded as clinically pure so to prevent error in the future , a number of steps could be taken including ensuring that the water bath is sufficiently heated and also conducting the experiment under a fume cupboard to avoid exposure to atmospheric air along with better lab procedures and techniques. [9]

References

  1. Maria M, Sergio M, Raffaele C. the first 3500 years of aspirin history from its roots. vascular pharmacology. 2019; 113: 1-8.
  2. Peter E, Michael S. New uses for old drugs: aspirin the first miracle drug. The pharmaceutical journal.2001.
  3. Sarah M, Brian F. Aspirin. reference module in biomedical sciences.2018.
  4. Lewis. Aspirin: a curriculum resource for post-16th century chemistry courses. 2nd edition. Royal society of chemistry. london.2003.
  5. The laboratory manual. The Robert Gordon university. Synthesis of aspirin. 2019 [accessed November 17th ,2019].
  6. Maryadele J O’Niel. The merck index. 13th edition. Cambridge; royal society of chemistry, 2013.
  7. British Pharmacopeia Commission. British Pharmacopeia 2011. London: TSO; 2011.
  8. Williamson K, Masters K. macroscale and microscale organic experiments. 6th edition, cengage learning. Belmont, 2011.
  9. Marian E. the synthesis and analysis of aspirin. Journal of chemical education. 2014.

History, Components and Properties of Aspirin: Analytical Essay

Abstract

Aspirin, a medicine that dates back to the times of ancient Sumeria and Egypt, has played a vital role in helping with inflammation and pain. Felix Hoffman is responsible for what we know aspirin is today. At first, it was salicylic acid, and it was too harsh on the stomach to be taken. Felix modified the hydroxy group and this allowed it to not cause people’s stomachs to get upset. In modern times aspirin is not just used for pain and inflammation relief. Aspirin can be beneficial in the prevention of heart disease. Aspirin is one of the oldest pain and inflammation-reducing medicines. Aspirin is categorized as a nonsteroidal, anti-inflammatory drug. This family of drugs also includes ibuprofen. The nonsteroidal anti-inflammatory drugs prostaglandins from being produced by the cyclooxygenase enzymes. Prostaglandins have many important functions. They are responsible for inflammation, which is important for healing but also causes pain and fever. Although aspirin has many benefits such as pain inflammation and fever, the risks cannot be simply overlooked. Aspirin can be very harmful if not taken correctly or if taken on a daily schedule.

Aspirin has a long history dating back more than 2000 years ago. A synthetic substance derived from salicylic acid which is found naturally occurring in the bark of the willow tree, aspirin has many positive uses for patients with a number of different ailments. Along with the positive uses of aspirin, there are also risks and dangers, and side effects. Aspirin is part of the non-steroidal anti-inflammatory (NSAID) family of drugs that has been studied and researched many times over.

History of aspirin

From as early as 1500 BC, willow was being utilized for medicinal purposes by ancient civilizations such as the Sumerians and the Egyptians. Sometime around 400 BC, Hippocrates used willow leaf tea to help women and the pain experienced in childbirth. Fast forward to 1763. The Royal Society released a report containing the specifics of a five-year study of the use of the willow bark in powered form that was able to cure a fever. In 1828, Joseph Buchner was successful in the extraction of the active ingredient from willow. He named the substance salicin. Charles Frederic Gerhardt found that he was able to change the components the salicylic acid because he introduced an acetyl group in place of a hydroxyl group. His changes made him one of the first to develop aspirin, but this new compound was very unstable and prevented him from developing it any further (Goldberg, 2009). Felix Hofmann has also been accredited for the development of aspirin as it known today. Arthur Eichengrün, the manager of chemical research at Bayer, assigned Felix to innovate aspirin. He took this task personally since his father was suffering from rheumatism and couldn’t ingest the salicylic acid without throwing up. He altered the salicylic acid chemically by modifying the hydroxyl group on the benzine ring. This allowed aspirin to be absorbed without intense gastrointestinal distress. After the stomach processed the new molecule, it converted back to salicylic acid. This provided the medical benefits of aspirin (Connelly, 2014).

The components and properties of aspirin

The chemical name for aspirin is acetylsalicylic acid. It is an odorless, colorless or white, crystalline powder that has a bitter taste. Aspirin melts at a point of 275°, while the boiling point is 284°. Its density is 1.4g/cm³ and its molecular weight is 180.16 g/mol. Aspirin is created by combining salicylic acid and acetic acid. The chemical formula for salicylic acid is C7H6O3, and the chemical formula for acetic acid is CH3COOH. C9H8O4 is the chemical formula for acetylsalicylic acid, so it contains nine carbons to eight hydrogens to four oxygens, at that ratio. Aspirin also has 3 functional groups within the compound, which are the carboxylic acid group, ester group, and the aromatic group, also known as a benzene ring. The groups work together to form the compound and give it the characteristics that aspirin has (Baarnseweg & Dijk, 1990).

How aspirin works

Aspirin acts as an acetylating agent. Therefore, it inactivates cyclooxygenase and reduces the production of prostaglandin. Prostaglandin is a hormone-like substance that is produced on sites of damage or infection in the human body. The prostaglandins cause inflammation, fever, and pain. This only happens because of aspirin’s acetyl group. It bonds to Ser529 at the active site of the cyclooxygenase enzyme. Ser529 plays an important role in immune and inflammatory responses. As aspirin interacts with Arg120, it blocks access of arachidonic acid to the hydrophobic channel to Tyr385. The arg120 is found at the beginning of the hydrophobic channel, which is where prostaglandin is synthesized. Therefore, aspirin stops the production of prostaglandin (Mekaj, Daci, & Mekaj, 2015).

Within in the human body, aspirin is absorbed with expedience in the stomach and intestine by means passive diffusion. Passive diffusion is the movement of molecules across a membrane without the need of energy. It requires no energy because it is moving from an area of high concentration to low concentration. In the case of aspirin, the membrane is the stomach lining and the lining of the intestine. Aspirin is converted into salicylate acid in the stomach, in the blood, in the intestinal mucosa, and mostly in the liver. Salicylate is the anti-inflammatory and pain-reducing agent of aspirin. Salicylate then spreads throughout the body at a rapid rate. It attaches to albumin in the plasma. Albumin is a protein within the plasma that transports fatty acids, hormones, and other compounds. Aspirin is mainly metabolized in by the liver and it occurs by hepatic conjunction with glycine or glucuronic acid. Glycine helps prevent the unpleasant side effects of aspirin. The conjunction with glycine occurs most often. in cases of low-dose aspirin use, it is estimated that 90% salicylate metabolism happens through the glycine pathway. The salicylate the human body does not use is secreted through urination. This accounts for 10% of the complete elimination of salicylate in the body (Aspirin Pharmacokinetics, n.d).

The benefits of aspirin

Aspirin has many medical benefits. The drug can be used to combat mild to moderate pain. This is helpful with things like headaches, toothaches, and menstrual cramping. Aspirin can also be used to fight cold and flu-like symptoms. Aspirin fights these symptoms by reducing fever, which benefits able to feeling better. Additionally, aspirin is beneficial as an inflammation reducer (“Aspirin for Pain Relief”, 2018). Acute Inflammation is good; it is the body’s natural defense and it encourages healing. On the other hand, when the inflammation is chronic, it can damage the body instead of healing it. So, in cases of chronic inflammation aspirin can be very advantageous (Hobson, 2017).

One of the main benefits of aspirin is the prevention of cardiovascular disease and reducing the risks of heart attack and stroke with high-risk patients. Aspirin can reduce myocardial infarctions, strokes, and heart attacks by around 25% regardless of the age and sex of the high-risk patients. High-risk patients are identified by several factors: high blood pressure, high cholesterol, whether or not her or she smokes, the patient’s age, and their family history (Szczeklik, 2006).

The risks of aspirin

Although aspirin can be very benefit able, the health risk cannot be overlooked. First of all, the preventative qualities related to cardiovascular disease can cause a bleeding stroke because of the thinning of the blood. Another major risk of is gastrointestinal bleeding. It causes gastrointestinal bleeding because it blocks all the helpful substances that protect the stomach lining. As a result, it causes an upset stomach and bleeding in the stomach and intestine. The bleeding can get extremely serious and could cause hospitalization, with a blood transfusion. Allergic reactions can also occur with taking any amount of aspirin. An aspirin allergic reaction can be very serious. The symptoms include itchy rashes, flushing or blushing, and blocked nose, and asthma. Asthma can be very severe and cause an asthma attack, which could cause death (Whiteman, 2015).

Aspirin continues to be one of the most popular drugs in the world. With its properties that aide in reducing pain, fever, and inflammation, aspirin additionally helps to reduce the risk of heart attacks in some people. The chemical properties of aspirin make it a versatile drug that is affordable and effective for many ailments. From its beginnings in the willow tree, aspirin has developed into a drug that has withstood time and some controversy.

References

  1. ASPIRIN PHARMACOKINETICS. (n.d.). Retrieved from https://sepia2.unil.ch/pharmacology/index.php?id=83
  2. Connelly, D. (26 September 2014). History of aspirin. The Pharmaceutical Journal. Retrieved April 3, 2019.
  3. Goldberg, D. R. (2009, Summer). Aspirin turn of a century miracle drug. Distillations.
  4. Hobson, K. (2017, July 21). Is inflammation bad for you or good for you? Retrieved April 3, 2019, from https://www.npr.org/
  5. Mekaj, Y. H., Daci, F.T., & Mekaj, A. Y. (2015). New insights into the mechanisms of action of aspirin and its use in the prevention and treatment of arterial and venous thromboembolism. Therapuetics and clinical risk management, 11, 1449-1456. Doi:10.214/TCRM.S92222
  6. Should you take a daily aspirin for your heart? (2019, January 09). Retrieved April 3, 2019, from https://www.mayoclinic.org/diseases-conditions/heart-disease/in-depth/daily-aspirin-therapy/art-20046797
  7. Szczeklik, A. (n.d.). The History of Aspirin: The Discoveries That Changed Contemporary Medicine. Retrieved from http://www.pas.va/content/dam/accademia/pdf/acta18.pdf
  8. Whiteman, H. (2015, October 29). Aspirin: is it really a ‘wonder drug’? Retrieved from https://www.medicalnewstoday.com/articles/301766.php