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SYNTHESIS OF ACETYLSALICYLIC ACID

Ong, H.C.
1
, Padilla, B.G.
1
, Paglinawan, F.M.
1
, Pascual R.D.
1
, Pleos J.F.
1
University of Santo Tomas, Faculty of Pharmacy

ABSTRACT
Acetylsalicylic acid, much more known to the public as Aspirin, has been the well known analgesic and antipyretic, but most of us
dont know what the system behind the acetylsalicylic acid is. They act by blocking the synthesis of prostaglandins by inhibi ting
cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. But for us Pharmacy
students, it is not enough to know the system or mechanism behind the aspirin, but as well on how to synthesize it. It requires
saliculic acid, acetic anhydride and sulfuric acid. 2.00g of salicylic acid was tared in a watch glass, transferred into a test tube,
afterwards, a 5.00 ml of acetic anhydride was dispensed to the test tube and 5 drops of concentrated sulfuric acid was added. It was
then subjected to a water bath with occasional stirring. 20 ml of cold water was added and also subjected to ice bath to allow
crystallization. Then the solution was filtered and dried and afterwards, weighed.


BACKGROUND
Acetylsalicylic acid is also known as aspirin, 2-
acetoxybenzoic acid, ecotrin, acylpyrin,
polopiryna, and acenterine.
[1]
Its molecular
formula is C
9
H
8
O
4
and its melting point is 136 C.
It is a white crystal, commonly tubular or needle-
like, or white crystalling powder; odorless or has
a faint odor. It is stable in dry air; in moist air it
gradually hydrolyses to salicylic acid and acetic
acid. Slightly soluble in water (1:300), freely
soluble in alcohol (1:5). It must be stored in
airtight containers.
[2]

Aspirin is an anti-inflammatory agents that
are non-steroidal in nature. In addition to anti-
inflammatory actions, they have analgesic,
antipyretic, and platelet-inhibitory actions. They
act by blocking the synthesis of prostaglandins by
inhibiting cyclooxygenase, which converts
arachidonic acid to cyclic endoperoxides,
precursors of prostaglandins.
[3]
Inhibition of
prostaglandin synthesis accounts for their
analgesic, antipyretic, and platelet-inhibitory
actions; other mechanisms may contribute to
their anti-inflammatory effects. It is an
antipyretic which reduces fever.
Aspirin is a cyclooxygenase Inhibitors which
binds with cyclooxygenase (prostaglandin-
endoperoxide synthases) and thereby prevent its
substrate-enzyme combination with arachidonic
acid and the formation of eicosanoids,
prostaglandins, and thromboxanes.
[4]
It is also
used as fibrinolytic agent which convert
plasminogen to fibrinolysin. Aspirin is a platelet
aggregation inhibitors which antagonize or impair
any mechanism leading to blood platelet
aggregation, whether during the phases of
activation and shape change or following the
dense-granule release reaction and stimulation of
the prostaglandin-thromboxane system.
Figure 1. Chemical Structure of Acetylsalicylic
Acid

EXPERIMENTAL
A. Materials
The materials used in synthesizing aspirin
were the hard glass test tube, a 10 ml graduated
cylinder, dropping pipettes, 150 and 250 ml
beakers, a thermometer, stirring rods, filter
paper and a funnel.
The reagents used for synthesis of aspirin
were salicylic acid, acetic anhydride and
concentrated sulfuric acid. While the ones used
for the tests for purity were 2% aqueous Ferric
Chloride and Iodine. Commercially prepared
aspirin, benzoic acid, and benzyl alcohol were
also used for the comparison of the reactions for
the purity test of aspirin.

B. Method
First, 2.00 g salicylic acid was tared in a
watch glass and it was transferred in a clean, dry
20-cm test tube. Exactly 5.00 ml acetic
anhydride was dispensed to the test tube and 5
drops of concentrated sulfuric acid was added.
The test tube was then subjected to a water bath
on the hot plate with the temperature of 70-80 C
for 20-30 minutes with occasional stirring. The
mixture is stirred using a stirring rod until the
salicylic acid was dissolved. A drop wise of room
temperature water was added until the solution
became cloudy. The solution filled test tube was
then removed from the water bath. The inner
part of the test tube were scratched and rinsed
with cold water. After the rinsing the solution was
transferred to a 150 ml beaker. 20 ml of cold
water was then added to the rinsing filled 150 ml
beaker and was stirred occasionally. The beaker
was then subjected to an ice bath for 10 minutes
to allow the aspirin to crystallize. Then the
solution was filtered in a pre-weighed filter paper
and allowed to dry to get the aspirin samples
from the experiment. The aspirin synthesized
from the experiment was then weighed.
To test the purity of the synthesized aspirin,
the ferric chloride test for salicylic acid was used.
1 ml water was placed in 6 10-cm test tubes. A
corn grain amount of each sample was added in
every test tube. On the first test tube Salicylic
acid was placed, powdered commercial aspirin in
the second test tube, synthesized aspirin in the
third test tube, benzoic acid in the fourth test
tube and 1 ml of benzyl alcohol in the fifth test
tube. The sixth test tube filled with 1 ml water
was the control used. The sample used was
dissolved in 1 ml water then a drop of 2%
aqueous solution of ferric chloride was added.
The colors observed from the test tubes were
then noted.
The starch test was also done to test the purity of
the sample. 2 ml of distilled water was place in 3
test tubes. On the first test tube the prepared
aspirin was placed, and on the second the
commercially prepared, and on the last test tube
was the control used. On each test tube 1 drop of
iodine was added. The observed color on each
test tube was noted.
Also, for the purity test, a test for the melting
point was done. The samples namely the
prepared aspirin, the commercially available one
and the control sample were triturated and was
placed in a capillary tube. Then, each capillary
tube was bundled with the thermometer. It was
then subjected to an oil bath. After the samples
melted, the temperature was noted and was
listed for their corresponding melting points.

RESULTS AND DISCUSSION


REFERENCES
Books:
[1] United States Pharmacopeia and National
Formulary (USP 30-NF 25). Vol 2.
Rockville, MD: United States
Pharmacopeia Convention; 2007:1553-
1554.
[2] Parfitt, K., & Martindale, W. Martindale: The
complete drug reference. 36
th
ed. London,
UK: Pharmaceutical Press.
[3] Alldredge BK, Corelli RL, Ernst ME, et al, eds.
Applied Therapeutics: The Clinical Use of
Drugs. 10th ed. Philadelphia, PA: Wolters
Kluwer and Lippincott Williams &
Wilkins;2013:965-966.
[4] Warner, T. D.; Warner TD, Mitchell JA (2002).
"Cyclooxygenase-3 (COX-3): filling in the
gaps toward a COX continuum?" Proceedings
of the National Academy of Sciences of the
United States of America 99 (21): 133713.

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