Experiment 7:

Synthesis of
Coumarin
GROUP 2
Almero, Leonardo Isaac
Dela Cruz, Jazmin
Gonzales, Omelyn
Racman, Ameerah
Vidallo, Yhiza Mae
What is Coumarin?

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 Coumarin

◉ IUPAC name: 2H-chromen-2-one

◉ Other name: 1-benzopyran-2-one
◉ Molecular formula: C9H6O2
◉ Molar mass: 146.15 g·mol−1
◉ Melting point: 71 °C (160 °F; 344 K)
◉ Boiling point: 301.71 °C (575.08 °F; 574.86 K)

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 Coumarin

◉ An organic compound that has

two six-membered rings fused
together, with one of the rings
being a benzene ring and the
other containing an alkene
functionality and an ester
functional group.

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 Coumarin

◉ Coumarins are colorless and crystalline

phytochemical substances.
◉ They belong to the family of benzopyrones, which
consists of benzene ring joined by a pyrone ring.

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 Background of Coumarin

◉ The name comes from a French

term for the tonka bean (Dipteryx
odorata), ”coumarou”, one of the
sources from which coumarin was
first isolated as a natural product in
1820.
◉ It has a sweet odor, readily
recognized as the scent of newly-
mown hay.
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 Uses of Coumarin

◉ They are used as enhancing agent in cosmetic products

like perfumes, soap, detergents, toothpaste and
alcoholic beverages.
◉ It is also used as a neutralizer in rubber and plastic
materials and also in paints and sprays to dilute the
unpleasant odors.

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 Uses of Coumarin

◉ Anticoagulant function
- They exhibit therapeutic effect by acting as
competitive inhibitors in the coagulation cascade
pathway. They inhibit the function of vitamin K which
is required for the biosynthesis of prothrombin.

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 Uses of Coumarin

◉ Treatment of Cancer
- Coumarins are very significant in the treatment of
cancer and is used in the treatment of prostate
cancer, renal cell carcinoma and leukemia.
- Coumarins have found to have good maintenance
therapy in case of melanoma and also found to
inhibit the spread of tumors.

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 Uses of Coumarin

◉ Edema
- Coumarins have potent edema protective function
and thus involved in the treatment of lymphedema,
elephantiasis and other high protein edema
conditions.
- Administration of coumarins along with vasoactive
drugs has a very high beneficial effect in the
treatment of edema.
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 Synthesis of Coumarin

◉ Pechmann Condensation

+ AlCl3

Phenol Ethyl acetoacetate

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Experiment 8:

Synthesis of
Aspirin
GROUP 2
Almero, Leonardo Isaac
Dela Cruz, Jazmin
Gonzales, Omelyn
Racman, Ameerah
Vidallo, Yhiza Mae
What is Aspirin?

13
 Aspirin

◉ IUPAC name: 2-Acetoxybenzoic acid

◉ Other name: Acetylsalicylic acid (ASA)
◉ Molecular formula: C9H8O4
◉ Molar mass: 180.158 g/mol
◉ Melting point: 136 °C (277 °F)
◉ Boiling point: 140 °C (284 °F)

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Aspirin

◉ Aspirin is both an organic

ester and an organic acid.
◉ It is used extensively as a
pain killer (analgesic) and
as a fever-reducing drug
(antipyretic).

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History of Aspirin

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 Uses of Aspirin

◉ Prescription aspirin is used to relieve the symptoms of:

- Rheumatoid arthritis
- Osteoarthritis
- Systemic lupus erythematosus

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 Uses of Aspirin

◉ Nonprescription aspirin is used to:

- reduce fever
- relieve mild to moderate pain from headaches,
menstrual periods, arthritis, colds, toothaches, and
muscle aches
- prevent heart attacks
- prevent ischemic stroke
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 Synthesis of Aspirin

H2SO4

Acetic acid
Salicylic acid Acetic anhydride Acetylsalicylic Acid

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 Preparation of Aspirin

◉ The synthesis of Aspirin, during the first step of the

procedure, is classified as an esterification procedure.
◉ Esterification is a reaction between a carboxylic acid
and an alcohol which is catalyzed by a mineral acid
which is, in our experiment, sulfuric acid.

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 Preparation of Aspirin

1. Place 2 g of Salicylic acid in a 250 mL erlenmeyer flask

2. In the fume hood, add 5 mL of acetic anhydride into the
flask using a buret, and add 5 drops of conc. sulfuric
acid (catalyst) to the mixture.
3. Gently heat in a boiling water bath for 10 minutes.
4. Slowly add 10 mL of distilled water to decompose any
excess acetic anhydride.

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 Preparation of Aspirin

5. Let the flask cool to room temperature, and as the

solution cools, crystals of aspirin will appear.
6. Set up a vacuum filtration apparatus.
7. Wash the crystal produced with 5-10 mL of cold distilled
water.
8. Maintain the vacuum to dry the crystals as best
possible.
9. Determine the mass of the crude aspirin crystals.
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 Recrystallization of
Aspirin

1. Place the aspirin crystals in a 100 mL beaker and add 8

mL of ethanol and 25 mL of distilled water
2. Warm the mixt. in a 60 °C water bath, until the aspirin
dissolves.
3. Cover the beaker with watch glass and set it aside to
cool slowly.
4. Place the beaker in an ice bath until needle-like crystals
of acetylsalicylic acid is formed
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 Recrystallization of
Aspirin

5. Collect the aspirin crystals by vacuum filtration and

wash with 10 mL cold distilled water.
6. Maintain the vacuum to air dry the aspirin.
7. Transfer the dry aspirin to a container/vial.
8. Determine the mass of the aspirin crystal.

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 Melting point
determination of Aspirin

1. Fill the capillary melting point tube to a depth of 0.2 cm

with the recrystallized aspirin
2. Place the capillary tube in a melting point apparatus.
Determine its melting point.

◉ Pure aspirin melts at 135 °C

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Thanks!
Prepared by:
GROUP #2 – PH2-01
Almero, Leonardo Isaac
Dela Cruz, Jazmin
Gonzales, Omelyn
Racman, Ameerah
Vidallo, Yhiza Mae

Laboratory Teacher:
Mr. Roland Amiel Peñaloza
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References: COUMARIN
◉ https://en.wikipedia.org/wiki/Coumarin

◉ Bruneton J (1999) Pharmacognosy, Phytochemistry, Medicinal Plants

Second Edition, Hampshire UK, Intercept, pp. 263-277.

◉ Ojala T (2001) Biological Screening of Plant Coumarins. PhD Thesis,

University of Helsinki, Helsinki, Finland.

◉ Lacy A, O'Kennedy R (2004) Studies on coumarins and coumarin-related

compounds to determine their therapeutic role in the treatment of
cancer. Curr Pharm Des 10: 3797-3811.

◉ Cohen SM, Ellwein LB (1991) Genetic errors, cell proliferation, and

carcinogenesis. Cancer Res 51: 6493-6505.
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References: COUMARIN
◉ Fentem JH, Fry JR (1993) Species differences in the metabolism and
hepatotoxicity of coumarin. CompBiochemPhysiol C 104: 1-8.

◉ Goodman & Gilman’s (2006) The Pharmacological basis of therapeutics:

Blood coagulation and Anti-coagulant, thrombolytic and Anti-platelet
drugs, pp. 1325-1328.

◉ Finn GJ, Kenealy E, Creaven BS, Egan DA (2002) In vitro cytotoxic

potential and mechanism of action of selected coumarins, using human
renal cell lines. Cancer Lett 183: 61-68.

◉ Loprinzi CL, Kugler JW, Sloan JA, Rooke TW, Quella SK, et al. (1999) Lack
of effect of coumarin in women with lymphedema after treatment for
breast cancer. N Engl J Med 340: 346-350. 28
References: COUMARIN
◉ Freemantle M (2016) The Royal Society of Chemistry: Coumarin.
https://www.chemistryworld.com/podcasts/coumarin/1010225.article.

◉ Casley-Smith JR, Casley-Smith JR (1997) Coumarin in the Treatment of

Lymphoedema and Other High-Protein Oedemas. Coumarins: Biology, Applications
and Mode of Action. Chichester, John Wiley & Sons, pp. 143-184.

◉ Casley-Smith JR, Jamal S, Casley-Smith J (1993) Reduction of filariticlymphoedema

and elephantiasis by 5,6 benzo-alpha-pyrone (coumarin), and the effects of
diethylcarbamazine (DEC). Ann Trop Med Parasitol 87: 247-258.

◉ Casley-Smith JR, Morgan RG, Piller NB (1993) Treatment of lymphedema of the arms
and legs with 5,6-benzo-[alpha]-pyrone. N Engl J Med 329: 1158-1163.

◉ Rohini K, Srikumar PS (2014) Therapeutic Role of Coumarins and Coumarin-Related

Compounds. J Thermodyn Catal 5:130. Doi: 10.4172/2157-7544.1000130.
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References: ASPIRIN
◉ US National Library of Medicine. MedLine Plus.
https://medlineplus.gov/druginfo/meds/a682878.html

◉ https://en.wikipedia.org/wiki/Aspirin

◉ TED-Ed. “How Aspirin was discovered”.

https://www.youtube.com/watch?v=uRhkDN2WjzI

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