I. Garcia, Mary Antoinette B.

Janio, John Albert T.

Javier, Phoebe Isabel V.
Jimenez, Joshua M.

II. Date Performed: 18 January 2017

III. Date Submission:
IV. Discussion of Theory
Salicylates were one of the first group of compounds to receive recognition as
analgesics. In 1829, Henri Leroux, a French pharmacist, improved the
purification process initially conceived by Johann Buchner, and obtained
salicin in its crystalline form for the first time. Salicylates promote the
excretion of uric acid, and therefore found use in the treatment of gouty
arthritis. Salicylates in general, are known to exert their antipyretic action in
febrile patients, by increasing heat elimination of the body via the mobilization
of water and consequent dilution of the blood.

Methyl Salicylate, C6H4 (HO) COOCH3 also known as salicylic acid methyl
ester, Gaultheria oil, or Oil of Wintergreen, is a natural product of many plant
species. It has been used
V. Chemical Reaction:

OH

OH H 2S O O
4

+ H3C OH
+ H OH
O O
CH3
OH
2-hydroxybenzoic acid methanol methyl 2-hydroxybenzoate water

VI. Questions for Research

1. Enumerate the physicochemical properties of methyl salicylate

Physico Chemical Property

Molecular Weight 152.149g/mol
 Colorless to yellow to red oily liquid,
Physical description
with characteristic odor
Taste Liquid, having the taste of Wintergreen
Boiling point 220 224 C
Melting point -8.6 C
Soluble in chloroform, ether; Miscible in
Solubility
alcohol, glacial acetic acid.
Density 1.184 at 25C
Surface Tension 44.2 dynes/cm
Index of Refraction 1.5369 at 20C
Source: National Center for Biotechnology Information. (2005, March 25).
Methyl Salicylate. Retrieved from PubChem Open Chemistry Database:
https://pubchem.ncbi.nlm.nih.gov/compound/methyl_salicylate#section=Top
2. What are the other methods of obtaining methyl salicylate?

Wintergreen oil is water steam distilled from the leaves charged into the
still and allowed to macerate for several hours, in order to hydrolyze
gaultherin glucoside (Methyl salicylate + glucose). Distillation from 5 6
hours yield approximately 0.7% essential oil (Furia & Bellanca, 1975).

However, the compound is mostly prepared through the esterification of

salicylic acid with methanol, which is about 99% pure commercially
prepared methyl salicylate. (Merck and Co., Inc., 1989)

3. What are the other names given to methyl salicylate?

Methyl salicylate is known in various synonyms: Methyl 2

hydroxybenzoate, Gaultheria oil, Wintergreen oil, Betula oil, Sweet birch
oil, or Spicewood oil.

4. Describe the use of methyl salicylate in local applications and give five
preparations which contain the drug and include the use and
manufacturers.

Begesic Cream (Cajuput oil, Eugenol, Menthol, Methyl Salicylate) Littman

Kamillosan M Spray (Anise oil, Bergamot oil, Chamomile extr, Cineol,
Methyl salicylate, peppermint oil, dwarf pine needle oil, sage oil) A.
Menarini [Zuellig]
Listerine Mouthwash (Alcohol, benzoic acid, eucalyptol, methyl salicylate,
Thymol, methanol) Johnson & Johnson
Salonpas Pain Patch

5. Give out toxic effects that can be experienced from methyl salicylate

VII. References
Furia, T., & Bellanca, N. (1975). Fenaroli's Handbook of Flavor Ingredients (Vol. 1).
Cleveland: The Chemical Rubber Co.

La Gatta, F. (2007, August 1). Synthesis of Oil of Wintergreen. Retrieved from Cornell
Center for Materials Research: http://www.ccmr.cornell.edu/wp-
content/uploads/sites/2/2015/11/Synthesis-of-Oil-of-Wintergreen.pdf

Mahdi, J. G. (2010, July). Medicinal potential of willow: A chemical perspective of

aspirin discovery. Journal of Saudi Chemical Society, 14(3), 317 - 322.
doi:http://dx.doi.org/10.1016/j.jscs.2010.04.010

Merck and Co., Inc. (1989). The Merck Index - Encyclopedia of Chemicals, Drugs and
Biologicals.

National Center for Biotechnology Information. (2005, March 25). Methyl Salicylate.
Retrieved from PubChem Open Chemistry Database:
https://pubchem.ncbi.nlm.nih.gov/compound/methyl_salicylate#section=Top

Smith, P. K. (1960). The Pharmacology of Salicylates and Related Compounds.

Annals of the New York Academy of Sciences, 38 - 63. doi:10.1111/j.1749-
6632.1960.tb42789.x