Methyl Salicylate

Final Project

Chemistry

1106

From:

Alinnan Thiptanakit (5861001)

To:

Miss Patraphorn Sanguansat

 Introduction:

- Methyl Salicylate is an organic ester naturally produced by many species of plants, particularly

wintergreens. It is also synthetically produced, used as a fragrance, in foods and beverages,

and in liniments. The compound methyl salicylate was first discovered in 1843 by the French

chemist Auguste Andr Thomas Cahours (18131891), who identified it as an ester of salicylic

acid and methanol. Methyl Salicylate is also known as Methyl 2-hydroxybenzoate (IUPAC),

Salicylic acid methyl ester; Oil of wintergreen; Betula oil; Methyl 2-hydroxybenzoate. It can

either be synthesized or extracted from the leaves of Gaultheria procumbens (Ericaceae) and

bark of Betula lenta (Betulaceae) Sweetman (2003). [ 6]

Chemical Properties:
Property Name Property Value

Molecular Weight 152.149 g/mol

Hydrogen Bond Donor Count 1

Hydrogen Bond Acceptor Count 3

Rotatable Bond Count 2

Complexity 144

CACTVS Substructure Key Fingerprint AAADccBwMAAAAAAAAAAAAAAAAA

AAAAAAAAAwAAAAAAAAAAABAAAA
GgAACAAADASAmAIyDoAABgCIAiDSC
AACAAAkIAAIiAEGCMgIJzaCNRqAcUAl
4BEIuYeIyCCOAAAAAAAIAAAAAAAAA
BAAAAAAAAAA

Topological Polar Surface Area 46.5 A^2

Monoisotopic Mass 152.047 g/mol

 Exact Mass 152.047 g/mol

XLogP3 2.3

Compound Is Canonicalized true

Formal Charge 0

Heavy Atom Count 11

Defined Atom Stereocenter Count 0

Undefined Atom Stereocenter Count 0

Defined Bond Stereocenter Count 0

Undefined Bond Stereocenter Count 0

Isotope Atom Count 0

Covalently-Bonded Unit Count 1

Physical Property
1. Physical Description

Methyl salicylate is a colorless yellowish or reddish liquid with odor of wintergreen. [ 8]

 Liquid. [ 7 ]
Colorless or yellow to red oily liquid with characteristic odor. [ 3]
2. Color

Colorless, yellowish or reddish, oily liquid. [ 1]

3. Odor

Liquid having the characteristics odor of wintergreen. [ 2]

4. Taste

Liquid having the characteristics taste of wintergreen. [ 2]

5. Boiling Point

432 F at 760 mm Hg [ 7]
220-224 DEG C [ 1 ]
222C [ 3 ]

6. Melting Point

16.5 F [ 7 ]
(-8.6 DEG C). [ 1]
(-8.6 C). [ 3 ]

7. Solubility

less than 1 mg/mL at 66 F [ 7 ]

Solution in diethyl ether. [ 7 ]
Soluble in most common organic solvents. [ 7]
Sol in water: 0.74%w @ 30 deg C. [ 7 ]
0.7 mg/mL at 30 C [ 3 ]
in water, g/100ml at 20C: 0.07 [ 3 ]

8. Density

1.174 [ 7 ]
1.184 @ 25 DEG C/25 DEG C. [ 1]
(water = 1): 1.18. [ 3 ]

9. Vapor Density

5.24 (Relative to Air) [ 7]

5.2 [ 7 ]
(air = 1): 5.24. [ 3 ]
 10. Vapor Pressure

0.0975 mm Hg at 68 F ; 1 mm Hg at 129 F [ 7 ]
Vapor pressure = 0.0343 mm Hg @ 25 deg C. [ 7 ]
Vapour pressure: Pa at 20C: 6. [ 3 ]

Applications
Methyl Salicylate is used for temporary relief of minor aches and pains caused by

arthritis, simple backache, strains, sprains, and bruises. And Methyl Salicylate can also be used

to make medicines or ointment. [ 5]

References
1. Budavari, S. (ed.). The Merck Index - Encyclopedia of Chemicals, Drugs and Biologicals.

Rahway, NJ: Merck and Co., Inc., 1989., p. 961

2. Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New

York: Macmillan Publishing Co., Inc., 1975., p. 335

3. ILO-ICSC. (2004, October 28). Methyl Salicylate. Retrieved May 17, 2017, from

http://www.ilo.org/dyn/icsc/showcard.display?p_card_id=1505
4. Index, M. (1976). Methyl Salicylate. Retrieved May 23, 2017, from http://ac.els-

cdn.com/S0015626478801321/1-s2.0-S0015626478801321-main.pdf?_tid=1901fe8e-3f67-

11e7-9e07-00000aab0f6c&acdnat=1495509949_2ba601746ca5547dcb25d38387cb3185
5. Methyl-salicylate-menthol-ointment : Uses, Side Effects, Interactions, Pictures, Warnings &

Dosing. (2005). Retrieved May 17, 2017, from http://www.webmd.com/drugs/2/drug-18536-

8226/methyl-salicylate-menthol-ointment/details
6. Miles, S. (2007). Salicylic acid. Retrieved May 17, 2017, from

http://www.sciencedirect.com/topics/page/Salicylic_acid
7. NOAA Office of Response and Restoration, US GOV. (n.d.). Search Chemicals.
8. Retrieved May 17, 2017, from https://cameochemicals.noaa.gov/chemical/17825
9. Pubchem. (2005, March 25). Methyl salicylate. Retrieved May 17, 2017, from

https://pubchem.ncbi.nlm.nih.gov/compound/methyl_salicylate#section=Flash-Point