Methyl salicylate

Methyl salicylate
Skeletal formula
Ball-and-stick model
Space-filling model
Sample of a clear liquid
IUPAC name
Methyl 2-hydroxybenzoate
Other names
Salicylic acid methyl ester; Oil of wintergreen; Betula oil; Methyl 2-hydroxybenzoate
119-36-8 YesY
3D model (Jmol) Interactive image
ChEMBL ChEMBL108545 YesY
ChemSpider 13848808 YesY
ECHA InfoCard 100.003.925
KEGG D01087 YesY
Molar mass 152.15 g·mol−1
Density 1.174 g/cm3
Melting point −8.6 °C (16.5 °F; 264.5 K)
Boiling point 222 °C (432 °F; 495 K) [1]
decomposes at 340-350 °C[2]
0.639 g/L (21 °C)
0.697 g/L (30°C)[2]
Solubility miscible in diethyl ether, ethanol[2]
Solubility in acetone 10.1 g/g (30 °C)[2]
Vapor pressure 1 mmHg (54 °C)[1]
Acidity (pKa) 9.8[3]
Main hazards Harmful
GHS pictograms [1]
GHS signal word Warning
R-phrases R22
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 96 °C (205 °F; 369 K) [1]
452.7 °C (846.9 °F; 725.8 K) [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Methyl salicylate (oil of wintergreen or wintergreen oil) 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 isolated (from the plant Gaultheria procumbens) in 1843 by the French chemist Auguste André Thomas Cahours (1813–1891), who identified it as an ester of salicylic acid and methanol.[4]

Natural occurrence

Wintergreen plants (Gaultheria procumbens)

This compound is probably produced as an anti-herbivore defense. If the plant is infected with herbivorous insects, the release of methyl salicylate may function as an aid in the recruitment of beneficial insects to kill the herbivorous insects.[5] Aside from its toxicity, methyl salicylate may also be used by plants as a pheromone to warn other plants of pathogens such as tobacco mosaic virus.[6]

Numerous plants produce methyl salicylate in very small amounts. Some plants, such as the following, produce more:

Commercial production

Methyl salicylate can be produced by esterifying salicylic acid with methanol. Commercial methyl salicylate is now synthesized, but in the past, it was commonly distilled from the twigs of Betula lenta (sweet birch) and Gaultheria procumbens (eastern teaberry or wintergreen).


Chick embryo that was treated with methylene blue to stain the skeleton, then cleansed with 2 or 3 ethanol washes, and treated with methyl salicylate to make the surrounding tissues transparent

Safety and toxicity

In pure form, methyl salicylate is harmful, when taken orally. A single teaspoon (5 ml) of methyl salicylate contains approximately 6 g of salicylate,[19] which is equivalent to almost twenty 300 mg aspirin tablets (5 mL * 1.174 g/mL = 5.87 g). The lowest published lethal dose is 101 mg/kg body weight in adult humans,[20] (or 7.07 grams for a 70-kg adult). It has proven fatal to small children in doses as small as 4 ml.[10] A seventeen-year-old cross-country runner at Notre Dame Academy on Staten Island died in April 2007 after her body absorbed methyl salicylate through excessive use of topical muscle-pain relief products.[21]

Most instances of human toxicity due to methyl salicylate are a result of over-application of topical analgesics, especially involving children. Some people have intentionally ingested large amounts of oil of wintergreen. Salicylate, the major metabolite of methyl salicylate, may be quantitated in blood, plasma or serum to confirm a diagnosis of poisoning in hospitalized patients or to assist in an autopsy.[22]

Compendial status

See also


  1. 1 2 3 4 5 6 Sigma-Aldrich Co., Methyl salicylate. Retrieved on 2013-05-23.
  2. 1 2 3 4 "methyl salicylate".
  3. Scully, Frank E.; Hoigné, Jürg (January 1987). "Rate constants for reactions of singlet oxygen with phenols and other compounds in water". Chemosphere. 16 (4): 681–694. doi:10.1016/0045-6535(87)90004-X.
  4. See:
  5. D. G. James; T. S. Price (August 2004). "Field-testing of methyl salicylate for recruitment and retention of beneficial insects in grapes and hops". J. Chem. Ecol. 30 (8): 1613–28. doi:10.1023/B:JOEC.0000042072.18151.6f. PMID 15537163.
  6. Vladimir Shulaev; Paul Silverman; Ilya Raskin (20 February 1997). "Airborne signalling by methyl salicylate in plant pathogen resistance". Nature. 385 (6618): 718–721. Bibcode:1997Natur.385..718S. doi:10.1038/385718a0.
  7. "Topical analgesics introduction". 2003-05-26. Retrieved 2012-11-07.
  8. Mason, L.; Moore, RA; Edwards, JE; McQuay, HJ; Derry, S; Wiffen, PJ (2004). "Systematic review of efficacy of topical rubefacients containing salicylates for the treatment of acute and chronic pain". BMJ. 328 (7446): 995. doi:10.1136/bmj.38040.607141.EE. PMC 404501Freely accessible. PMID 15033879.
  9. Tramer, M. R (2004). "It's not just about rubbing--topical capsaicin and topical salicylates may be useful as adjuvants to conventional pain treatment". BMJ. 328 (7446): 998. doi:10.1136/bmj.328.7446.998. PMC 404503Freely accessible. PMID 15105325.
  10. 1 2 Wintergreen at
  11. Harvey, E. N. (1939). "The luminescence of sugar wafers". Science. 90 (2324): 35–36. Bibcode:1939Sci....90...35N. doi:10.1126/science.90.2324.35. PMID 17798129.
  12. "Why do Wint-O-Green Life Savers spark in the dark?". HowStuffWorks.
  13. Schiestl, F.P.; Roubik, D.W. (2004). "Odor Compound Detection in Male Euglossine Bees". Journal of Chemical Ecology. 29 (1): 253–257. doi:10.1023/A:1021932131526. PMID 12647866.
  14. Altman, J.S.; Tyrer, N.M. (1980). "Filling selected neurons with cobalt through cut axons". In NJ Strausfeld, N.J.; Miller, T.A. Neuroanatomical Techniques. Springer-Verlag. pp. 373–402. Missing or empty |title= (help)
  15. Image Transfer at
  16. Bartlet-Hunt, S. L.; Knappe, Detlef R. U.; et al. (2008). "A Review of Chemical Warfare Agent Simulants for the Study of Environmental Behaviour". Critical Reviews in Environmental Science and Technology. 38 (2): 112–136. doi:10.1080/10643380701643650.
  17. Listerine. "Original Listerine Antiseptic Mouthwash". Retrieved 25 March 2015.
  18. "MG Chemicals - Rubber Renue Safety Data Sheet" (PDF).
  19. "Salicylate Poisoning - Patient UK". 2011-04-20. Retrieved 2013-07-01.
  20. Safety data for methyl salicylate, Physical & Theoretical Chemistry Laboratory, Oxford University
  21. "Muscle-Pain Reliever Is Blamed For Staten Island Runner's Death". New York Times. 10 June 2007.
  22. Baselt, R. (2008). Disposition of Toxic Drugs and Chemicals in Man (8th ed.). Foster City, CA: Biomedical Publications. pp. 1012–1014. ISBN 978-0-9626523-7-0.
  23. The British Pharmacopoeia Secretariat (2009). "Index, BP 2009" (PDF). Archived from the original (PDF) on 11 April 2009. Retrieved 5 July 2009.
  24. "NIHS Japan". Retrieved 2013-07-01.
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