Methyl salicylate

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Methyl salicylate
Skeletal formula
Ball-and-stick modelSpace-filling model
Sample of a clear liquid
Identifiers
CAS number119-36-8 YesY
ChemSpider13848808 YesY
UNIILAV5U5022Y YesY
KEGGD01087 YesY
ChEMBLCHEMBL108545 YesY
Jmol-3D imagesImage 1
Properties
Molecular formulaC8H8O3
Molar mass152.1494 g/mol
Density1.174 g/cm³
Melting point−9 °C; 16 °F; 264 K
Boiling point220 - 224 °C
Hazards
Main hazardsHarmful
Flash point101 °C; 214 °F; 374 K
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references
 
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Methyl salicylate
Skeletal formula
Ball-and-stick modelSpace-filling model
Sample of a clear liquid
Identifiers
CAS number119-36-8 YesY
ChemSpider13848808 YesY
UNIILAV5U5022Y YesY
KEGGD01087 YesY
ChEMBLCHEMBL108545 YesY
Jmol-3D imagesImage 1
Properties
Molecular formulaC8H8O3
Molar mass152.1494 g/mol
Density1.174 g/cm³
Melting point−9 °C; 16 °F; 264 K
Boiling point220 - 224 °C
Hazards
Main hazardsHarmful
Flash point101 °C; 214 °F; 374 K
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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.[1]

Natural occurrence[edit]

Wintergreen plants (Gaultheria procumbens)

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

This compound is produced most likely 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.[2] 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.[3]

Commercial production[edit]

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).

Uses[edit]

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[edit]

In pure form, methyl salicylate is toxic, especially when taken internally. A single teaspoon (5ml) of methyl salicylate contains 7g of salicylate,[15] which is equivalent to more than twenty-three 300 mg aspirin tablets. The lowest published lethal dose is 101 mg/kg body weight in adult humans,[16] (or 7.07 grams for a 70-kg adult). It has proven fatal to small children in doses as small as 4 ml.[7] 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.[17]

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.[18]

Compendial status[edit]

See also[edit]

References[edit]

  1. ^ See:
  2. ^ 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. 
  3. ^ 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. 
  4. ^ "Topical analgesics introduction". Medicine.ox.ac.uk. 2003-05-26. Retrieved 2012-11-07. 
  5. ^ 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 404501. PMID 15033879. 
  6. ^ 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 404503. PMID 15105325. 
  7. ^ a b Wintergreen at Drugs.com
  8. ^ 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. 
  9. ^ "Why do Wint-O-Green Life Savers spark in the dark?". HowStuffWorks. 
  10. ^ "Sports cream overdose". Adam.about.com. 2009-09-30. Retrieved 2012-11-07. 
  11. ^ 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. 
  12. ^ Altman, J.S.; Tyrer, N.M. (1980). NJ Strausfeld, N.J.; Miller, T.A., ed. Neuroanatomical Techniques. Springer-Verlag. pp. 373–402. 
  13. ^ Image Transfer at Making-greeting-cards.com
  14. ^ 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. 
  15. ^ "Salicylate Poisoning - Patient UK". Patient.co.uk. 2011-04-20. Retrieved 2013-07-01. 
  16. ^ Safety data for methyl salicylate, Physical & Theoretical Chemistry Laboratory, Oxford University
  17. ^ "Muscle-Pain Reliever Is Blamed For Staten Island Runner’s Death". New York Times. 10 June 2007. 
  18. ^ 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. 
  19. ^ The British Pharmacopoeia Secretariat (2009). "Index, BP 2009". Retrieved 5 July 2009. 
  20. ^ "NIHS Japan". Moldb.nihs.go.jp. Retrieved 2013-07-01. 

External links[edit]