Methyl salicylate

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Methyl salicylate
Skeletal formula
Ball-and-stick model
Space-filling model
Sample of a clear liquid
Names
IUPAC name
Methyl 2-hydroxybenzoate
Other names
Salicylic acid methyl ester; Oil of wintergreen; Betula oil; Methyl 2-hydroxybenzoate
Identifiers
119-36-8 YesY
ChEMBL ChEMBL108545 YesY
ChemSpider 13848808 YesY
2431
Jmol 3D model Interactive image
KEGG D01087 YesY
UNII LAV5U5022Y YesY
  • InChI=1S/C8H8O3/c1-11-8(10)6-4-2-3-5-7(6)9/h2-5,9H,1H3 YesY
    Key: OSWPMRLSEDHDFF-UHFFFAOYSA-N YesY
  • InChI=1/C8H8O3/c1-11-8(10)6-4-2-3-5-7(6)9/h2-5,9H,1H3
    Key: OSWPMRLSEDHDFF-UHFFFAOYAD
  • O=C(OC)c1ccccc1O
Properties
C8H8O3
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]
1.538
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY verify (what is YesYN ?)
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.[3]

Natural occurrence

File:Gaultheria procumbens.JPG
Wintergreen plants (Gaultheria procumbens)

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.[4] 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.[5]

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).

Uses

File:Chick embryo in methyl salicylate.jpg
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
  • in high concentrations as a rubefacient and analgesic in deep heating liniments (such as Bengay) to treat joint and muscular pain. Randomised double blind trial reviews report evidence of its effectiveness that is weak, but stronger for acute pain than chronic pain, and that effectiveness may be due entirely to counter-irritation. However, in the body it metabolizes into salicylates, including salicylic acid, a known NSAID.[6][7][8]
  • in low concentrations (0.04% and under)[9] as a flavoring agent in chewing gum and mints. When mixed with sugar and dried it is a potentially entertaining source of triboluminescence, gaining the tendency to build up electrical charge when crushed or rubbed. This effect can be observed by crushing wintergreen Life Savers in a dark room.[10][11]
  • providing fragrance to various products and as an odor-masking agent for some organophosphate pesticides.[citation needed]
  • as a bait for attracting male orchid bees for study, which apparently gather the chemical to synthesize pheromones.[12]
  • to clear plant or animal tissue samples of color, and as such is useful for microscopy and immunohistochemistry when excess pigments obscure structures or block light in the tissue being examined. This clearing generally only takes a few minutes, but the tissue must first be dehydrated in alcohol.[13]
  • as a transfer agent, to produce a manual copy of an image on a surface.[14]
  • in small amounts, to lower the freezing point of glacial acetic acid for transport.[citation needed]
  • a simulant or surrogate for the research of chemical warfare agent sulfur mustard, due to its similar chemical and physical properties.[15]
  • an antiseptic in Listerine mouthwash produced by the Johnson & Johnson company.[16]
  • restoring (at least temporarily) the elastomeric properties of old rubber rollers, especially in printers.[citation needed] [17]

Safety and toxicity

In pure form, methyl salicylate is toxic, especially when taken internally. A single teaspoon (5 ml) of methyl salicylate contains 7 g of salicylate,[18] 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,[19] (or 7.07 grams for a 70-kg adult). It has proven fatal to small children in doses as small as 4 ml.[9] 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.[20]

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.[21]

Compendial status

See also

References

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External links

  1. ↑ 1.0 1.1 Cite error: Invalid <ref> tag; no text was provided for refs named sigma
  2. ↑ 2.0 2.1 2.2 2.3 Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ See:
  4. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  6. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  7. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  8. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  9. ↑ 9.0 9.1 Wintergreen at Drugs.com
  10. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  11. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  12. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  13. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  14. ↑ Image Transfer at Making-greeting-cards.com
  15. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  16. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  17. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  18. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  19. ↑ Safety data for methyl salicylate, Physical & Theoretical Chemistry Laboratory, Oxford University
  20. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  21. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  22. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  23. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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