Methyl salicylate



Methyl salicylate
IUPAC name Methyl salicylate
Identifiers
CAS number 119-36-8
SMILES c1(O)ccccc1C(=O)OC
Properties
Molecular formula C8H8O3
Molar mass 152.1494 g/mol
Density 1.174 g/cm³
Melting point

-9 °C

Boiling point

220 - 224 °C

Hazards
Flash point 101 °C
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references

Methyl salicylate (chemical formula C6H4(HO)COOCH3; also known as salicylic acid methyl ester, oil of wintergreen, betula oil, methyl-2-hydroxybenzoate) is a natural product of many species of plants. Some of the plants producing it are called wintergreens, hence the common name.

Botanical background

Plants containing methyl salicylate produce this organic pathogens such as tobacco mosaic virus.[2] Numerous plants produce methyl salicylate in very small amounts.

Plants producing it in significant amounts (readily detected by scent) include:

  • Most species of the family Pyrolaceae, particularly those in the genus Pyrola.
  • Some species of the genus Gaultheria in the family Ericaceae.
  • Some species of the genus Betula in the family Betulaceae, particularly those in the subgenus Betulenta.

Commercial production

Methyl salicylate can be produced by Eastern Teaberry (Gaultheria procumbens).

Uses

It is used as a organophosphate pesticides. If applied in too high quantities it can cause stomach and kidney problems.[citation needed]

It is one of many compounds that is attractive to males of various species of orchid bees, who apparently gather the chemical to synthesize pheromones; it is commonly used as bait to attract and collect these bees for study.[4]

Methyl salicylate also has the ability 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.[citation needed]

Methyl salicylate can also be used as a transfer agent, to produce a manual copy of an image on a surface.[5]

Safety

In pure form, methyl salicylate is toxic, especially when taken internally. The lowest published lethal dose is 101 mg/kg body weight in adult humans.[6] It has proven fatal to small children in doses as small as 4 mL.[7] A 17 year-old cross-country runner at Notre Dame Academy on Staten Island, died April 3, 2007, after her body absorbed high levels of methyl salicylate through excessive use of topical muscle-pain relief products.[8]

See also

References

  1. ^ D. G. James, T. S. Price (Aug 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.
  2. ^ Vladimir Shulaev, Paul Silverman, Ilya Raskin (20 Feb 1997). "Airborne signalling by methyl salicylate in plant pathogen resistance". Nature 385: 718 - 721. doi:10.1038/385718a0.
  3. ^ Wintergreen at Drugs.com
  4. ^ Schiestl, F.P.; Roubik, D.W. (2004). "Odor Compound Detection in Male Euglossine Bees.". Journal of Chemical Ecology 29: 253-257. doi:10.1023/A:1021932131526.
  5. ^ Image Transfer at Making-greeting-cards.com
  6. ^ Safety data for methyl salicylate, Physical & Theoretical Chemistry Laboratory, Oxford University
  7. ^ Wintergreen at Drugs.com
  8. ^ "Muscle-Pain Reliever Is Blamed For Staten Island Runner’s Death", New York Times, 2007-06-10. Retrieved on 2007-06-09. 
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Methyl_salicylate". A list of authors is available in Wikipedia.