Methyl salicylate
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| Methyl salicylate | |
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| Chemical name | Methyl salicylate |
| Chemical formula | C8H8O3 |
| Molecular mass | 152.1494 g/mol |
| CAS number | [119-36-8] |
| Density | 1.174 g/cm3 |
| Melting point | -9 °C |
| Boiling point | 220 - 224 °C |
| Flash Point | 101 °C |
| CAS number | [119-36-8] [1] |
| SMILES | c1(O)ccccc1C(=O)OC |
| 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.
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[edit] Botanical background
In pure form, even in small amounts, this ester is toxic--especially when taken internally. It has proven fatal to small childen in doses as small as a single teaspoon. Plants containing methyl salicylate produce this organic ester (a combination of an organic acid with an alchohol) most likely as an anti-herbivore defence. Aside from its toxicity, methyl salicylate may be used by plants as a pheromone to warn other plants of pathogens such as tobacco mosaic virus [2]. If the plant is infested with herbivorous insects, the release of methyl salicylate may function as an exopheromone aid in the recruitment of beneficial insects to kill the herbivorous insects.[1] 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.
[edit] Commercial production
Structurally, it is the methyl ester of salicylic acid. Hence, it can be produced from the condensation reaction of salicylic acid and methanol. Commercial methyl salicylate is now synthesized, but in the past, it was commonly distilled from the twigs of Sweet Birch (Betula lenta) and Eastern Teaberry (Gaultheria procumbens).
[edit] Uses
It is used as a rubefacient in deep heating liniments, and in small amounts as a flavoring agent. It is also used to provide fragrance to various products. It is also used as an odor masking agent for some organophosphate pesticides. If applied in too high quantities it can cause stomach and kidney problems.
Methyl salicylate also has the ability to clear plant or animal tissue samples of colour, 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.
[edit] References
- ^ James DG, Price TS. "Field-testing of methyl salicylate for recruitment and retention of beneficial insects in grapes and hops." J Chem Ecol. 2004 Aug;30(8):1613-28. PMID 15537163
[edit] External links
- Toxicity
