Methyl salicylate

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Methyl salicylate

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
CAS number	[119-36-8] [1]
SMILES	c1(O)ccccc1C(=O)OC
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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.

1 Botanical background
2 Commercial production
3 Uses
4 External links

[edit] Botanical background

Methyl salicylate may be toxic especially when taken internally, and plants containing methyl salicylate may have evolved it 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 (PMID 15537163). 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 a odor masking agent for some organophosphate pesticides. If applied in too high quantities it can cause stomach and kidney problems.

It also has the property of fluorescence, converting ultraviolet light into visible blue light.

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.