Everything about Methyl Salicylate totally explained
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Methyl salicylate (
chemical formula C
6H
4(HO)COOCH
3; 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
ester (a combination of an
organic acid with an
alcohol) most likely as an anti-
herbivore defense. If the plant is infested with herbivorous insects, the release of methyl salicylate may function as an aid in the recruitment of
beneficial insects to kill the herbivorous insects. 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. Numerous plants produce methyl salicylate in very small amounts.
Plants producing it in significant amounts (readily detected by scent) include:
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
Sweet Birch (
Betula lenta) and
Eastern Teaberry (
Gaultheria procumbens).
Uses
It is used as a
rubefacient in deep heating
liniments, and in small amounts as a
flavoring agent at no more than 0.04%. It is also used to provide
fragrance to various products and as an odor masking agent for some
organophosphate pesticides. If applied in too high quantities it can cause stomach and kidney problems.
It is one of many compounds that's attractive to males of various species of
orchid bees, who apparently gather the chemical to synthesize pheromones; it's commonly used as bait to attract and collect these bees for study.
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.
Methyl salicylate is used in some kinds of
chewing gum and
candy, as an alternative to the more common
peppermint and
spearmint oils. It is also a potentially entertaining source of
triboluminescence; when mixed with sugar and dried, it gains the tendency to build up electrical charge when ground. This effect can be observed by crushing wintergreen
Life Savers candy in a dark room.
Methyl salicylate can also be used as a transfer agent, to produce a manual copy of an image on a surface.
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. It has proven fatal to small children in doses as small as 4 mL. 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.
Further Information
Get more info on 'Methyl Salicylate'.
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