The chemical compound methyl salicylate, often known as wintergreen oil or wintergreen oil, has the formula C8H8O3. It is salicylic acid's methyl ester. It is a clear, viscous liquid that is commonly referred to as "minty" since it is a component of mint candies. It has a sweet, fruity aroma reminiscent of root beer. Numerous plant species, especially wintergreens, generate it. Additionally, it is made synthetically and serves as a flavoring and fragrance ingredient.
The French scientist Auguste André Thomas Cahours (1813–1891), who first isolated methyl salicylate in 1843 (from the plant Gaultheria procumbens), recognized it as an ester of salicylic acid and methanol.The hydroxylation of benzoic acid by a cytochrome P450 enzyme and subsequent methylation by a methylase enzyme result in the production of methyl salicylate.Salicylic acid and methanol can be esterified to create methyl salicylate.However, in the past, it was frequently distilled from the twigs of Betula lenta (sweet birch) and Gaultheria procumbens (eastern teaberry or wintergreen). Nowadays, commercial methyl salicylate is manufactured.
In deep heating liniments used to treat joint and muscle pain, methyl salicylate is utilized in high doses as a rubefacient and analgesic. Randomized double-blind studies found mixed evidence for its efficacy, with evidence for acute pain being stronger than for chronic pain. The benefit may be completely attributable to counterirritation.However, in the body it metabolizes into salicylates, including salicylic acid, a known NSAID.
Methyl salicylate is used in low concentrations (0.04% and under) as a flavoring agent in chewing gum and mints. It is a potentially interesting source of triboluminescence when combined with sugar and dried. The light that is released when sugar crystals are broken is amplified by methyl salicylate because it fluoresces, absorbing ultraviolet light and reemitting it in the visible band. It serves as an odor-masking ingredient for several organophosphate insecticides and adds scent to a variety of items.Due to its similar chemical and physical properties, sulfur mustard is also used as a surrogate for research on the chemical warfare agent sulfur mustard, as a transfer agent in printmaking (to release toner from photocopied images and apply them to other surfaces), as a penetrating oil to loosen rusted components, and in restoring (at least temporarily) the elastomeric properties of old rubber rollers, particularly in printers.
Methyl salicylate may be fatal, especially to small infants, who can unintentionally consume anything containing it, such as an essential oil solution. Six grams of salicylate, or around twenty 300 mg aspirin pills, are present in one teaspoon (5 mL) of methyl salicylate.
Salicylate poisoning usually results from levels of around 150 mg/kg body weight. This may be accomplished using 1 mL of oil of wintergreen or 140 mg/kg of salicylates for a kid weighing 10 kg (22 lbs). For adult humans, the lowest documented fatal dosage is 101 mg/kg body weight. In dosages as small as 4 mL, it has been shown to be lethal to young children.The majority of cases of methyl salicylate poisoning in humans, particularly in children, are brought on by excessive use of topical analgesics. The main metabolite of methyl salicylate, salicylate, can build up in blood, plasma, or serum, which can be used to confirm poisoning in hospitalized patients or facilitate autopsies.
