Methyl Salicylate

Description

Methyl salicylate (oil of wintergreen or wintergreen oil) is an organic compound with the formula C₈H₈O₃. It is the methyl ester of salicylic acid. It is a colorless, viscous liquid with a sweet, fruity odor reminiscent of root beer (in which it is used as a flavoring), but often associatively called “minty”, as it is an ingredient in mint candies. It is produced by many species of plants, particularly wintergreens. Methyl Salicylate is also produced synthetically, used as a fragrance and as a flavoring agent.

 

Methyl Salicylate Biosynthesis And Occurrence

Methyl salicylate was first isolated (from the plant Gaultheria procumbens) in 1843 by the French chemist Auguste André Thomas Cahours (1813–1891), who identified it as an ester of salicylic acid and methanol.

The biosynthesis of methyl salicylate arises via the hydroxylation of benzoic acid by a cytochrome P450 followed by methylation by a methylase enzyme.

 

Methyl Salicylate As a Plant Metabolite

 

Many plants produce methyl salicylate in small quantities. Methyl salicylate levels are often upregulated in response to biotic stress, especially infection by pathogens, where it plays a role in the induction of resistance.

Methyl salicylate is believed to function by being metabolized to the plant hormone salicylic acid. Since methyl salicylate is volatile, these signals can spread through the air to distal parts of the same plant or even to neighboring plants, whereupon they can function as a mechanism of plant-to-plant communication, “warning” neighbors of danger.

Methyl salicylate is also released in some plants when they are damaged by herbivorous insects, where they may function as a cue aiding in the recruitment of predators.

 

Methyl Salicylate Specifications