Methyl Salicylate - C<sub>8</sub>H<sub>8</sub>O<sub>3</sub>

What is Methyl Salicylate?

Methyl salicylate sometimes called as wintergreen oil which is a sweet smelling member of the aspirin family is one of the most widely used as counterirritant. Methyl salicylate is the ester of salicylic acid in which the acidic carboxylate moiety is methylated but the phenolic hydroxyl is unchanged. Methyl salicylate is very similar in structure to salicylic acid. Salicylic acid is found in copious amounts in the bark of willow bark that could ease aches and reduce fever.

IUPAC name – Methyl 2-hydroxybenzoate

C6H4(OH)(CO2CH3)

Methyl Salicylate

Density

1.17 g/cm³

Molecular Weight/ Molar Mass

152.1494 g/mol

Melting Point

-9°C

Boiling Point

220°C

Compound Formula

C8H8O3

Methyl Salicylate Structure – C8H8O3

Methyl Salicylate

Physical Properties of Methyl Salicylate – C8H8O3

Odour

Minty cool

Appearance

Colorless to yellow or reddish liquid

Vapor Pressure

0.0343 mm Hg @ 25 deg C

Solubility

Slightly soluble in water and soluble in most organic solvents.

Chemical properties of Methyl Salicylate – C8H8O3

Methyl salicylate undergoes hydrolysis in the presence of aqueous base resulting in the formation of salicylic acid and methanol.

Formation of Salycilic Acid

Uses of Methyl Salicylate – C8H8O3

  • Very low concentration is used as a flavouring agent in candy, chewing gum, cough drops and toothpaste.
  • Used in aromatherapy as oil of wintergreen.
  • Used in cosmetics as a warming agent and in sport massage products as a rubefacient.
  • Used as a anti-inflammatory incorporated into liniments and ointments for joint and muscle pains.

Effects on Health

Methyl salicylate like other salicylates interferes with vitamin-k metabolism thereby decreasing blood clotting ability. For allergic individuals the risk of an adverse reaction is not dose related even a very small amount topically applied salicylate can generate an allergic response.

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