Methyl Salicylate - C8H8O3

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

Methyl Salicylate Structure – C8H8O3

Physical Properties of Methyl Salicylate – C8H8O3

Odour Minty cool
Appearance Colourless to yellow or reddish liquid
Vapour 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 an 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.

Frequently Asked Questions

What is methyl salicylate used for?

Topical methyl salicylate (for the skin) is used for acute muscle relaxation or joint pain caused by strains, sprains, inflammation, swelling, or backaches. Methyl salicylate topical can also be used for uses that are not specified in this drug guide.

How does methyl salicylate relieve pain?

The counterirritants are called menthol and methyl salicylate. They work by making the skin feel cool and dry, afterwards. Such skin sensations prevent you from experiencing deeper the aches / pains in your muscles, joints and tendons.

What is the chemical difference between salicylic acid and methyl salicylate?

The COOH group of salicylic acid is esterified with methanol (CH3OH) in methyl salicylate (winter green oil), while the acid portion of the ester in acetylsalicylic acid (aspirin) is acetic acid, and salicylic acid contributes to the phenolic −OH community.

Where does methyl salicylate come from?

This is a derivative of salicylic acid. Methyl salicylate (winter-green or winter-green oil) is an organic ester produced naturally by many plant species, particularly winter-greens. In 1843, the compound was first extracted and isolated from Gaultheria procumbens plant material.

Is methyl salicylate more polar than salicylic acid?

The distinction between the two is that aspirin is salicylic acid which has been esterified with the free OH of salicylic acid. Both compounds appear to have the group -COOH. So, this is about matching -OH to -OC = OCH3. The group -OH is more polar than the ester and thus salicylic acid is more polar than aspirin.

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