Eugenol

A phenylpropene, an allyl chain-substituted guaiacol

Eugenol

Eugenol biosynthesis pathway

Eugenol is a phenylpropene, a type of phenylpropanoid compound, and is a member of the allylbenzene class of chemical compounds. It is a colorless to pale yellow, aromatic oily liquid extracted from certain essential oils especially from clove oil, nutmeg, cinnamon, basil, and bay leaf. It is used in perfumes, flavorings, and in medicine as a local antiseptic and anesthetic.

Chemical properties

Eugenol has the chemical formula C__H__O_. It is an allyl chain-substituted guaiacol. Eugenol is slightly soluble in water and soluble in organic solvents. It has a boiling point of 254 °C and a density of 1.06 g/cm_.

Biosynthesis

Eugenol is biosynthesized from the amino acid phenylalanine via the shikimate pathway. The biosynthesis involves the conversion of phenylalanine to cinnamic acid, which is then converted to p-coumaric acid, followed by the formation of caffeic acid. Caffeic acid is then converted to ferulic acid, which is the direct precursor of eugenol. The enzyme eugenol synthase catalyzes the final step in the biosynthesis of eugenol from ferulic acid.

Uses

Eugenol is widely used in the perfume and flavoring industries due to its pleasant aroma. In the medical field, it is used as a local antiseptic and anesthetic. Eugenol is also used in dentistry for its analgesic and antiseptic properties, often in the form of zinc oxide eugenol cement.

Safety

Eugenol is generally recognized as safe when used in small amounts as a flavoring agent. However, it can be toxic in large doses and may cause allergic reactions in some individuals. It is important to handle eugenol with care, as it can cause irritation to the skin and eyes.

Related pages

• Phenylpropene
• Essential oil
• Clove oil
• Shikimate pathway