Eugenol

Molecular formula: C₁₀H₁₂O₂

Molecular weight: 164.20  
CAS No: 97-53-0
Solubility: slightly soluble in water and soluble in organic solvents

Density: 1.06 g/cm3
Melting point: −9 °C, 264 K, 16 °F
Boiling point 256 °C, 529 K, 493 °F

Eugenol is an allyl chain-substituted guaiacol. Eugenol is a member of the phenylpropanoids class of chemical compounds. It is a clear to pale yellow oily liquid extracted from certain essential oils especially from clove oil, nutmeg, cinnamon, basil and bay leaf. It is slightly soluble in water and soluble in organic solvents. It has a pleasant, spicy, clove-like aroma.

The name is derived from the scientific name for clove, Eugenia aromaticum or Eugenia caryophyllata. Eugenol is responsible for the aroma of cloves. It is the main component in the essential oil extracted from cloves, comprising 72-90% of the total.

Modern uses

Eugenol is used in perfumeries, flavorings, essential oils and in medicine as a local antiseptic and anesthetic. It is a key ingredient in Indonesian kretek (clove) cigarettes. It was used in the production of isoeugenol for the manufacture of vanillin, though most vanillin is now produced from phenol or from lignin.

When mixed with zinc oxide, eugenol forms a material which has restorative and prosthodontic applications in dentistry.

Eugenol derivatives or methoxyphenol derivatives in wider classification are used in perfumery and flavoring. They are used in formulating insect attractants and UV absorbers, analgesics, biocides, and antiseptics. They are also used in manufacturing stabilizers and antioxidants for plastics and rubbers. Although attempts have been made to develop eugenol derivatives for intravenous injection, such as propanidid and G.29.505, there were unacceptable consequences in certain people. Clove oil is growing in popularity as an anaesthetic for use on aquarium fish as well as on wild fish when sampled for research and management purposes.

It is one of many compounds that is attractive to males of various species of orchid bees, who apparently gather the chemical to synthesize pheromones; it is commonly used as bait to attract and collect these bees for study. It also attracts female cucumber beetles.

Toxicity

Eugenol is hepatotoxic.Overdose is possible, causing a wide range of symptoms from blood in the patients urine, to convulsions, diarrhea, nausea, unconsciousness, dizziness, or rapid heartbeat. A 2-year old boy nearly died after taking between 5 and 10 ml., according to a published 1993 report.

Some fragrances should be avoided by people with eugenol allergy. An example would be Kouros eau de toilette by Yves Saint Laurent. Eugenol may cause allergic contact dermatitis.

List of plants that contain the chemical

Syzygium aromaticum (cloves)

Cinnamon

Cinnamomum tamala

Myristica fragrans (nutmeg)

Ocimum basilicum

Ocimum gratissimum

Ocimum tenuiflorum (Ocimum sanctum) - Tulsi or Holy Basil

Japanese star anise 

Lemon balm