Eugenol

Eugenol is a phenylpropene, 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 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. Attempts have been made to develop eugenol derivatives for intravenous injection, such as propanidid and G.29.505. The latter produced unacceptable side effects around the site of injection in many patients.

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.

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 where, readily available over-the-counter from pharmacies, it may be a humane method to euthanise sick and diseased fish either by direct over-dose or to induce sleep before an overdose of ethanol.

It is also used in some mousetraps.

Eugenol kills certain human colon cancer cell lines in vitro.

Toxicity
Eugenol is hepatotoxic, meaning it may cause damage to the liver.

Overdose is possible, causing a wide range of symptoms from blood in the patient's 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

 * Cloves (Syzygium aromaticum)
 * Cinnamon
 * Cinnamomum tamala
 * Nutmeg (Myristica fragrans)
 * Ocimum basilicum – Sweet Basil
 * Ocimum gratissimum – African Basil
 * Ocimum tenuiflorum (Ocimum sanctum) – Tulsi or Holy Basil
 * Japanese star anise


 * Lemon balm


 * Dill