| Eugenol | |
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| IUPAC name | 4-Allyl-2-methoxyphenol |
| Other names | 2-Methoxy-4-(2-propenyl)phenol Eugenic acid Caryophyllic acid 1-Allyl-3-methoxy-4-hydroxybenzene Allylguaiacol 2-Methoxy-4-allylphenol 4-Allylcatechol-2-methyl ether 2-methoxy-4-(2-propen-1-yl)phenol |
| Identifiers | |
| CAS number | [97-53-0] |
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| Properties | |
| Molar mass | 164.20 g/mol |
| Density | 1.06 g/cm3 |
| Melting point |
-9 °C, 264 K, 16 °F |
| Boiling point |
256 °C, 529 K, 493 °F |
| Hazards | |
| Flash point | 104 °C |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox references |
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Eugenol (C10H12O2), 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, and bay leaf. It is slightly soluble in water and soluble in organic solvents. It has a pleasant, spicy, clove-like aroma.
The name comes from a scientific name for the 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.
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Eugenol is used in perfumeries, flavorings, essential oils and in medicine as a local antiseptic and anesthetic.[1] 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, zinc oxide eugenol forms 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.[2] Clove oil is growing in popularity as an anaesthetic for use on aquarium fish.
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.[3]
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. Eugenol may cause allergic contact dermatitis with the skin.
Eugenol should be avoided by people with perfume allergy.[4]
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