Eugenol
| Eugenol | |
|---|---|
 | |
 | |
| 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] |
| SMILES |
Oc1ccc(cc1OC)CC=C |
| 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 disclaimer and references | |
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.
Modern uses
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, the toxicity of propanidid and G.29.505[2] in human patients was not acceptable. 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]
Toxicity
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.
Health & Safety information
Eugenol should be avoided by people with perfume allergy.[4]
References
- Jadhav BK, Khandelwal KR, Ketkar AR, Pisal SS. (2004 Feb). "Formulation and evaluation of mucoadhesive tablets containing eugenol for the treatment of periodontal diseases". Drug Dev Ind Pharm. 30 (2): 195–203. doi:. PMID 15089054.
- Right DA, Payne JP (June 1962). "A clinical study of intravenous anaesthesia with a eugenol derivative, G.29.505" (abstract). British Journal of Anaesthesia, 34: 379–385. doi:. PMID 14008420.
- Schiestl FP, Roubik DW (2003 Jan). "Odor Compound Detection in Male Euglossine Bees". Journal of Chemical Ecology 29 (1): 253–257. doi:. PMID 12647866.
- Survey and health assessment of chemical substances in massage oils
External links
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Source: adapted by the editor from Wikipedia, the free encyclopedia; from the article "Eugenol". Image Credit.
