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Eugenol
From Wikipedia, the free encyclopedia
| Eugenol | |
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| General | |
| Systematic name | Eugenol |
| Other names | 2-Methoxy-4-(2-propenyl)phenol Allylguaiacol 4-Allyl-2-methoxyphenol Eugenic acid Caryophyllic acid 1-Allyl-3-methoxy-4-hydroxybenzene 5-Allylguaiacol 2-Methoxy-4-allylphenol 4-Allylguaiacol 4-allylcatechol-2-methyl ether 4-allyl-1-hydroxy-2-methoxybenzene 1-hydroxy-2-methoxy- 4-prop-2-enylbenzene 1,3,4-eugenol 1-hydroxy-2-methoxy-4-allylbenzene 4-hydroxy-3-methoxyallylbenzene 2-methoxy -1-hydroxy-4-allylbenzene 1-allyl-4-hydroxy-3-methoxybenzene 1-hydroxy-4-allyl-2-methoxybenzene 1-hydroxy-2-methoxy-4-propenylbenzene 2-methoxy-4-(2-propen-1-yl)phenol |
| Molar mass | 164.20 g/mol |
| Melting point | -9 °C |
| Boiling point | 256 °C |
| Density | 1.06 g/cm3 |
| Flash point | 104 °C |
| CAS Number | 97-53-0 |
| Except where noted otherwise, data are given for materials in their standard state (at 25°C, 100 kPa) Infobox disclaimer and references |
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Eugenol (C10H12O2), is an allyl chain-substituted guaiacol, i.e. 2-methoxy-4-(2-propenyl)phenol. Eugenol is a member of the allylbenzene 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 odor.
Eugenol is used in perfumeries, flavorings, essential oils and in medicine as a local antiseptic and anaesthetic. It was used in the production of isoeugenol for the manufacture of vanillin, though most vanillin is now produced from phenol or from lignan.
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. Clove oil is growing in popularity as an anaesthetic for use on aquarium fish.
Eugenol is also used clandestinely for the synthesis of phenethylamines (like MDMA).
Also, the main biologically active compounds in clove cigarettes are eugenol and nicotine.
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. When contact with skin occurs it can cause allergic contact dermatitis.