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22-AUGUST-2008 06:13:22 - Eugenol Eugenol Eugenol Eugenol 3D IUPAC name 4-Allyl-2-methoxyphenol Other names 2-Methoxy-4-2-propenylphenol 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-ylphenol Identifiers CAS number 97-53-0 SMILES Oc1ccccc1OCCC=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 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. Contents 1 Modern uses 2 Toxicity 3 Health Safety information 4 References 5 External links 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.29.5052 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:10.1081/DDC-120028715. 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:10.1093/bja/34.6.379. PMID 14008420. ^ Schiestl FP, Roubik DW 2003 Jan. Odor Compound Detection in Male Euglossine Bees. Journal of Chemical Ecology 29 1: 253-257. doi:10.1023/A:1021932131526. PMID 12647866. ^ Survey and health assessment of chemical substances in massage oils External links Eugenol entry on the Molecule of the Day blog v d e Stomatological preparations A01 Caries prophylactic agents Sodium fluoride - Sodium monofluorophosphate - Olaflur - Stannous fluoride Anti-infectives and antiseptics Hydrogen peroxide - Chlorhexidine - Amphotericin B - Polynoxylin - Domiphen - Oxyquinoline - Neomycin - Miconazole - Natamycin - Hexetidine - Tetracycline - Benzoxonium chloride - Tibezonium iodide - Mepartricin - Metronidazole - Clotrimazole - Sodium perborate - Chlortetracycline - Doxycycline - Minocycline - Eugenol Corticosteroids Glucocorticoids Triamcinolone - Dexamethasone - Hydrocortisone Other Epinephrine/Adrenalone - Benzydamine - Acetylsalicylic acid - Amlexanox Retrieved from http://en..org/wiki/Eugenol Categories: Flavors | Phenols | Alkenes | Phenylpropanoids | Perfume ingredients Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages Dansk Deutsch Español Français Bahasa Indonesia Italiano Nederlands 日本語 Polski Português ไทย This page was last modified on 4 July 2008, at 17:43. of the GNU Free Documentation License. ® , Inc., a U.S.
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