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, basil and bay leaf.[citation needed] It is slightly soluble in water and soluble in organic solvents. It has a pleasant, 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.
[edit] 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, 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. 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 as well as on wild fish when sampled for research and management purposes.
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]
[edit] Toxicity
Eugenol is hepatotoxic.[4][5]
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.[6] A 2-year old boy nearly died after taking between 5 and 10 ml., according to a published 1993 report.[7]
Eugenol should be avoided by people with perfume allergy.[8][clarification needed] Eugenol may cause allergic contact dermatitis with the skin.[9]
[edit] List of plants that contain the chemical
[edit] See also
[edit] References
- ^ Jadhav BK, Khandelwal KR, Ketkar AR, Pisal SS. (February 2004). "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. http://bja.oxfordjournals.org/cgi/content/abstract/34/6/379.
- ^ Schiestl FP, Roubik DW (January 2003). "Odor Compound Detection in Male Euglossine Bees". Journal of Chemical Ecology 29 (1): 253–257. doi:10.1023/A:1021932131526. PMID 12647866. http://springerlink.com/content/kv52574k74438848/.
- ^ Thompson, DC; Barhoumi, R; Burghardt, RC (1998). "Comparative toxicity of eugenol and its quinone methide metabolite in cultured liver cells using kinetic fluorescence bioassays.". Toxicology and applied pharmacology 149 (1): 55–63. doi:10.1006/taap.1997.8348. PMID 9512727.
- ^ Fujisawa, S; Atsumi, T; Kadoma, Y; Sakagami, H (2002). "Antioxidant and prooxidant action of eugenol-related compounds and their cytotoxicity.". Toxicology 177 (1): 39–54. doi:10.1016/S0300-483X(02)00194-4. PMID 12126794.
- ^ Eugenol Oil Overdose, New York Times Health Guide
- ^ Hartnoll, G; Moore, D; Douek, D (1993). "Near fatal ingestion of oil of cloves.". Archives of disease in childhood 69 (3): 392–3. doi:10.1136/adc.69.3.392. PMID 8215554.
- ^ Survey and health assessment of chemical substances in massage oils
- ^ Signs and Symptoms of Eugenol Poisoning http://www.pesticideinfo.org/Detail_Chemical.jsp?Rec_Id=PC33197#Symptoms
- ^ Pathak, S. B. et al.; Niranjan, K.; Padh, H.; Rajani, M. (2004). "TLC Densitometric Method for the Quantification of Eugenol and Gallic Acid in Clove". Chromatographia 60 (3 - 4): 241–244. doi:10.1365/s10337-004-0373-y.
- ^ a b BULLERMAN, L. B. et al.; Lieu, F. Y.; Seier, Sally A. (1977). "INHIBITION OF GROWTH AND AFLATOXIN PRODUCTION BY CINNAMON AND CLOVE OILS. CINNAMIC ALDEHYDE AND EUGENOL". Journal of Food Science 42 (4): 1107–1109. doi:10.1111/j.1365-2621.1977.tb12677.x.
- ^ Lee, Kwang-Geun; Takayuki Shibamoto (2001). "Antioxidant property of aroma extract isolated from clove buds [Syzygium aromaticum (L.) Merr. et Perry]". Food Chemistry 74 (4): 443–448. doi:10.1016/S0308-8146(01)00161-3.
- ^ Kreydiyyeh, S. I. et al.; Usta, J; Copti, R (2000). "Effect of cinnamon, clove and some of their constituents on the Na+-K+-ATPase activity and alanine absorption in the rat jejunum". Food and Chemical Toxicology 38 (9): 755–762. doi:10.1016/S0278-6915(00)00073-9. PMID 10930696.
- ^ Dighe, V. V. et al.; Gursale, A. A.; Sane, R. T.; Menon, S.; Patel, P. H. (2005). "Quantitative Determination of Eugenol from Cinnamomum tamala Nees and Eberm. Leaf Powder and Polyherbal Formulation Using Reverse Phase Liquid Chromatography". Chromatographia 61 (9 - 10): 443–446. doi:10.1365/s10337-005-0527-6.
- ^ Bennett, A. et al.; Stamford, I. F.; Tavares, I. A.; Jacobs, S.; Capasso, F.; Mascolo, N.; Autore, G.; Romano, V. et al. (1988). "The biological activity of eugenol, a major constituent of nutmeg (Myristica fragrans): Studies on prostaglandins, the intestine and other tissues". Phytotherapy Research 2 (3): 124–130. doi:10.1002/ptr.2650020305.
- ^ Johnson, C. B.; Kirby, J.; Naxakis, G.; Pearson, S. (1999). "Substantial UV-B-mediated induction of essential oils in sweet basil (Ocimum basilicum L.)". Phytochemistry 51 (4): 507–510. doi:10.1016/S0031-9422(98)00767-5.
- ^ "Neurotoxicities in Infants Seen With the Consumption of Star Anise Tea". PEDIATRICS 114 (5): e653-e656. 2004. doi:10.1542/peds.2004-0058.
[edit] External links
