Eugenol
| Eugenol |
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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
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| Identifiers |
| CAS number |
97-53-0 Y |
| PubChem |
3314 |
| ChemSpider |
13876103 Y |
| UNII |
3T8H1794QW Y |
| KEGG |
D04117 Y |
| ChEBI |
CHEBI:4917 Y |
| ChEMBL |
CHEMBL42710 Y |
| Jmol-3D images |
Image 1 |
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InChI=1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3,5-7,11H,1,4H2,2H3 Y
Key: RRAFCDWBNXTKKO-UHFFFAOYSA-N Y
InChI=1/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3,5-7,11H,1,4H2,2H3
Key: RRAFCDWBNXTKKO-UHFFFAOYAJ
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| Properties |
| Molecular formula |
C10H12O2 |
| Molar mass |
164.20 g/mol |
| Density |
1.06 g/cm3 |
| Melting point |
-7.5 °C, 266 K, 19 °F
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| Boiling point |
254 °C, 527 K, 489 °F
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| Hazards |
| Flash point |
104 °C |
Y (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
| Infobox references |
Eugenol is a phenylpropene, 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.[1][2][3][4][5] It is slightly soluble in water and soluble in organic solvents. It has a 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.
Modern uses
Eugenol is used in perfumeries, flavorings, essential oils and in medicine as a local antiseptic and anesthetic.[6]
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.
Eugenol can be combined with zinc oxide to form a material - known as zinc oxide eugenol - which has restorative and prosthodontic applications in dentistry.[7]
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.
It can be used to reduce the presence of Listeria monocytogenes and Lactobacillus sakei in food.[8]
They are also used in manufacturing stabilizers and antioxidants for plastics and rubbers. Attempts have been made to develop eugenol derivatives for intravenous injection, such as propanidid and G.29.505. The latter produced unacceptable side effects around the site of injection in many patients.[9]
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.[10] It also attracts female cucumber beetles.[11]
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[12][13] where, readily available over-the-counter from pharmacies, it may be a humane method to euthanise sick and diseased fish either by direct over-dose or to induce sleep before an overdose of ethanol.[14]
It is also used in some mousetraps.[15]
Eugenol kills certain human colon cancer cell lines in vitro.[16]
Toxicity
Eugenol is hepatotoxic, meaning it may cause damage to the liver.[17][18]
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.[19] A 2-year old boy nearly died after taking between 5 and 10 ml., according to a published 1993 report.[20]
Some fragrances should be avoided by people with eugenol allergy.[21] An example would be Kouros eau de toilette by Yves Saint Laurent.[22] Eugenol may cause allergic contact dermatitis.[23]
List of plants that contain the chemical
See also
References
- ^ Constituents of the essential oil from leaves and buds of clove (Syzigium caryophyllatum (L.) Alston
- ^ Typical G.C. for nutmeg oil
- ^ Investigation of the essential oil of cinnamon leaf grown at Bangalore and Hyderabad
- ^ Yield and Oil Composition of 38 Basil (Ocimum basilicum L.) Accessions Grown in Mississippi
- ^ Typical G.C. for bay leaf oil
- ^ 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.
- ^ Jack L. Ferracane, Materials in Dentistry: Principles and Applications, 2001, 2d Edition, Lippincott Williams & Wilkins, ISBN 0781727332
- ^ Mechanisms of Bactericidal Action of Cinnamaldehyde against Listeria monocytogenes and of Eugenol against L. monocytogenes and Lactobacillus sakei. Alexander O. Gill and Richard A. Holley, Appl. Environ. Microbiol., October 2004, vol. 70, no. 10, pages 5750-5755, doi:10.1128/AEM.70.10.5750-5755.2004
- ^ 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 (6): 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/.
- ^ http://attra.ncat.org/attra-pub/cucumberbeetle.html
- ^ http://www.vin.com/VINDBPub/SearchPB/Proceedings/PR05000/PR00342.htm
- ^ http://www.liebertonline.com/doi/abs/10.1089/154585404774101671
- ^ Monks, Neale, Ph.D. (2009-04-02). "Aquarium Fish Euthanasia". Fish Channel. http://www.fishchannel.com/media/fish-health/euthanasia.aspx.pdf. Retrieved 2010-12-07.
- ^ http://www.lowes.com/pd_188374-30313-32411_0_
- ^ Jaganathan, SK; Mazumdar, A; Mondhe, D; Mandal, M (2011). "Apoptotic effect of eugenol in human colon cancer cell lines". Cell biology international 35 (6): 607–15. doi:10.1042/CBI20100118. PMID 21044050.
- ^ 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. PMC 1029532. PMID 8215554. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1029532.
- ^ http://www.wrongdiagnosis.com/n/non_food_allergy_eugenol/intro.htm
- ^ http://www.yslbeautyus.com/mens-fragrance-kouros-fragrance/c37_63_84/p282/kouros-eau-de-toilette-spray/product_info.html
- ^ Signs and Symptoms of Eugenol Poisoning http://www.pesticideinfo.org/Detail_Chemical.jsp?Rec_Id=PC33197#Symptoms
- ^ Pathak, S. B. et al. (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. (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. (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. (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. (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.
- ^ Celso Vataru Nakamura, Tania Ueda-Nakamura, Erika Bando, Abrahão Fernandes Negrão Melo, Díogenes Aparício Garcia Cortez, Benedito Prado Dias Filho, "Antibacterial Activity of Ocimum gratissimum L. Essential Oil", Memórias do Instituto Oswaldo Cruz, Vol. 94(5): 675–678.
- ^ "Neurotoxicities in Infants Seen With the Consumption of Star Anise Tea". Pediatrics 114 (5): e653–e656. 2004. doi:10.1542/peds.2004-0058. PMID 15492355.
- ^ "Lemon balm". University of Maryland Medical Center. http://www.umm.edu/altmed/articles/lemon-balm-000261.htm. Retrieved 2010-12-07.
External links
- Kegley, S.E., Hill, B.R., Orme S., Choi A.H., Toxicity Information for Eugenol in PAN Pesticide Database, Pesticide Action Network, North America (San Francisco, CA, 2010)
- "Eugenol (Mmm, dentist) : Molecule of the Day". ScienceBlogs. 2006-10-04. http://scienceblogs.com/moleculeoftheday/2006/10/eugenol_mmm_dentist.php#commentsArea. Retrieved 2010-12-07. (Eugenol entry on the Molecule of the Day blog)