Eugenol

Eugenol
Skeletal formula of eugenol
Ball-and-stick model of the eugenol molecule
Names
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
97-53-0 YesY
ChEBI CHEBI:4917 YesY
ChEMBL ChEMBL42710 YesY
ChemSpider 13876103 YesY
2425
Jmol 3D model Interactive image
KEGG D04117 YesY
PubChem 3314
UNII 3T8H1794QW YesY
Properties
C10H12O2
Molar mass 164.20 g·mol−1
Density 1.06 g/cm3
Melting point −7.5 °C (18.5 °F; 265.6 K)
Boiling point 254 °C (489 °F; 527 K)
Acidity (pKa) 10.19 at 25 °C
Hazards
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
1
2
0
Flash point 104 °C (219 °F; 377 K)
Related compounds
Related compounds
 2-Phenethyl propionate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

Eugenol /juːɡɛnɒl/ is a phenylpropene, an allyl chain-substituted guaiacol. Eugenol is a member of the phenylpropanoids class of chemical compounds. It is a colourless to pale yellow oily liquid extracted from certain essential oils especially from clove oil, nutmeg, cinnamon, basil and bay leaf.[1][2][3][4] It is present in concentrations of 80–90% in clove bud oil and at 82–88% in clove leaf oil.[5]

Modern uses

Eugenol is used in perfumes, flavorings, and essential oils. It is also as a local antiseptic and anaesthetic.[6] Eugenol can be combined with zinc oxide to form a material – known as zinc oxide eugenol – which has restorative and prosthodontic applications in dentistry. For example, zinc oxide eugenol is used for root canal sealing.[7]

Attempts have been made to develop eugenol derivatives as intravenous anesthetics, as an alternative to propanidid which produces unacceptable side effects around the site of injection in many patients.[8]

It can be used to reduce the presence of Listeria monocytogenes and Lactobacillus sakei in food.[9]

It is also used in manufacturing stabilizers and antioxidants for plastics and rubbers.

It is one of many compounds that is attractive to males of various species of orchid bees, which 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 beetle.[11] It is recently discovered that eugenol and isoeugenol, floral volatile scent compounds, are catalyzed by single type of enzyme in Gymnadenia species and gene encoding for this enzyme is first functionally characterized gene in this species so far.[12]

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.[13][14] Where readily available, it presents a humane method to euthanise sick and diseased fish either by direct over-dose or to induce sleep before an overdose of ethanol.[15]

It is also used in some mousetraps.

Toxicity

Eugenol is hepatotoxic, meaning it may cause damage to the liver.[16][17] Overdose is possible, causing a wide range of symptoms from blood in the patient's urine, to convulsions, diarrhoea, nausea, unconsciousness, dizziness, or rapid heartbeat.[18] According to a published 1993 report, a 2-year-old boy nearly died after taking between 5 and 10 ml.[19] Eugenol is subject to restrictions on its use in perfumery[20] as some people may become sensitised to it, however, the degree to which eugenol can cause an allergic reaction in humans is disputed.[21]

Allergy

Eugenol is a component of Balsam of Peru, to which some people are allergic.[22][23] When eugenol is used in dental preparations such as surgical pastes, dental packing, and dental cement, it may cause contact stomatitis and allergic cheilitis.[22] The allergy can be discovered via a patch test.[22]

List of plants that contain the chemical

See also

References

  1. ↑ "Constituents of the essential oil from leaves and buds of clove (Syzigium caryophyllatum (L.) Alston" (PDF). Bangladesh Council of Scientific and Industrial Research BCSIR Laboratories 4: 451–454.
  2. ↑ Mallavarapu, Gopal R.; Ramesh, S.; Chandrasekhara, R. S.; Rajeswara Rao, B. R.; Kaul, P. N.; Bhattacharya, A. K. (1995). "Investigation of the essential oil of cinnamon leaf grown at Bangalore and Hyderabad". Flavour and Fragrance Journal (wiley.com) 10 (4): 239. doi:10.1002/ffj.2730100403. Retrieved 2014-04-27.
  3. ↑ Yield and Oil Composition of 38 Basil (Ocimum basilicum L.) Accessions Grown in Mississippi Archived 15 October 2010 at the Wayback Machine.
  4. ↑ "Typical G.C. for bay leaf oil". Thegoodscentscompany.com. Retrieved 2014-04-27.
  5. ↑ Barnes, J; Anderson, LA; Phillipson, JD (2007) [1996]. Herbal Medicines (PDF) (3rd ed.). London, UK: Pharmaceutical Press. ISBN 978-0-85369-623-0.
  6. ↑ Jadhav BK, Khandelwal KR, Ketkar AR, Pisal SS.; Khandelwal; Ketkar; Pisal (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.
  7. ↑ Jack L. Ferracane (2001). Materials in Dentistry: Principles and Applications (2nd ed.). Lippincott Williams & Wilkins. ISBN 0-7817-2733-2.
  8. ↑ Right DA, Payne JP; Payne (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.
  9. ↑ Gill, A. O.; Holley, R. A. (2004). "Mechanisms of Bactericidal Action of Cinnamaldehyde against Listeria monocytogenes and of Eugenol against L. Monocytogenes and Lactobacillus sakei". Applied and Environmental Microbiology 70 (10): 5750. doi:10.1128/AEM.70.10.5750-5755.2004. PMID 15466510.
  10. ↑ Schiestl FP, Roubik DW; Roubik (January 2003). "Odor Compound Detection in Male Euglossine Bees". Journal of Chemical Ecology 29 (1): 253–257. doi:10.1023/A:1021932131526. PMID 12647866.
  11. ↑ "Cucumber Beetles: Organic and Biorational Integrated Pest Management (Summary)". Attra.ncat.org. 2013-08-05. Retrieved 2014-04-27.
  12. 1 2 Gupta A K, Schauvinhold I, Pichersky E, and Schiestl F P (2014). "Eugenol synthase genes in floral scent variation in Gymnadenia species". Functional & Integrative Genomics 14 (4): 779–88. doi:10.1007/s10142-014-0397-9. PMID 25239559.
  13. ↑ Anesthesia, Analgesia, and Surgery in Pet Fish. Atlantic Coast Veterinary Conference. 2001. Retrieved 17 March 2014.
  14. ↑ Grush, J; Noakes, DLG; Moccia, RD (February 2004). "The Efficacy of Clove Oil As An Anesthetic for the Zebrafish". Zebrafish 1 (1): 46–53. doi:10.1089/154585404774101671. PMID 18248205.
  15. ↑ Monks, Neale, Ph.D. (2009-04-02). "Aquarium Fish Euthanasia" (PDF). Fish Channel. Retrieved 2010-12-07.
  16. ↑ 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.
  17. ↑ 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.
  18. ↑ Eugenol Oil Overdose, New York Times Health Guide
  19. ↑ 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.
  20. ↑ www.ifraorg.org Archived 30 December 2011 at the Wayback Machine.
  21. ↑ "." (PDF). www.leffingwell.com. Retrieved 2014-04-27.
  22. 1 2 3 Gottfried Schmalz, Dorthe Arenholt Bindslev (2008-10-10). Biocompatibility of Dental Materials. ISBN 9783540777823. Retrieved 2014-04-27.
  23. ↑ Derk P. Bruynzeel (2014). "Management of Positive Patch Test Reactions". Springer: 53. doi:10.1007/978-3-642-55706-4_11. ISBN 978-3-540-44347-6. Retrieved 2014-04-27. |chapter= ignored (help)
  24. ↑ Pathak, SB; 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.
  25. 1 2 Bullerman, LB; Lieu, FY; Seier, SA (July 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.
  26. ↑ 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.
  27. ↑ Kreydiyyeh, SI; Usta, J; Copti, Rtitle = Effect of cinnamon, clove and some of their constituents on the Na+-K+-ATPase activity and alanine absorption in the rat jejunum (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.
  28. ↑ Dighe, VV; Gursale, AA; Sane, RT; Menon, S; Patel, PH (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.
  29. ↑ Bennett, A; Stamford, IF; Tavares, IA; Jacobs, S; Capasso, F; Mascolo, N; Autore, G; Romano, V; Di Carlo, G (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.
  30. ↑ Johnson, CB; 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.
  31. ↑ Nakamura, CV; Ueda-Nakamura, T; Bando, E; Melo, AFN; Cortez, DAG; Dias Filho, BP (September 1999). "Antibacterial activity of Ocimum gratissimum L. essential oil" (PDF). Memórias do Instituto Oswaldo Cruz 94 (5): 675–678. doi:10.1590/S0074-02761999000500022. PMID 10464416.
  32. ↑ Ize-Ludlow, D; Ragone, S; Bruck, IS; Bernstein, JN; Duchowny, M; Peña, BM (2004). "Neurotoxicities in Infants Seen With the Consumption of Star Anise Tea". Pediatrics 114 (5): e653–e656. doi:10.1542/peds.2004-0058. PMID 15492355.
  33. ↑ "Lemon balm". University of Maryland Medical Center. Retrieved 2010-12-07.

External links

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