Chemistry:Eugenol

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Eugenol
Skeletal formula of eugenol
Ball-and-stick model of the eugenol molecule
Names
Preferred IUPAC name
2-Methoxy-4-(prop-2-en-1-yl)phenol
Other names
  • 4-Allyl-2-methoxyphenol
  • 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
Identifiers
3D model (JSmol)
1366759
ChEBI
ChEMBL
ChemSpider
EC Number
  • 202-589-1
KEGG
UNII
Properties
C10H12O2
Molar mass 164.204 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
−1.021×10−4 cm3/mol
Viscosity
  • 9.12 mPa·s at 20 °C
  • 5.99 mPa·s at 30 °C[1]
Hazards
NFPA 704 (fire diamond)
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilHealth code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial 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).
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Infobox references
Tracking categories (test):

Eugenol /ˈjuːdʒɪnɒl/ is an allyl chain-substituted guaiacol, a member of the allylbenzene class of chemical compounds.[2] It is a colorless to pale yellow, aromatic oily liquid extracted from certain essential oils especially from clove, nutmeg, cinnamon, basil and bay leaf.[3][4][5][6] It is present in concentrations of 80–90% in clove bud oil and at 82–88% in clove leaf oil.[7] Eugenol has a pleasant, spicy, clove-like scent.[8] The name is derived from Eugenia caryophyllata, the former Linnean nomenclature term for cloves. The currently accepted name is Syzygium aromaticum.[9]

Biosynthesis

The biosynthesis of eugenol begins with the amino acid tyrosine. L-tyrosine is converted to p-coumaric acid by the enzyme tyrosine ammonia lyase (TAL).[10] From here, p-coumaric acid is converted to caffeic acid by p-coumarate 3-hydroxylase using oxygen and NADPH. S-Adenosyl methionine (SAM) is then used to methylate caffeic acid, forming ferulic acid, which is in turn converted to feruloyl-CoA by the enzyme 4-hydroxycinnamoyl-CoA ligase (4CL).[11] Next, feruloyl-CoA is reduced to coniferaldehyde by cinnamoyl-CoA reductase (CCR). Coniferaldeyhyde is then further reduced to coniferyl alcohol by cinnamyl-alcohol dehydrogenase (CAD) or sinapyl-alcohol dehydrogenase (SAD). Coniferyl alcohol is then converted to an ester in the presence of the substrate CH3COSCoA, forming coniferyl acetate. Finally, coniferyl acetate is converted to eugenol via the enzyme eugenol synthase 1 and the use of NADPH.[citation needed]

File:Eugenol biosynthesis .tif

Pharmacology

Eugenol and thymol possess general anesthetic properties. Like many other anesthetic agents, these 2-alkyl(oxy)phenols act as positive allosteric modulators of the GABAA receptor. Although eugenol and thymol are too toxic and not potent enough to be used clinically, these findings led to the development of 2-substituted phenol anesthetic drugs, including propanidid (later withdrawn) and the widely used propofol.[12] Eugenol and the structurally similar myristicin, have the common property of inhibiting MAO-A and MAO-B in vitro.[13][14]

In humans, complete excretion occurs within 24 hour and metabolites are mostly conjugates of eugenol.[15]

Uses

Humans

Eugenol is used as a flavor or aroma ingredient in teas, meats, cakes, perfumes, cosmetics, flavorings, and essential oils.[2][16][17] It is also used as a local antiseptic and anaesthetic.[18][19] Eugenol can be combined with zinc oxide to form zinc oxide eugenol which has restorative and prosthodontic applications in dentistry. For persons with a dry socket as a complication of tooth extraction, packing the dry socket with a eugenol-zinc oxide paste on iodoform gauze is effective for reducing acute pain.[20] Eugenol-zinc oxide paste is also used for root canal sealing.[21]

Insects and fish

It 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.[22] It also attracts female cucumber beetles.[23]

Eugenol and isoeugenol, which both are floral volatile scent compounds, are catalyzed by a single type of enzyme in the genus Gymnadenia and the gene encoding for this enzyme is the first functionally characterized gene in these species.[24] Eugenol is an ingredient in some insecticides.[2]

Clove oil is common as an anesthetic for use on aquarium fish as well as on wild fish when sampled for research and management purposes.[25][26] Where readily available, it presents a humane method to euthanize sick and diseased fish either by direct overdose or to induce sleep before an overdose of eugenol.[27][28]

Other

Eugenol is an ingredient in some fungicides and weed control products used in agricultural practices in the European Union.[2] It is used in hundreds of household products, such as pesticides, pet care, laundry, cleaning, and paper or vehicle products.[2]

Toxicity

Taken orally in high doses for chronic periods, eugenol may cause liver toxicity.[16] An overdose is possible, causing a wide range of symptoms such as hematuria (blood in urine), convulsions, diarrhea, nausea, unconsciousness, dizziness, tachycardia (rapid heart rate), or acute kidney injury.[16][29] N-acetylcysteine may be used to treat people with eugenol or clove oil overdose.[30]


As an allergenic

Eugenol is subject to restrictions on its use in perfumery[31] as some people may become sensitised to it, however, the degree to which eugenol can cause an allergic reaction in humans is disputed.[32]

Eugenol is a component of balsam of Peru, to which some people are allergic.[33][34] When eugenol is used in dental preparations such as surgical pastes, dental packing, and dental cement, it may cause contact stomatitis and allergic cheilitis.[33] The allergy can be discovered via a patch test.[33]

Natural occurrence

Eugenol naturally occurs in numerous plants, including the following:

  • Wood avens

See also

References

  1. ↑ Bingham, Eugene C.; Spooner, Laurence W. (1932). "The Fluidity Method for the Determination of Association. I". Journal of Rheology 3 (2): 221–244. doi:10.1122/1.2116455. ISSN 0097-0360. Bibcode: 1932JRheo...3..221B. 
  2. ↑ 2.0 2.1 2.2 2.3 2.4 "Eugenol". PubChem, US National Library of Medicine. 16 October 2021. https://pubchem.ncbi.nlm.nih.gov/compound/eugenol. 
  3. ↑ "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. https://www.researchgate.net/publication/228673419. 
  4. ↑ "Investigation of the essential oil of cinnamon leaf grown at Bangalore and Hyderabad". Flavour and Fragrance Journal 10 (4): 239–242. 1995. doi:10.1002/ffj.2730100403. 
  5. ↑ Yield and Oil Composition of 38 Basil (Ocimum basilicum L.) Accessions Grown in Mississippi
  6. ↑ "Typical G.C. for bay leaf oil". Thegoodscentscompany.com. http://www.thegoodscentscompany.com/gca/gc1101071.html. 
  7. ↑ Herbal Medicines (3rd ed.). London: Pharmaceutical Press. 2007. ISBN 978-0-85369-623-0. http://file.zums.ac.ir/ebook/366-Herbal%20Medicines,%20Third%20edition-Joanne%20Barnes%20J.%20David%20Phillipson%20Linda%20A.%20Anderson-085369623.pdf. Retrieved 27 April 2015. 
  8. ↑ Wishart, David S.; Djombou Feunang, Yannick; Marcu, Ana; Guo, An Chi; Liang, Kevin; Vázquez Fresno, Rosa; Sajed, Tanvir; Johnson, Daniel et al.. "Showing metabocard for Eugenol (HMDB0005809)". http://www.hmdb.ca/metabolites/HMDB0005809. 
  9. ↑ "Clove (Syzygium aromaticum): a precious spice". Asian Pacific Journal of Tropical Biomedicine 4 (2): 90–6. February 2014. doi:10.1016/S2221-1691(14)60215-X. PMID 25182278. 
  10. ↑ Dewick, P. M. (2009). Medicinal Natural Products. John Wiley & Sons. doi:10.1002/9780470742761. ISBN 9780470742761. 
  11. ↑ Harakava, R. (2005). "Genes encoding enzymes of the lignin biosynthesis pathway in Eucalyptus". Genet. Mol. Biol. 28 (3 suppl): 601–607. doi:10.1590/S1415-47572005000400015. 
  12. ↑ "Anesthetic Agents of Plant Origin: A Review of Phytochemicals with Anesthetic Activity". Molecules 22 (8): 1369. August 2017. doi:10.3390/molecules22081369. PMID 28820497. 
  13. ↑ "Eugenol and its structural analogs inhibit monoamine oxidase A and exhibit antidepressant-like activity". Bioorganic & Medicinal Chemistry 13 (15): 4777–88. August 2005. doi:10.1016/j.bmc.2005.04.081. PMID 15936201. 
  14. ↑ Tisserand, Robert; Young, Rodney (2013). Essential oil safety : a guide for health care professionals (Second ed.). Edinburgh. p. 73. ISBN 978-0443062414. https://www.sciencedirect.com/topics/pharmacology-toxicology-and-pharmaceutical-science/myristicin. 
  15. ↑ "The metabolism of eugenol in man". Xenobiotica; the Fate of Foreign Compounds in Biological Systems 20 (2): 209–22. February 1990. doi:10.3109/00498259009047156. PMID 2333717. 
  16. ↑ 16.0 16.1 16.2 "Eugenol (clove oil)". LiverTox, US National Institute of Diabetes and Digestive and Kidney Diseases. 28 October 2018. https://www.ncbi.nlm.nih.gov/books/NBK551727/. 
  17. ↑ "Hair loss after Corona vaccination and infection: Chief doctor clarifies". https://www.colcorona.net/de/haarausfall-nach-corona. 
  18. ↑ "Anesthetic action of methyleugenol and other eugenol derivatives". Pharmacology 14 (4): 367–77. 1976. doi:10.1159/000136617. PMID 935250. 
  19. ↑ "Formulation and evaluation of mucoadhesive tablets containing eugenol for the treatment of periodontal diseases". Drug Development and Industrial Pharmacy 30 (2): 195–203. February 2004. doi:10.1081/DDC-120028715. PMID 15089054. 
  20. ↑ "Systemic review of dry socket: aetiology, treatment, and prevention". Journal of Clinical and Diagnostic Research 9 (4): ZE10-3. April 2015. doi:10.7860/JCDR/2015/12422.5840. PMID 26023661. 
  21. ↑ Ferracane, Jack L. (2001). Materials in Dentistry: Principles and Applications (2nd ed.). Lippincott, Williams & Wilkins. ISBN 978-0-7817-2733-4. 
  22. ↑ "Odor compound detection in male euglossine bees". Journal of Chemical Ecology 29 (1): 253–7. January 2003. doi:10.1023/A:1021932131526. PMID 12647866. 
  23. ↑ "Cucumber Beetles: Organic and Biorational Integrated Pest Management (Summary)". Attra.ncat.org. 2013-08-05. http://attra.ncat.org/attra-pub/cucumberbeetle.html. 
  24. ↑ 24.0 24.1 "Eugenol synthase genes in floral scent variation in Gymnadenia species". Functional & Integrative Genomics 14 (4): 779–88. December 2014. doi:10.1007/s10142-014-0397-9. PMID 25239559. https://www.zora.uzh.ch/id/eprint/104915/8/ZORA_NL_104915.pdf. 
  25. ↑ "Anesthesia, Analgesia, and Surgery in Pet Fish". 2001. http://www.vin.com/VINDBPub/SearchPB/Proceedings/PR05000/PR00342.htm. Retrieved 2014-03-17. 
  26. ↑ "The efficacy of clove oil as an anesthetic for the zebrafish, Danio rerio (Hamilton)". Zebrafish 1 (1): 46–53. February 2004. doi:10.1089/154585404774101671. PMID 18248205. 
  27. ↑ Monks, Neale (2009-04-02). "Aquarium Fish Euthanasia". Fish Channel. http://www.fishchannel.com/media/fish-health/euthanasia.aspx.pdf. 
  28. ↑ de Souza Valente, Cecília (June 2022). "Anaesthesia of decapod crustaceans" (in en). Veterinary and Animal Science 16: 100252. doi:10.1016/j.vas.2022.100252. PMID 35620220. 
  29. ↑ "Eugenol Oil Overdose". The New York Times. http://health.nytimes.com/health/guides/poison/eugenol-oil-overdose/overview.html. 
  30. ↑ Janes, S. E.; Price, C. S.; Thomas, D. (2005). "Essential oil poisoning: N-acetylcysteine for eugenol-induced hepatic failure and analysis of a national database". European Journal of Pediatrics 164 (8): 520–522. doi:10.1007/s00431-005-1692-1. PMID 15895251. https://pubmed.ncbi.nlm.nih.gov/15895251/. 
  31. ↑ "IFRA". http://www.ifraorg.org/en-us/standards_restricted/s3/p4. 
  32. ↑ "Cropwatch Claims Victory Regarding "26 Allergens" Legislation". leffingwell.com. http://www.leffingwell.com/Cropwatch%20Claims%20Victory%20Over%2026%20Allergens.pdf. 
  33. ↑ 33.0 33.1 33.2 Schmalz, Gottfried; Bindslev, Dorthe Arenholt (2008). Biocompatibility of Dental Materials. Springer. p. 352. ISBN 978-3-540-77782-3. https://books.google.com/books?id=mrreTHuo54wC&pg=PA352. 
  34. ↑ Bruynzeel, Derk P. (2014). "Balsam of Peru (Myroxylon pereirae)". Management of Positive Patch Test Reactions. Springer. pp. 53–55. doi:10.1007/978-3-642-55706-4_11. ISBN 978-3-540-44347-6. 
  35. ↑ "TLC Densitometric Method for the Quantification of Eugenol and Gallic Acid in Clove". Chromatographia 60 (3–4): 241–244. 2004. doi:10.1365/s10337-004-0373-y. 
  36. ↑ 36.0 36.1 "Inhibition of growth and aflatoxin production by cinnamon and clove oils. Cinnamic aldehyde and eugenol". Journal of Food Science 42 (4): 1107–1109. July 1977. doi:10.1111/j.1365-2621.1977.tb12677.x. 
  37. ↑ Lee, Kwang-Geun; Shibamoto, Takayuki (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. 
  38. ↑ "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): 755–62. September 2000. doi:10.1016/S0278-6915(00)00073-9. PMID 10930696. 
  39. ↑ "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. 2005. doi:10.1365/s10337-005-0527-6. 
  40. ↑ "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. 1988. doi:10.1002/ptr.2650020305. 
  41. ↑ "Substantial UV-B-mediated induction of essential oils in sweet basil (Ocimum basilicum L.)". Phytochemistry 51 (4): 507–510. 1999. doi:10.1016/S0031-9422(98)00767-5. Bibcode: 1999PChem..51..507J. 
  42. ↑ "Antibacterial activity of Ocimum gratissimum L. essential oil". Memórias do Instituto Oswaldo Cruz 94 (5): 675–8. September 1999. doi:10.1590/S0074-02761999000500022. PMID 10464416. 
  43. ↑ "Neurotoxicities in infants seen with the consumption of star anise tea". Pediatrics 114 (5): e653-6. November 2004. doi:10.1542/peds.2004-0058. PMID 15492355. 
  44. ↑ "Lemon balm". University of Maryland Medical Center. http://umm.edu/health/medical/altmed/herb/lemon-balm. 



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