Eugenol

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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
  • InChI=1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3,5-7,11H,1,4H2,2H3 YesY
    Key: RRAFCDWBNXTKKO-UHFFFAOYSA-N YesY
  • 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
  • Oc1ccc(cc1OC)CC=C
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
Vapor pressure {{{value}}}
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 colorless 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 perfumeries, flavorings, and essential oils. It is also as a local antiseptic and anaesthetic.[6][unreliable medical source?] 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.[citation needed]

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

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See also

References

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External links

  • Kegley, SE; Hill, BR; Orme S; Choi AH; Toxicity Information for Eugenol in PAN Pesticide Database, Pesticide Action Network, North America (San Francisco, CA, 2010)
  • Lua error in package.lua at line 80: module 'strict' not found. (Eugenol entry on the Molecule of the Day blog)
  1. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  2. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ Yield and Oil Composition of 38 Basil (Ocimum basilicum L.) Accessions Grown in Mississippi Archived 15 October 2010 at the Wayback Machine
  4. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  6. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  7. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  8. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  9. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  10. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  11. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  12. ↑ 12.0 12.1 Lua error in package.lua at line 80: module 'strict' not found.
  13. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  14. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  15. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  16. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  17. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  18. ↑ Eugenol Oil Overdose, New York Times Health Guide
  19. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  20. ↑ www.ifraorg.org Archived 30 December 2011 at the Wayback Machine
  21. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  22. ↑ 22.0 22.1 22.2 Lua error in package.lua at line 80: module 'strict' not found.
  23. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  24. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  25. ↑ 25.0 25.1 Lua error in package.lua at line 80: module 'strict' not found.
  26. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  27. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  28. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  29. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  30. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  31. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  32. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  33. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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