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
ECHA InfoCard
 100.002.355 Edit this at Wikidata
EC Number
  • 202-589-1
IUPHAR/BPS
KEGG
UNII
  • InChI=1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3,5-7,11H,1,4H2,2H3 checkY
    Key: RRAFCDWBNXTKKO-UHFFFAOYSA-N checkY
  • 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 164.204 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)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
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 checkY☒N ?)

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

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
]

Biosynthesis of eugenol

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,

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

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

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. ISSN 0097-0360
    .
  2. ^ a b c d e "Eugenol". PubChem, US National Library of Medicine. 16 October 2021. Retrieved 24 October 2021.
  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.
  4. doi:10.1002/ffj.2730100403
    .
  5. ^ Yield and Oil Composition of 38 Basil (Ocimum basilicum L.) Accessions Grown in Mississippi Archived 15 October 2010 at the Wayback Machine
  6. ^ "Typical G.C. for bay leaf oil". Thegoodscentscompany.com. Archived from the original on 17 March 2014. Retrieved 27 April 2014.
  7. ISBN 978-0-85369-623-0. Archived from the original
    (PDF) on 1 July 2018. Retrieved 27 April 2015.
  8. Human Metabolome Database, HMDB
    . 5.0.
  9. PMID 25182278
    .
  10. ISBN 9780470742761
    .
  11. doi:10.1590/S1415-47572005000400015
    .
  12. PMID 28820497
    .
  13. PMID 15936201
    .
  14. ISBN 978-0443062414. Archived from the original on 17 December 2020.{{cite book}}: CS1 maint: location missing publisher (link
    )
  15. PMID 2333717
    .
  16. ^
    PMID 31869191
    . Retrieved 24 October 2021.
  17. ^ "Hair loss after Corona vaccination and infection: Chief doctor clarifies". www.colcorona.net. Retrieved 10 December 2022.
  18. PMID 935250
    .
  19. S2CID 19138725
    .
  20. PMID 26023661
    .
  21. ISBN 978-0-7817-2733-4
    .
  22. S2CID 2845587
    .
  23. ^ "Cucumber Beetles: Organic and Biorational Integrated Pest Management (Summary)". Attra.ncat.org. 5 August 2013. Archived from the original on 16 May 2010. Retrieved 27 April 2014.
  24. ^
    S2CID 17207240
    .
  25. ^ Anesthesia, Analgesia, and Surgery in Pet Fish. Atlantic Coast Veterinary Conference. 2001. Archived from the original on 5 March 2009. Retrieved 17 March 2014.
  26. PMID 18248205
    .
  27. ^ Monks, Neale (2 April 2009). "Aquarium Fish Euthanasia" (PDF). Fish Channel. Archived from the original (PDF) on 26 July 2011. Retrieved 7 December 2010.
  28. PMID 35620220
    .
  29. ^ "Eugenol Oil Overdose". The New York Times. Archived from the original on 25 July 2011.
  30. S2CID 6452985
    .
  31. ^ "IFRA". www.ifraorg.org. Archived from the original on 30 December 2011.
  32. ^ "Cropwatch Claims Victory Regarding "26 Allergens" Legislation" (PDF). leffingwell.com. Archived from the original (PDF) on 10 February 2014. Retrieved 27 April 2014.
  33. ^
    ISBN 978-3-540-77782-3
    .
  34. ISBN 978-3-540-44347-6
    .
  35. S2CID 95396304
    .
  36. ^
    doi:10.1111/j.1365-2621.1977.tb12677.x
    .
  37. doi:10.1016/S0308-8146(01)00161-3
    .
  38. PMID 10930696
    .
  39. S2CID 97399632
    .
  40. S2CID 85114864
    .
  41. doi:10.1016/S0031-9422(98)00767-5
    .
  42. PMID 10464416
    .
  43. PMID 15492355
    .
  44. ^ "Lemon balm". University of Maryland Medical Center. Archived from the original on 1 August 2013. Retrieved 7 December 2020.
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