Record Information
Version3.6
Creation Date2007-01-23 13:27:56 UTC
Update Date2013-02-09 00:14:21 UTC
HMDB IDHMDB05809
Secondary Accession NumbersNone
Metabolite Identification
Common NameEugenol
DescriptionEugenol is an allyl chain-substituted guaiacol, i.e. 2-methoxy-4-(2-propenyl)phenol. Eugenol is a member of the allylbenzene class of chemical compounds. It is a clear to pale yellow oily liquid extracted from certain essential oils especially from clove oil, nutmeg, cinnamon, and bay leaf. It is slightly soluble in water and soluble in organic solvents. It has a pleasant, spicy, clove-like odor. Eugenol is used in perfumeries, flavorings, essential oils and in medicine as a local antiseptic and anaesthetic. It was used in the production of isoeugenol for the manufacture of vanillin, though most vanillin is now produced from petrochemicals or from by-products of paper manufacture (Wikipedia).
Structure
Thumb
Synonyms
  1. 1-Hydroxy-2-methoxy-4-allylbenzene
  2. 1-Hydroxy-2-methoxy-4-prop-2-enylbenzene
  3. 1-Hydroxy-2-methoxy-4-propenylbenzene
  4. 2-Hydroxy-5-allylanisole
  5. 2-Methoxy-1-hydroxy-4-allylbenzene
  6. 2-Methoxy-4-(2-propenyl)phenol
  7. 2-Methoxy-4-(3-propenyl)phenol
  8. 2-Methoxy-4-(prop-2-en-1-yl)phenol
  9. 2-Methoxy-4-allylphenol
  10. 2-Methoxy-4-prop-2-enylphenol
  11. 4-Allyl-1-hydroxy-2-methoxybenzene
  12. 4-Allyl-2-methoxy-Phenol
  13. 4-Allyl-2-methoxyphenol
  14. 4-Allylcatechol 2-methyl ether
  15. 4-Allylcatechol-2-methyl ether
  16. 4-Allylguaiacol
  17. 4-Hydroxy-3-methoxy-1-allylbenzene
  18. 4-Hydroxy-3-methoxyallylbenzene
  19. 5-Allylguaiacol
  20. Allylguaiacol
  21. Caryophyllic acid
  22. Engenol
  23. Eugenic acid
  24. Eugenol
  25. Eugenol (natural)
  26. Eugenol [usan]
  27. P-Allylguaiacol
  28. P-Eugenol
  29. Synthetic eugenol
Chemical FormulaC10H12O2
Average Molecular Weight164.2011
Monoisotopic Molecular Weight164.083729628
IUPAC Name2-methoxy-4-(prop-2-en-1-yl)phenol
Traditional IUPAC Nameeugenol
CAS Registry Number97-53-0
SMILES
COC1=C(O)C=CC(CC=C)=C1
InChI Identifier
InChI=1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3,5-7,11H,1,4H2,2H3
InChI KeyRRAFCDWBNXTKKO-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAromatic Homomonocyclic Compounds
ClassPhenols and Derivatives
Sub ClassMethoxyphenols and Derivatives
Other Descriptors
  • Aromatic Homomonocyclic Compounds
  • Monolignols(KEGG)
  • a monoterpenol(Cyc)
  • a phenol(Cyc)
  • phenylpropanoid(ChEBI)
Substituents
  • Alkyl Aryl Ether
  • Anisole
Direct ParentMethoxyphenols and Derivatives
Ontology
StatusDetected and Quantified
Origin
  • Cosmetic
  • Drug
  • Food
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility1.44 g/LALOGPS
logP2.66ALOGPS
logP2.61ChemAxon
logS-2.1ALOGPS
pKa (strongest acidic)9.94ChemAxon
pKa (strongest basic)-4.9ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count2ChemAxon
hydrogen donor count1ChemAxon
polar surface area29.46ChemAxon
rotatable bond count3ChemAxon
refractivity48.79ChemAxon
polarizability17.9ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified6.5 +/- 0.03 uMAdult (>18 years old)BothNormal
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound ID646
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB012171
KNApSAcK IDC00000619
Chemspider ID13876103
KEGG Compound IDC10453
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEugenol
NuGOwiki LinkHMDB05809
Metagene LinkHMDB05809
METLIN ID4022
PubChem Compound3314
PDB IDEOL
ChEBI ID4917
References
Synthesis ReferenceOgiso, Akira; Kobayashi, Shinsaku. a-Vinylbenzylalcohol derivatives. Jpn. Kokai Tokkyo Koho (1974), 6 pp. CODEN: JKXXAF JP 49036644 19740405 Showa. CAN 82:16534 AN 1975:16534
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Gene Name:
UGT2B28
Uniprot ID:
Q9BY64
Gene Name:
UGT2B17
Uniprot ID:
O75795