Human Metabolome Database Version 3.5

Showing metabocard for Eugenol (HMDB05809)

Record Information
Version 3.5
Creation Date 2007-01-23 06:27:56 -0700
Update Date 2013-02-08 17:14:21 -0700
HMDB ID HMDB05809
Secondary Accession Numbers None
Metabolite Identification
Common Name Eugenol
Description Eugenol 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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C10H12O2
Average Molecular Weight 164.2011
Monoisotopic Molecular Weight 164.083729628
IUPAC Name 2-methoxy-4-(prop-2-en-1-yl)phenol
Traditional IUPAC Name eugenol
CAS Registry Number 97-53-0
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 Key RRAFCDWBNXTKKO-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Homomonocyclic Compounds
Class Phenols and Derivatives
Sub Class Methoxyphenols and Derivatives
Other Descriptors
  • Aromatic Homomonocyclic Compounds
  • Monolignols(KEGG)
  • a monoterpenol(Cyc)
  • a phenol(Cyc)
  • phenylpropanoid(ChEBI)
Substituents
  • Alkyl Aryl Ether
  • Anisole
Direct Parent Methoxyphenols and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Cosmetic
  • Drug
  • Food
Biofunction Not Available
Application Not Available
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 1.44 g/L ALOGPS
LogP 2.66 ALOGPS
LogP 2.61 ChemAxon
LogS -2.06 ALOGPS
pKa (strongest acidic) 9.94 ChemAxon
pKa (strongest basic) -4.9 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 29.46 A2 ChemAxon
Rotatable Bond Count 3 ChemAxon
Refractivity 48.79 ChemAxon
Polarizability 17.9 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
6.5 +/- 0.03 uM Adult (>18 years old) Both Normal
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID 646 Link_out
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB012171
KNApSAcK ID C00000619 Link_out
Chemspider ID 13876103 Link_out
KEGG Compound ID C10453 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Eugenol Link_out
NuGOwiki Link HMDB05809 Link_out
Metagene Link HMDB05809 Link_out
METLIN ID 4022 Link_out
PubChem Compound 3314 Link_out
PDB ID EOL Link_out
ChEBI ID 4917 Link_out
References
Synthesis Reference Ogiso, 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) Download (PDF)
General References Not Available

Enzymes
Name: UDP-glucuronosyltransferase 2B28
Reactions: Not Available
Gene Name: UGT2B28
Uniprot ID: Q9BY64 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 2B17
Reactions: Not Available
Gene Name: UGT2B17
Uniprot ID: O75795 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA