Eugenol (CHEM003835)

Record Information
Version1.0
Creation Date2014-09-11 05:20:33 UTC
Update Date2026-05-14 19:02:22 UTC
Accession NumberCHEM003835
Identification
Common NameEugenol
ClassSmall Molecule
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).
Contaminant Sources
  • Cosmetic Chemicals
  • EAFUS Chemicals
  • FooDB Chemicals
  • HPV EPA Chemicals
  • IARC Carcinogens Group 3
  • My Exposome Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • Tobacco Smoke Compounds
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Ether
  • Food Toxin
  • Household Toxin
  • Human Neurotoxin
  • Industrial/Workplace Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
  • PFAS
  • Phytotoxin
  • Plant Toxin
  • Solvent
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,3,4-EugenolChEBI
1-Allyl-3-methoxy-4-hydroxybenzeneChEBI
1-Allyl-4-hydroxy-3-methoxybenzeneChEBI
1-Hydroxy-2-methoxy-4-allylbenzeneChEBI
1-Hydroxy-2-methoxy-4-prop-2-enylbenzeneChEBI
1-Hydroxy-2-methoxy-4-propenylbenzeneChEBI
2-Hydroxy-5-allylanisoleChEBI
2-Methoxy-1-hydroxy-4-allylbenzeneChEBI
2-Methoxy-4-(2-propen-1-yl)phenolChEBI
2-Methoxy-4-(2-propenyl)phenolChEBI
2-Methoxy-4-allylphenolChEBI
2-Methoxy-4-prop-2-enyl-phenolChEBI
2-Methoxy-4-prop-2-enylphenolChEBI
4-Allyl-1-hydroxy-2-methoxybenzeneChEBI
4-Allyl-2-methoxyphenolChEBI
4-Allylcatechol-2-methyl etherChEBI
4-AllylguaiacolChEBI
4-Hydroxy-3-methoxy-1-allylbenzeneChEBI
AllylguaiacolChEBI
Caryophyllic acidChEBI
Eugenic acidChEBI
p-AllylguaiacolChEBI
p-EugenolChEBI
CaryophyllateGenerator
EugenateGenerator
2-Methoxy-4-(3-propenyl)phenolHMDB
2-Methoxy-4-(prop-2-en-1-yl)phenolHMDB
4-Allyl-2-methoxy-phenolHMDB
4-Allylcatechol 2-methyl etherHMDB
4-Hydroxy-3-methoxyallylbenzeneHMDB
5-AllylguaiacolHMDB
EngenolHMDB
Eugenol (natural)HMDB
Synthetic eugenolHMDB
2-Methoxy-4-(2'-propenyl)phenolPhytoBank
2-Methoxy-4-(2’-propenyl)phenolPhytoBank
2-Methoxy-4-[2-allyl]phenolPhytoBank
3-(3-Methoxy-4-hydroxyphenyl)propenePhytoBank
3-(4-Hydroxy-3-methoxyphenyl)-1-propenePhytoBank
4-AllenylguaiacolPhytoBank
Chemical FormulaC10H12O2
Average Molecular Mass164.201 g/mol
Monoisotopic Mass164.084 g/mol
CAS Registry Number97-53-0
IUPAC Name2-methoxy-4-(prop-2-en-1-yl)phenol
Traditional Nameeugenol
SMILESCOC1=C(O)C=CC(CC=C)=C1
InChI IdentifierInChI=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
Description Belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassMethoxyphenols
Direct ParentMethoxyphenols
Alternative Parents
Substituents
  • Methoxyphenol
  • Phenoxy compound
  • Methoxybenzene
  • Phenol ether
  • Anisole
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point-7.5°C (18.5°F)
Boiling Point253.2°C (487.8°F)
SolubilityNot 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 Area29.46 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity48.79 m³·mol⁻¹ChemAxon
Polarizability17.9 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)3, not classifiable as to its carcinogenicity to humans. (1)
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDDB09086
HMDB IDHMDB0005809
FooDB IDFDB012171
Phenol Explorer ID646
KNApSAcK IDC00000619
BiGG IDNot Available
BioCyc IDCPD-6481
METLIN ID4022
PDB IDEOL
Wikipedia LinkEugenol
Chemspider ID13876103
ChEBI ID4917
PubChem Compound ID3314
Kegg Compound IDC10453
YMDB IDYMDB01613
ECMDB IDNot Available
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
MSDSLink
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11033063
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11806158
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=14745850
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=15574415
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=18218839
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=20809147
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=22075131
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=22923067
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=23181601
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=23261812
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=23264268
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=2329164
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=23313798
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=23325490
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=23422484
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=23422489
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=23444040
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=23594212
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=23666640
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=23677922
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=23707945
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=23768603
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=23768604
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=23791894
25. https://www.ncbi.nlm.nih.gov/pubmed/?term=23837051
26. https://www.ncbi.nlm.nih.gov/pubmed/?term=23841789
27. https://www.ncbi.nlm.nih.gov/pubmed/?term=23852671
28. https://www.ncbi.nlm.nih.gov/pubmed/?term=28044068
29. https://www.ncbi.nlm.nih.gov/pubmed/?term=29079364
30. https://www.ncbi.nlm.nih.gov/pubmed/?term=32737935
31. https://www.ncbi.nlm.nih.gov/pubmed/?term=33291666
32. https://www.ncbi.nlm.nih.gov/pubmed/?term=33916044
33. https://www.ncbi.nlm.nih.gov/pubmed/?term=8596779
34. https://www.ncbi.nlm.nih.gov/pubmed/?term=9084914
35. 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