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Record Information
Version3.6
Creation Date2007-01-22 22:53:28 UTC
Update Date2016-02-11 01:07:17 UTC
HMDB IDHMDB05802
Secondary Accession NumbersNone
Metabolite Identification
Common NameIsoeugenol
DescriptionIsoeugenol is is a clear to pale yellow oily liquid extracted from certain essential oils especially from clove oil and cinnamon. It is very slightly soluble in water and soluble in organic solvents. It has a spicy odor and taste of clove. Isoeugenol is prepared from eugenol by heating. Eugenol is used in perfumeries, flavorings, essential oils and in medicine (local antiseptic and analgesic). It is used in the production of isoeugenol for the manufacture of vanillin. Eugenol derivatives or methoxyphenol derivatives in wider classification are used in perfumery and flavoring. They are used in formulating insect attractants and UV absorbers, analgesics, biocides and antiseptics. They are also used in manufacturing stabilizers and antioxidants for plastics and rubbers. Isoeugenol is used in manufacturing perfumeries, flavorings, essential oils (odor description: Clove, spicy, sweet, woody) and in medicine (local antiseptic and analgesic) as well as vanillin. (PMID: 15964168 ).
Structure
Thumb
Synonyms
ValueSource
iso-Eugenol 2ChEBI
Isoeugenol (I)ChEBI
Isoeugenol eChEBI
Isoeugenol trans-formChEBI
Isoeugenol ZChEBI
trans-2-Methoxy-4-(1-propenyl)phenolChEBI
trans-2-Methoxy-4-propenylphenolChEBI
trans-P-PropenylquaiacolChEBI
(e)-2-Methoxy-4- (1-propenyl)-phenolHMDB
(e)-2-Methoxy-4-(1-propenyl)-phenolHMDB
(e)-2-Methoxy-4-(prop-1-enyl)phenolHMDB
(e)-2-Methoxy-4-propenyl-phenolHMDB
(e)-IsoeugenolHMDB
1-(3-Methoxy-4-hydroxyphenyl)-1-propaneHMDB
1-Hydroxy-2-methoxy-4-propen-1-ylbenzeneHMDB
2-Methoxy-4-(1-propenyl)-phenolHMDB
2-Methoxy-4-(1-propenyl)phenolHMDB
2-Methoxy-4-(1-propenyl)phenol (acd/name 4.0)HMDB
2-Methoxy-4-propenyl-phenolHMDB
2-Methoxy-4-propenylphenolHMDB
2-Methoxy-4-[(1E)-1-propenyl]phenolHMDB
2-Methoxy-4-[(1E)-prop-1-en-1-yl]phenolHMDB
3-Methoxy-4-hydroxy-1-propen-1-ylbenzeneHMDB
3-Methoxy-4-hydroxypropenylbenzeneHMDB
4-Hydroxy-3-methoxy-1-propen-1-ylbenzeneHMDB
4-Hydroxy-3-methoxy-1-propenylbenzeneHMDB
4-Hydroxy-3-methoxypropenylbenzeneHMDB
PropenylgualacolHMDB
trans-4-PropenylgualacolHMDB
trans-IsoeugenolHMDB
Chemical FormulaC10H12O2
Average Molecular Weight164.2011
Monoisotopic Molecular Weight164.083729628
IUPAC Name2-methoxy-4-[(1E)-prop-1-en-1-yl]phenol
Traditional Nameisoeugenol
CAS Registry Number97-54-1
SMILES
COC1=CC(\C=C\C)=CC=C1O
InChI Identifier
InChI=1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3-7,11H,1-2H3/b4-3+
InChI KeyInChIKey=BJIOGJUNALELMI-ONEGZZNKSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as methoxyphenols. These are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenols and derivatives
Direct ParentMethoxyphenols
Alternative Parents
Substituents
  • Methoxyphenol
  • Phenylpropene
  • Methoxybenzene
  • Styrene
  • Phenol ether
  • Anisole
  • Alkyl aryl ether
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Cosmetic
  • Drug
BiofunctionNot Available
Application
  • Scent and flavoring agent
  • Used in manufacture of vanillin
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-10 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP3.04GRIFFIN,S ET AL. (1999)
Predicted Properties
PropertyValueSource
Water Solubility1.36 mg/mLALOGPS
logP2.79ALOGPS
logP2.64ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)10.01ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity49.86 m3·mol-1ChemAxon
Polarizability18.3 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-0ik9-7900000000-d378eaa3d6e1b33ea92eView in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Saliva
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB002728
KNApSAcK IDC00000620
Chemspider ID21106129
KEGG Compound IDC10469
BioCyc IDISOEUGENOL
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB05802
Metagene LinkHMDB05802
METLIN IDNot Available
PubChem Compound853433
PDB IDEUG
ChEBI ID50545
References
Synthesis ReferenceMannich, C.; Schmitt, Frida. Synthesis of amino alcohols from isosafrole, isoeugenol and anethole. Arch. Pharm. (1928), 266 73-84. CAN 22:39242 AN 1928:39242
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Atsumi T, Fujisawa S, Tonosaki K: A comparative study of the antioxidant/prooxidant activities of eugenol and isoeugenol with various concentrations and oxidation conditions. Toxicol In Vitro. 2005 Dec;19(8):1025-33. Epub 2005 Jun 17. [15964168 ]