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Showing metabocard for Isoeugenol (HMDB0005802)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2007-01-22 22:53:28 UTC
Update Date2020-06-15 17:04:52 UTC
HMDB IDHMDB0005802
Secondary Accession Numbers
  • HMDB05802
Metabolite Identification
Common NameIsoeugenol
DescriptionIsoeugenol (CAS: 97-54-1) 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 odour and tastes of clove. Isoeugenol is prepared from eugenol by heating. Eugenol is used in perfumeries, flavourings, essential oils, and medicine (i.e. 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 flavouring. They are used in formulating insect attractants, UV absorbers, analgesics, biocides, and antiseptics. They are also used in manufacturing stabilizers and antioxidants for plastics and rubbers (PMID: 15964168 ).
Structure
Data?1586373874
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(e)-2-Methoxy-4-(prop-1-enyl)phenolChEBI
2-Methoxy-4-[(1E)-1-propenyl]phenolChEBI
2-Methoxy-4-propenylphenolChEBI
3-Methoxy-4-hydroxy-1-propen-1-ylbenzeneChEBI
3-Methoxy-4-hydroxypropenylbenzeneChEBI
4-Hydroxy-3-methoxy-1-propenylbenzeneChEBI
iso-Eugenol 2ChEBI
Isoeugenol (I)ChEBI
Isoeugenol eChEBI
Isoeugenol trans-formChEBI
PropenylgualacolChEBI
trans-2-Methoxy-4-(1-propenyl)phenolChEBI
trans-2-Methoxy-4-propenylphenolChEBI
trans-4-PropenylgualacolChEBI
trans-P-PropenylquaiacolChEBI
(e)-2-Methoxy-4- (1-propenyl)-phenolHMDB
(e)-2-Methoxy-4-(1-propenyl)-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-[(1E)-prop-1-en-1-yl]phenolHMDB
4-Hydroxy-3-methoxy-1-propen-1-ylbenzeneHMDB
4-Hydroxy-3-methoxypropenylbenzeneHMDB
trans-IsoeugenolHMDB
Isoeugenol, (e)-isomerMeSH, HMDB
IsoeugenolMeSH
2-Methoxy-4-(prop-1-en-1-yl)phenolKEGG
(E)-2-Methoxy-4-(1-propenyl)phenolHMDB
(E)-2-Methoxy-4-(prop-1-en-1-yl)phenolHMDB
1-(3-Methoxy-4-hydroxyphenyl)-1-propeneHMDB
2-Methoxy-4(E)-1-propenylphenolHMDB
2-Methoxy-4-(1-propen-1-yl)phenolHMDB
2-Methoxy-4-(1E)-1-propen-1-ylphenolHMDB
2-Methoxy-4-[(E)-1-propenyl]phenolHMDB
3-Methoxy-4-hydroxy-1-propenylbenzeneHMDB
4-(1-Propenyl) GuaiacolHMDB
4-Hydroxy-3-methoxy-beta-methylstyreneHMDB
4-Hydroxy-3-methoxy-β-methylstyreneHMDB
4-PropenylguaiacolHMDB
iso-EugenolHMDB
trans-4-PropenylguaiacolHMDB
trans-p-PropenylguaiacolHMDB
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 Number5932-68-3
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 KeyBJIOGJUNALELMI-ONEGZZNKSA-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
  • Styrene
  • 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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity49.86 m³·mol⁻¹ChemAxon
Polarizability18.3 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-5900000000-d5e9036e83fd9c1033b0Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-4900000000-f0dd30e91dc041336262Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-1900000000-1530d67ee6f2740c4978Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-5900000000-d5e9036e83fd9c1033b0Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-4900000000-f0dd30e91dc041336262Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-1900000000-1530d67ee6f2740c4978Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03ds-1900000000-54cb7bf6efac012f1f93Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-7790000000-39afffdef59235ab22a4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-976746f8642ed9cede8fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-2900000000-aeeef853384070786115Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6x-9400000000-28c3454817ba3f918700Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-ba4c51d900ead0baa741Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-b71be30e0aefb9374dd3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0535-4900000000-dc2d63615991af22ecd9Spectrum
MSMass Spectrum (Electron Ionization)splash10-0ik9-7900000000-d378eaa3d6e1b33ea92eSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not Quantified Adult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012403
KNApSAcK IDC00000620
Chemspider ID21106129
KEGG Compound IDC10469
BioCyc IDISOEUGENOL
BiGG IDNot Available
Wikipedia LinkIsoeugenol
METLIN IDNot Available
PubChem Compound853433
PDB IDNot Available
ChEBI ID50545
Food Biomarker OntologyNot Available
VMH IDNot Available
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. [PubMed:15964168 ]