Record Information
Version1.0
Creation date2010-04-08 22:05:30 UTC
Update date2018-01-25 19:29:24 UTC
Primary IDFDB002729
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(Z)-Isoeugenol
Description(z)-isoeugenol, also known as (Z)-2-methoxy-4-propenylphenol or cis-4-propenylguaiacol, is a member of the class of compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety (z)-isoeugenol is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). (z)-isoeugenol is a clove and spicy tasting compound found in cloves, which makes (z)-isoeugenol a potential biomarker for the consumption of this food product.
CAS Number5912-86-7
Structure
Thumb
Synonyms
SynonymSource
(Z)-2-Methoxy-4-propenylphenolChEBI
(Z)-IsoeugenolChEBI
cis-2-Methoxy-4-propenylphenolChEBI
cis-4-PropenylguaiacolChEBI
iso-Eugenol 1ChEBI
Isoeugenol (II)ChEBI
Isoeugenol cis-formChEBI
(Z)-2-Methoxy-4-(prop-1-enyl)phenolbiospider
(Z)-2-methoxy-4-propenylphenolbiospider
(z)-isoeugenolbiospider
2-Methoxy-4-[(1Z)-1-propenyl]phenolbiospider
2-methoxy-4-[(1Z)-prop-1-en-1-yl]phenolbiospider
4-(1-Propenyl)-2-methoxyphenol (cis-isoeugenol)biospider
Cis-isoeugenolbiospider
Isoeugenol (z)biospider
Isoeugenol zbiospider
Phenol, 2-methoxy-4-(1-propenyl)-, (Z)-biospider
Phenol, 2-methoxy-4-propenyl-, (Z)-biospider
Z-Isoeugenolbiospider
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
Polarizability17.92 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC10H12O2
IUPAC name2-methoxy-4-[(1Z)-prop-1-en-1-yl]phenol
InChI IdentifierInChI=1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3-7,11H,1-2H3/b4-3-
InChI KeyBJIOGJUNALELMI-ARJAWSKDSA-N
Isomeric SMILES[H]\C(C)=C(/[H])C1=CC(OC)=C(O)C=C1
Average Molecular Weight164.2011
Monoisotopic Molecular Weight164.083729628
Classification
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
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateliquid
Physical DescriptionNot Available
Mass CompositionC 73.15%; H 7.37%; O 19.49%DFC
Melting Point-10 oC
Boiling PointBp13 133-135°DFC
Experimental Water SolubilityNot Available
Experimental logP3.04GRIFFIN,S ET AL. (1999)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data291 (e 3890) (EtOH)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03ds-0900000000-34ba04ec20bd7a697a76View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-976746f8642ed9cede8fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-2900000000-aeeef853384070786115View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6x-9400000000-28c3454817ba3f918700View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-ba4c51d900ead0baa741View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-b71be30e0aefb9374dd3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0535-4900000000-dc2d63615991af22ecd9View in MoNA
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI ID50543
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDCNH06-V:CNH07-W
EAFUS IDNot Available
Dr. Duke IDCIS-ISOEUGENOL
BIGG IDNot Available
KNApSAcK IDC00035903
HET IDNot Available
Flavornet IDNot Available
GoodScent IDrw1096521
SuperScent IDNot Available
Wikipedia IDIsoeugenol
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
spicy
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
clove
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).