Canmetcon
Record Information
Version1.0
Creation date2010-04-08 22:10:09 UTC
Update date2018-05-29 00:57:58 UTC
Primary IDFDB012403
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(E)-Isoeugenol
Description(e)-isoeugenol, also known as 2-methoxy-4-propenylphenol or propenylgualacol, 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 (e)-isoeugenol is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). (e)-isoeugenol is a sweet, carnation, and clove tasting compound and can be found in a number of food items such as corn salad, coconut, flaxseed, and winter squash, which makes (e)-isoeugenol a potential biomarker for the consumption of these food products (e)-isoeugenol can be found primarily in saliva (e)-isoeugenol exists in all eukaryotes, ranging from yeast to humans (e)-isoeugenol is a non-carcinogenic (not listed by IARC) potentially toxic compound.
CAS Number5932-68-3
Structure
Thumb
Synonyms
SynonymSource
(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
Isoeugenol ZChEBI
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, sodium saltHMDB
Isoeugenol, (e)-isomerHMDB
Isoeugenol, (Z)-isomerHMDB
IsoeugenolMeSH
(E)-2-Methoxy-4-(prop-1-enyl)phenolbiospider
(e)-isoeugenolbiospider
2-methoxy-4-[(1E)-prop-1-en-1-yl]phenolbiospider
E-4-propenyl-2-methoxyphenolbiospider
E-Isoeugenolbiospider
Phenol, 2-methoxy-4-(1-propenyl)-, (E)-biospider
Phenol, 2-methoxy-4-(1-propenyl)-, (E)- (9CI)biospider
Phenol, 2-methoxy-4-propenyl-, (E)-biospider
trans-2-methoxy-4-(1-propenyl)phenolbiospider
Trans-isoeugenolbiospider
Trans-p-propenylquaiacolbiospider
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC10H12O2
IUPAC name2-methoxy-4-[(1E)-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-ONEGZZNKSA-N
Isomeric SMILESCOC1=CC(\C=C\C)=CC=C1O
Average Molecular Weight164.2011
Monoisotopic Molecular Weight164.083729628
Classification
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
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 73.15%; H 7.37%; O 19.49%DFC
Melting PointMp 33°DFC
Boiling PointBp12 140-141°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKapKa 9.88 (25°)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data[neutral] lmax 260 (e 15135) (EtOH)DFC
DensityNot Available
Refractive Indexn20D 1.5790DFC
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-5900000000-d5e9036e83fd9c1033b0View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-4900000000-f0dd30e91dc041336262View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-1900000000-1530d67ee6f2740c4978View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-5900000000-d5e9036e83fd9c1033b0View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-4900000000-f0dd30e91dc041336262View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-1900000000-1530d67ee6f2740c4978View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03ds-1900000000-54cb7bf6efac012f1f93View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-7790000000-39afffdef59235ab22a4View 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
MSMass Spectrum (Electron Ionization)splash10-0ik9-7900000000-d378eaa3d6e1b33ea92eView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID853433
Pubchem Substance IDNot Available
ChEBI ID50545
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDCNH06-V:HGS84-A
EAFUS IDNot Available
Dr. Duke IDTRANS-ISOEUGENOL
BIGG IDNot Available
KNApSAcK IDC00035095
HET IDNot Available
Flavornet ID5932-68-3
GoodScent IDrw1060831
SuperScent ID853433
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
flower
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
clove
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
sweet
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
spicy
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
carnation
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
phenolic
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
floral
  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).