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(E)-Isoeugenol (FDB012403)

Record Information
Version1.0
Creation date2010-04-08 22:10:09 UTC
Update date2019-11-26 03:06:43 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
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
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
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
Ontology
OntologyNo ontology term
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0ik9-7900000000-d378eaa3d6e1b33ea92e2014-09-20View Spectrum
GC-MSIsoeugenol, non-derivatized, GC-MS Spectrumsplash10-03di-5900000000-d5e9036e83fd9c1033b0Spectrum
GC-MSIsoeugenol, non-derivatized, GC-MS Spectrumsplash10-03di-4900000000-f0dd30e91dc041336262Spectrum
GC-MSIsoeugenol, non-derivatized, GC-MS Spectrumsplash10-03di-1900000000-1530d67ee6f2740c4978Spectrum
GC-MSIsoeugenol, non-derivatized, GC-MS Spectrumsplash10-03di-5900000000-d5e9036e83fd9c1033b0Spectrum
GC-MSIsoeugenol, non-derivatized, GC-MS Spectrumsplash10-03di-4900000000-f0dd30e91dc041336262Spectrum
GC-MSIsoeugenol, non-derivatized, GC-MS Spectrumsplash10-03di-1900000000-1530d67ee6f2740c4978Spectrum
Predicted GC-MSIsoeugenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03ds-1900000000-54cb7bf6efac012f1f93Spectrum
Predicted GC-MSIsoeugenol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-7790000000-39afffdef59235ab22a4Spectrum
Predicted GC-MSIsoeugenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - n/a 11V, positivesplash10-0019-0900000000-95d2bb40c1282fcc841b2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 11V, positivesplash10-0a4i-0900000000-66bdcdfc1f3c9d7059ef2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 11V, positivesplash10-0a4i-2900000000-1eef4e3fa8cc372a7bd02020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-000i-0900000000-568dabede3d6d65eef272020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-000i-0900000000-704d8c207b799f62a1652020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-0079-1900000000-dc5eb5b27b41f37fff512020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-00du-6900000000-724fc19b181ae95ed7f02020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 7V, positivesplash10-0006-9400000000-e33fcab9c4877cbfaaa82020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 9V, positivesplash10-00kf-9100000000-7581434dd013744b10fe2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 11V, positivesplash10-014l-9000000000-a332174b204c08062e142020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 14V, positivesplash10-014i-9000000000-eca4e980b9dcfbfa0d882020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-51b1ddd89b75760804fb2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-59e54fb66a534d3ff6dc2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-92bea35f22ee86583e9f2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-976746f8642ed9cede8f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-2900000000-aeeef8533840707861152016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6x-9400000000-28c3454817ba3f9187002016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-ba4c51d900ead0baa7412016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-b71be30e0aefb9374dd32016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0535-4900000000-dc2d63615991af22ecd92016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0159-0900000000-6f75a3780b4d03c3f78f2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00m3-2900000000-f418214add56c19743ea2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00or-9000000000-95268ee51bd407edd9b82021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-8db47caa9667c101bd0f2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03ds-0900000000-c240e3167c4ef90295d02021-09-25View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 22.53 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Spectrum
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
Food Biomarker OntologyNot Available
VMH 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).