Record Information
Version1.0
Creation date2010-04-08 22:05:30 UTC
Update date2020-09-17 15:35:23 UTC
Primary IDFDB002728
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameIsoeugenol
DescriptionIsoeugenol is an isomer of eugenol, wherein the double bond on the alkyl chain is shifted by one carbon. It also known as propenylgualacol, 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. Isoeugenol is also classified as a phenylpropene, a propenyl-substituted guaiacol. Isoeugenol may occur as either the cis (Z) or trans (E) isomer. Trans (E) isoeugenol is crystalline while cis (Z) isoeugenol is a pale, yellow liquid. Isoeugenol is very slightly soluble in water and soluble in organic solvents. It has a spicy, sweet, carnation-like odour and tastes of sweet spice and clove. Isoeugenol is a widely used food flavoring agent and a perfuming agent. As a food flavoring agent, it is responsible for the flavor of nutmeg (in pumpkin pies), As a fragrance, it is extensively used as a scent agent in consumer products such as soaps, shampoos, perfumes, detergents and bath tissues (often labeled as “Fragrance” rather than isoeugenol). However, some individuals can develop allergies to isoeugenol as it appears to be a strong contact allergen (PMID: 10554062). Isoeugenol can be prepared from eugenol by heating. In addition to its industrial production via eugenol, isoeugenol can also be extracted from certain essential oils especially from clove oil and cinnamon. It is found naturally in a wide number of foods, spices and plants including allspice, basil, blueberries, cinnamon, cloves, coffee, dill, ginber, nutmeg, thyme and turmeric.
CAS Number97-54-1
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
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
2-Methoxy-4-propenyl phenolbiospider
5-(1-Propenyl)guaiacoldb_source
FEMA 2468db_source
Iso-eugenol 2ChEBI
Phenol, 2-methoxy-4-(1-propen-1-yl)-biospider
Phenol, 2-methoxy-4-(1-propenyl)-biospider
Phenol, 2-methoxy-4-propenyl-biospider
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
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

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 PointNot Available
Experimental Water SolubilityNot Available
Experimental logP3.04GRIFFIN,S ET AL. (1999)
Experimental pKa9.88
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0ik9-7900000000-d378eaa3d6e1b33ea92eSpectrum
EI-MSMass Spectrum (Electron Ionization)splash10-0a4i-9800000000-24fa3ff739ff064312abSpectrum
EI-MSMass Spectrum (Electron Ionization)splash10-0a4i-8900000000-5b42adf83e422cffefb6Spectrum
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
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - n/a 11V, positivesplash10-0019-0900000000-95d2bb40c1282fcc841bSpectrum
MS/MSLC-MS/MS Spectrum - n/a 11V, positivesplash10-0a4i-0900000000-66bdcdfc1f3c9d7059efSpectrum
MS/MSLC-MS/MS Spectrum - n/a 11V, positivesplash10-0a4i-2900000000-1eef4e3fa8cc372a7bd0Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-000i-0900000000-568dabede3d6d65eef27Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-000i-0900000000-704d8c207b799f62a165Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-0079-1900000000-dc5eb5b27b41f37fff51Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-00du-6900000000-724fc19b181ae95ed7f0Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 7V, positivesplash10-0006-9400000000-e33fcab9c4877cbfaaa8Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 9V, positivesplash10-00kf-9100000000-7581434dd013744b10feSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 11V, positivesplash10-014l-9000000000-a332174b204c08062e14Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 14V, positivesplash10-014i-9000000000-eca4e980b9dcfbfa0d88Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-976746f8642ed9cede8fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-2900000000-aeeef853384070786115Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6x-9400000000-28c3454817ba3f918700Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-ba4c51d900ead0baa741Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-b71be30e0aefb9374dd3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0535-4900000000-dc2d63615991af22ecd9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0159-0900000000-6f75a3780b4d03c3f78fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00m3-2900000000-f418214add56c19743eaSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00or-9000000000-95268ee51bd407edd9b8Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
ChemSpider ID21106129
ChEMBL IDCHEMBL193598
KEGG Compound IDC10469
Pubchem Compound ID853433
Pubchem Substance IDNot Available
ChEBI ID18224
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB05802
CRC / DFC (Dictionary of Food Compounds) IDCNH06-V:CNH06-V
EAFUS ID1886
Dr. Duke IDISOEUGENOL
BIGG IDNot Available
KNApSAcK IDC00000620
HET IDEUG
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID97-54-1
GoodScent IDrw1006911
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 / Bioactivities
DescriptorIDDefinitionReference
allergenic50904 A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.DUKE
anti aggregantDUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
anti TNF35222 A substance that diminishes the rate of a chemical reaction.DUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
bacteristat33282 A substance that kills or slows the growth of bacteria.DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
candidistatDUKE
cytotoxic52209 A role played by the molecular entity or part thereof which causes the development of a pathological process.DUKE
fungistatDUKE
motor depressantDUKE
motor stimulantDUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
sedative35717 A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.DUKE
trichomonistatDUKE
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
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.
clove
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
woody
  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.
floral
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
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).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.