Isoeugenol (CHEM003836)

Record Information
Version1.0
Creation Date2014-09-11 05:20:36 UTC
Update Date2026-05-14 19:41:57 UTC
Accession NumberCHEM003836
Identification
Common NameIsoeugenol
ClassSmall Molecule
Description
Isoeugenol is 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 odor and taste of clove. Isoeugenol is prepared from eugenol by heating. Eugenol is used in perfumeries, flavorings, essential oils and in medicine (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 flavoring. They are used in formulating insect attractants and UV absorbers, analgesics, biocides and antiseptics. They are also used in manufacturing stabilizers and antioxidants for plastics and rubbers. Isoeugenol is used in manufacturing perfumeries, flavorings, essential oils (odor description: Clove, spicy, sweet, woody) and in medicine (local antiseptic and analgesic) as well as vanillin. (1).
Contaminant Sources
  • EAFUS Chemicals
  • FooDB Chemicals
  • T3DB toxins
  • Tobacco Smoke Compounds
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Ether
  • Food Toxin
  • Household Toxin
  • Industrial/Workplace Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
  • Plant Toxin
  • Plastic
  • Solvent
Chemical Structure
MOLSDFPDBSMILESInChI
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
2-Methoxy-4-(prop-1-en-1-yl)phenolKegg
(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
(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 Mass164.201 g/mol
Monoisotopic Mass164.084 g/mol
CAS Registry Number97-54-1
IUPAC Name2-methoxy-4-[(1E)-prop-1-en-1-yl]phenol
Traditional Nameisoeugenol
SMILESCOC1=CC(\C=C\C)=CC=C1O
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
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
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceNot Available
Experimental Properties
PropertyValue
Melting Point-10 °C
Boiling PointNot Available
SolubilityNot 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
Spectra
Spectra
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0005802
FooDB IDFDB012403
Phenol Explorer IDNot Available
KNApSAcK IDC00000620
BiGG IDNot Available
BioCyc IDISOEUGENOL
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkIsoeugenol
Chemspider ID21106129
ChEBI ID50545
PubChem Compound ID853433
Kegg Compound IDC10469
YMDB IDYMDB01677
ECMDB 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
MSDSLink
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=15964168
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=24421258
3. Mannich, C.; Schmitt, Frida. Synthesis of amino alcohols from isosafrole, isoeugenol and anethole. Arch. Pharm. (1928), 266 73-84. CAN 22:39242 AN 1928:39242
4. 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.