ContaminantDB: Isoeugenol

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (4)XML

Record Information

Version

1.0

Creation Date

2014-09-11 05:20:36 UTC

Update Date

2026-03-31 22:18:10 UTC

Accession Number

CHEM003836

Identification

Common Name

Isoeugenol

Class

Small 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(e)-2-Methoxy-4-(prop-1-enyl)phenol	ChEBI
2-Methoxy-4-[(1E)-1-propenyl]phenol	ChEBI
2-Methoxy-4-propenylphenol	ChEBI
3-Methoxy-4-hydroxy-1-propen-1-ylbenzene	ChEBI
3-Methoxy-4-hydroxypropenylbenzene	ChEBI
4-Hydroxy-3-methoxy-1-propenylbenzene	ChEBI
Iso-eugenol 2	ChEBI
Isoeugenol (I)	ChEBI
Isoeugenol e	ChEBI
Isoeugenol trans-form	ChEBI
Propenylgualacol	ChEBI
trans-2-Methoxy-4-(1-propenyl)phenol	ChEBI
trans-2-Methoxy-4-propenylphenol	ChEBI
trans-4-Propenylgualacol	ChEBI
trans-p-Propenylquaiacol	ChEBI
2-Methoxy-4-(prop-1-en-1-yl)phenol	Kegg
(e)-2-Methoxy-4- (1-propenyl)-phenol	HMDB
(e)-2-Methoxy-4-(1-propenyl)-phenol	HMDB
(e)-2-Methoxy-4-propenyl-phenol	HMDB
(E)-Isoeugenol	HMDB
1-(3-Methoxy-4-hydroxyphenyl)-1-propane	HMDB
1-Hydroxy-2-methoxy-4-propen-1-ylbenzene	HMDB
2-Methoxy-4-(1-propenyl)-phenol	HMDB
2-Methoxy-4-(1-propenyl)phenol	HMDB
2-Methoxy-4-(1-propenyl)phenol (acd/name 4.0)	HMDB
2-Methoxy-4-propenyl-phenol	HMDB
2-Methoxy-4-[(1E)-prop-1-en-1-yl]phenol	HMDB
4-Hydroxy-3-methoxy-1-propen-1-ylbenzene	HMDB
4-Hydroxy-3-methoxypropenylbenzene	HMDB
trans-Isoeugenol	HMDB
Isoeugenol, (e)-isomer	MeSH, HMDB
Isoeugenol	MeSH
(E)-2-Methoxy-4-(1-propenyl)phenol	HMDB
(E)-2-Methoxy-4-(prop-1-en-1-yl)phenol	HMDB
1-(3-Methoxy-4-hydroxyphenyl)-1-propene	HMDB
2-Methoxy-4(E)-1-propenylphenol	HMDB
2-Methoxy-4-(1-propen-1-yl)phenol	HMDB
2-Methoxy-4-(1E)-1-propen-1-ylphenol	HMDB
2-Methoxy-4-[(E)-1-propenyl]phenol	HMDB
3-Methoxy-4-hydroxy-1-propenylbenzene	HMDB
4-(1-Propenyl) Guaiacol	HMDB
4-Hydroxy-3-methoxy-beta-methylstyrene	HMDB
4-Hydroxy-3-methoxy-β-methylstyrene	HMDB
4-Propenylguaiacol	HMDB
iso-Eugenol	HMDB
trans-4-Propenylguaiacol	HMDB
trans-p-Propenylguaiacol	HMDB

Chemical Formula

C₁₀H₁₂O₂

Average Molecular Mass

164.201 g/mol

Monoisotopic Mass

164.084 g/mol

CAS Registry Number

97-54-1

IUPAC Name

2-methoxy-4-[(1E)-prop-1-en-1-yl]phenol

Traditional Name

isoeugenol

SMILES

COC1=CC(\C=C\C)=CC=C1O

InChI Identifier

InChI=1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3-7,11H,1-2H3/b4-3+

InChI Key

BJIOGJUNALELMI-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.

Kingdom

Super Class

Class

Sub Class

Direct Parent

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 Framework

Aromatic homomonocyclic compounds

External Descriptors

isoeugenol (CHEBI:50545 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Liquid

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	-10 °C
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	1.36 g/L	ALOGPS
logP	2.79	ALOGPS
logP	2.64	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	10.01	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.46 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	49.86 m³·mol⁻¹	ChemAxon
Polarizability	18.3 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03di-5900000000-d5e9036e83fd9c1033b0	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03di-4900000000-f0dd30e91dc041336262	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03di-1900000000-1530d67ee6f2740c4978	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03di-5900000000-d5e9036e83fd9c1033b0	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03di-4900000000-f0dd30e91dc041336262	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03di-1900000000-1530d67ee6f2740c4978	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03ds-1900000000-54cb7bf6efac012f1f93	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00di-7790000000-39afffdef59235ab22a4	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 11V, positive	splash10-0019-0900000000-95d2bb40c1282fcc841b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 11V, positive	splash10-0a4i-0900000000-66bdcdfc1f3c9d7059ef	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 11V, positive	splash10-0a4i-2900000000-1eef4e3fa8cc372a7bd0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, positive	splash10-000i-0900000000-568dabede3d6d65eef27	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, positive	splash10-000i-0900000000-704d8c207b799f62a165	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, positive	splash10-0079-1900000000-dc5eb5b27b41f37fff51	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 6V, positive	splash10-00du-6900000000-724fc19b181ae95ed7f0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 7V, positive	splash10-0006-9400000000-e33fcab9c4877cbfaaa8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 9V, positive	splash10-00kf-9100000000-7581434dd013744b10fe	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 11V, positive	splash10-014l-9000000000-a332174b204c08062e14	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 14V, positive	splash10-014i-9000000000-eca4e980b9dcfbfa0d88	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9100000000-51b1ddd89b75760804fb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0900000000-59e54fb66a534d3ff6dc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-92bea35f22ee86583e9f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-976746f8642ed9cede8f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-2900000000-aeeef853384070786115	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f6x-9400000000-28c3454817ba3f918700	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0900000000-ba4c51d900ead0baa741	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0900000000-b71be30e0aefb9374dd3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0535-4900000000-dc2d63615991af22ecd9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0159-0900000000-6f75a3780b4d03c3f78f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00m3-2900000000-f418214add56c19743ea	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00or-9000000000-95268ee51bd407edd9b8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0900000000-8db47caa9667c101bd0f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03ds-0900000000-c240e3167c4ef90295d0	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0ik9-7900000000-d378eaa3d6e1b33ea92e	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0005802

FooDB ID

FDB012403

Phenol Explorer ID

Not Available

KNApSAcK ID

C00000620

BiGG ID

Not Available

BioCyc ID

ISOEUGENOL

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

ECMDB ID

Not Available

References

Synthesis Reference

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

MSDS

Link

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.

Isoeugenol (CHEM003836)

Structure for CHEM003836: Isoeugenol