ContaminantDB: Eugenol

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (5)XML

Record Information

Version

1.0

Creation Date

2014-09-11 05:20:33 UTC

Update Date

2016-10-28 10:02:27 UTC

Accession Number

CHEM003835

Identification

Common Name

Eugenol

Class

Small Molecule

Description

Eugenol is an allyl chain-substituted guaiacol, i.e. 2-methoxy-4-(2-propenyl)phenol. Eugenol is a member of the allylbenzene class of chemical compounds. It is a clear to pale yellow oily liquid extracted from certain essential oils especially from clove oil, nutmeg, cinnamon, and bay leaf. It is slightly soluble in water and soluble in organic solvents. It has a pleasant, spicy, clove-like odor. Eugenol is used in perfumeries, flavorings, essential oils and in medicine as a local antiseptic and anaesthetic. It was used in the production of isoeugenol for the manufacture of vanillin, though most vanillin is now produced from petrochemicals or from by-products of paper manufacture (Wikipedia).

Contaminant Sources

Cosmetic Chemicals
EAFUS Chemicals
FooDB Chemicals
HPV EPA Chemicals
IARC Carcinogens Group 3
My Exposome Chemicals
STOFF IDENT Compounds
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
Solvent

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,3,4-Eugenol	ChEBI
1-Allyl-3-methoxy-4-hydroxybenzene	ChEBI
1-Allyl-4-hydroxy-3-methoxybenzene	ChEBI
1-Hydroxy-2-methoxy-4-allylbenzene	ChEBI
1-Hydroxy-2-methoxy-4-prop-2-enylbenzene	ChEBI
1-Hydroxy-2-methoxy-4-propenylbenzene	ChEBI
2-Hydroxy-5-allylanisole	ChEBI
2-Methoxy-1-hydroxy-4-allylbenzene	ChEBI
2-Methoxy-4-(2-propen-1-yl)phenol	ChEBI
2-Methoxy-4-(2-propenyl)phenol	ChEBI
2-Methoxy-4-allylphenol	ChEBI
2-Methoxy-4-prop-2-enyl-phenol	ChEBI
2-Methoxy-4-prop-2-enylphenol	ChEBI
4-Allyl-1-hydroxy-2-methoxybenzene	ChEBI
4-Allyl-2-methoxyphenol	ChEBI
4-Allylcatechol-2-methyl ether	ChEBI
4-Allylguaiacol	ChEBI
4-Hydroxy-3-methoxy-1-allylbenzene	ChEBI
Allylguaiacol	ChEBI
Caryophyllic acid	ChEBI
Eugenic acid	ChEBI
p-Allylguaiacol	ChEBI
p-Eugenol	ChEBI
Caryophyllate	Generator
Eugenate	Generator
2-Methoxy-4-(3-propenyl)phenol	HMDB
2-Methoxy-4-(prop-2-en-1-yl)phenol	HMDB
4-Allyl-2-methoxy-phenol	HMDB
4-Allylcatechol 2-methyl ether	HMDB
4-Hydroxy-3-methoxyallylbenzene	HMDB
5-Allylguaiacol	HMDB
Engenol	HMDB
Eugenol (natural)	HMDB
Synthetic eugenol	HMDB
2-Methoxy-4-(2'-propenyl)phenol	PhytoBank
2-Methoxy-4-(2’-propenyl)phenol	PhytoBank
2-Methoxy-4-[2-allyl]phenol	PhytoBank
3-(3-Methoxy-4-hydroxyphenyl)propene	PhytoBank
3-(4-Hydroxy-3-methoxyphenyl)-1-propene	PhytoBank
4-Allenylguaiacol	PhytoBank

Chemical Formula

C₁₀H₁₂O₂

Average Molecular Mass

164.201 g/mol

Monoisotopic Mass

164.084 g/mol

CAS Registry Number

97-53-0

IUPAC Name

2-methoxy-4-(prop-2-en-1-yl)phenol

Traditional Name

eugenol

SMILES

COC1=C(O)C=CC(CC=C)=C1

InChI Identifier

InChI=1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3,5-7,11H,1,4H2,2H3

InChI Key

RRAFCDWBNXTKKO-UHFFFAOYSA-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
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

phenols (CHEBI:4917 )
phenylpropanoid (CHEBI:4917 )
monomethoxybenzene (CHEBI:4917 )
Monolignols (C10453 )
a monoterpenol (CPD-6481 )
a phenol (CPD-6481 )

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

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	-7.5°C (18.5°F)
Boiling Point	253.2°C (487.8°F)
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	1.44 g/L	ALOGPS
logP	2.66	ALOGPS
logP	2.61	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	9.94	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	3	ChemAxon
Refractivity	48.79 m³·mol⁻¹	ChemAxon
Polarizability	17.9 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)	splash10-0ik9-5900000000-3d3a9e4f250074741003	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03di-2900000000-395df8510f0db4933abe	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03di-6900000000-1afdd3b83f6832b11f70	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03di-4900000000-1d96ae8b031e47e13112	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0ik9-6900000000-def0c646d72c040b58da	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03di-0900000000-dfa64951eb648f5c9df1	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0ik9-5900000000-3d3a9e4f250074741003	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03di-2900000000-395df8510f0db4933abe	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03di-6900000000-1afdd3b83f6832b11f70	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03di-4900000000-1d96ae8b031e47e13112	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0ik9-6900000000-def0c646d72c040b58da	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03di-0900000000-dfa64951eb648f5c9df1	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03ms-1900000000-da27a86009649c155318	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00di-8790000000-0d0c6f0e58d7dc3e5620	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-014i-0900000000-4541582e8f6395e2fa87	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-00di-0900000000-84f950d2fc0742e324d5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0ab9-0900000000-4c037643a10913a70f5e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0a4i-0900000000-83f8f32dfd9b94fb1d24	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0a4i-2900000000-c65a2dab49b8ebb431da	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-001i-0900000000-65a67ccd1df0d2f1796f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-0900000000-83f8f32dfd9b94fb1d24	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0ab9-0900000000-4c037643a10913a70f5e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-4541582e8f6395e2fa87	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0900000000-84f950d2fc0742e324d5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-f5092971e88a27de65e9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-0a4i-2900000000-c65a2dab49b8ebb431da	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-0900000000-7beab8e102e0252d1a87	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-9d2a857e8a482a061127	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-2900000000-9c846765367542bf4db1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fr6-9500000000-98fcaf3ccca850c34bd3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0900000000-835320dc79855273af7f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0900000000-3a70eb9601589d9108a1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052e-4900000000-1c4834945c53d64bab3b	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	splash10-03ka-0900000000-ab5855c31f23e61c7f54	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03k9-3900000000-868b72d9162a6b307829	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0159-0900000000-63a94aabae02f360ee77	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05nr-1900000000-ce4d363c5e701cb34dfd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-9000000000-8e444a7d43baeb4d68f0	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0il0-6900000000-ff0dc492bab70317bb2a	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)

3, not classifiable as to its carcinogenicity to humans. (1)

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

HMDB ID

FooDB ID

Phenol Explorer ID

KNApSAcK ID

BiGG ID

Not Available

BioCyc ID

METLIN ID

PDB ID

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

ECMDB ID

Not Available

References

Synthesis Reference

Ogiso, Akira; Kobayashi, Shinsaku. a-Vinylbenzylalcohol derivatives. Jpn. Kokai Tokkyo Koho (1974), 6 pp. CODEN: JKXXAF JP 49036644 19740405 Showa. CAN 82:16534 AN 1975:16534

MSDS

Link

General References

1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11033063

2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11806158

3. https://www.ncbi.nlm.nih.gov/pubmed/?term=14745850

4. https://www.ncbi.nlm.nih.gov/pubmed/?term=15574415

5. https://www.ncbi.nlm.nih.gov/pubmed/?term=18218839

6. https://www.ncbi.nlm.nih.gov/pubmed/?term=20809147

7. https://www.ncbi.nlm.nih.gov/pubmed/?term=22075131

8. https://www.ncbi.nlm.nih.gov/pubmed/?term=22923067

9. https://www.ncbi.nlm.nih.gov/pubmed/?term=23181601