AFCDB: Eugenol (FDB012171)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:02 UTC

Update date

2020-09-17 15:30:01 UTC

Primary ID

FDB012171

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Eugenol

Description

Eugenol or 4-allyl-2-methoxyphenol is classified as a phenylpropanoid, formally derived from guaiacol, with an allyl chain substituted para to the hydroxy group. It is soluble in water, alcohol, chloroform, ether and oils. Eugenol is a neutral compound. It is biosynthesized from tyrosine. Eugenol exists in all eukaryotes, from yeast to humans. It is a clear to pale yellow oily liquid extracted from clove oil, nutmeg, cinnamon, basil and bay leaf. It has a pleasant, spicy, clove-like odor with a spicy pungent taste. Eugenol is found in highest concentrations in cloves, allspices, and carrots and in lower concentrations in walnuts, ceylon cinnamons, and wild carrots. Eugenol has also been detected in shea tree, passion fruits, winged beans, fireweeds, and gingers, making it a potential biomarker for the consumption of these foods. It is a noncannabinoid phenol compound found in cannabis plants (PMID: 6991645). Eugenol is used in perfumeries, flavorings and essential oils. It was first used for the manufacture of vanillin (https://doi.org/10.1021/ed054p776), though most vanillin is now produced from petrochemicals or from by-products of paper manufacture. Eugenol is hepatotoxic, meaning it may cause damage to the liver, if consumed in high doses. Eugenol has local antiseptic and anaesthetic properties (PMID: 15089054; PMID: 935250) and acts as positive allosteric modulators of the GABAA receptor. It has high antioxidant, anti-proliferative, and anti-inflammatory activities with potential roles in alleviating and preventing cancer and inflammatory reactions (PMID: 27771920).

CAS Number

97-53-0

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C10H12O2

IUPAC name

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

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

Isomeric SMILES

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

Average Molecular Weight

164.2011

Monoisotopic Molecular Weight

164.083729628

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.

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 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Synthetic:

Personal care product

Environmental:

Tobacco smoke

Biological:

Animal

Plant:

Biological location:

Subcellular:

Biofluid and excreta:

Role

Environmental role:

Environmental contaminant

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 73.15%; H 7.37%; O 19.49%	DFC
Melting Point	Fp -9°	DFC
Boiling Point	Bp15 128-130°	DFC
Experimental Water Solubility	2.46 mg/mL at 25 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP	2.27	SANGSTER (1993)
Experimental pKa	pKa1 10.19 (25°)	DFC
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	d204 1.07	DFC
Refractive Index	n20D 1.5400	DFC

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0il0-6900000000-ff0dc492bab70317bb2a	2014-09-20	View Spectrum
GC-MS	Eugenol, non-derivatized, GC-MS Spectrum	splash10-0ik9-5900000000-3d3a9e4f250074741003	Spectrum
GC-MS	Eugenol, non-derivatized, GC-MS Spectrum	splash10-03di-2900000000-395df8510f0db4933abe	Spectrum
GC-MS	Eugenol, non-derivatized, GC-MS Spectrum	splash10-03di-6900000000-1afdd3b83f6832b11f70	Spectrum
GC-MS	Eugenol, non-derivatized, GC-MS Spectrum	splash10-03di-4900000000-1d96ae8b031e47e13112	Spectrum
GC-MS	Eugenol, non-derivatized, GC-MS Spectrum	splash10-0ik9-6900000000-def0c646d72c040b58da	Spectrum
GC-MS	Eugenol, non-derivatized, GC-MS Spectrum	splash10-03di-0900000000-dfa64951eb648f5c9df1	Spectrum
GC-MS	Eugenol, non-derivatized, GC-MS Spectrum	splash10-0ik9-5900000000-3d3a9e4f250074741003	Spectrum
GC-MS	Eugenol, non-derivatized, GC-MS Spectrum	splash10-03di-2900000000-395df8510f0db4933abe	Spectrum
GC-MS	Eugenol, non-derivatized, GC-MS Spectrum	splash10-03di-6900000000-1afdd3b83f6832b11f70	Spectrum
GC-MS	Eugenol, non-derivatized, GC-MS Spectrum	splash10-03di-4900000000-1d96ae8b031e47e13112	Spectrum
GC-MS	Eugenol, non-derivatized, GC-MS Spectrum	splash10-0ik9-6900000000-def0c646d72c040b58da	Spectrum
GC-MS	Eugenol, non-derivatized, GC-MS Spectrum	splash10-03di-0900000000-dfa64951eb648f5c9df1	Spectrum
Predicted GC-MS	Eugenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-03ms-1900000000-da27a86009649c155318	Spectrum
Predicted GC-MS	Eugenol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-8790000000-0d0c6f0e58d7dc3e5620	Spectrum
Predicted GC-MS	Eugenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Eugenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-014i-0900000000-4541582e8f6395e2fa87	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-00di-0900000000-84f950d2fc0742e324d5	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0ab9-0900000000-4c037643a10913a70f5e	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0a4i-0900000000-83f8f32dfd9b94fb1d24	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0a4i-2900000000-c65a2dab49b8ebb431da	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-001i-0900000000-65a67ccd1df0d2f1796f	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-0900000000-83f8f32dfd9b94fb1d24	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0ab9-0900000000-4c037643a10913a70f5e	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-4541582e8f6395e2fa87	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0900000000-84f950d2fc0742e324d5	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-f5092971e88a27de65e9	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-0a4i-2900000000-c65a2dab49b8ebb431da	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-0900000000-7beab8e102e0252d1a87	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-9d2a857e8a482a061127	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-2900000000-9c846765367542bf4db1	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fr6-9500000000-98fcaf3ccca850c34bd3	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0900000000-835320dc79855273af7f	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0900000000-3a70eb9601589d9108a1	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052e-4900000000-1c4834945c53d64bab3b	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0900000000-8db47caa9667c101bd0f	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03ka-0900000000-ab5855c31f23e61c7f54	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03k9-3900000000-868b72d9162a6b307829	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0159-0900000000-63a94aabae02f360ee77	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05nr-1900000000-ce4d363c5e701cb34dfd	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-9000000000-8e444a7d43baeb4d68f0	2021-09-22	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 15.09 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

470

Phenol-Explorer ID

646

DrugBank ID

Not Available

HMDB ID

HMDB05809

CRC / DFC (Dictionary of Food Compounds) ID

HDW90-Y:HDW90-Y

EAFUS ID

1326

Dr. Duke ID

EUGENOL

BIGG ID

Not Available

KNApSAcK ID

C00000619

HET ID

EOL

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

GoodScent ID

SuperScent ID

Wikipedia ID

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
acaricide	22153	A substance used to destroy pests of the subclass Acari (mites and ticks).	DUKE
allergenic	50904	A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.	DUKE
analgesic	35480	An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.	DUKE
anesthetic			DUKE
anti aggregant			DUKE
anti arachidonate	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
anti bacterial	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti convulsant	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti edemic			DUKE
anti estrogenic	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
anti feedant			DUKE
anti genotoxic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti herpetic	22587	A substance that destroys or inhibits replication of viruses.	DUKE
anti inflammatory	35472	A substance that reduces or suppresses inflammation.	DUKE
anti keratotic			DUKE
anti mitotic			DUKE
anti mutagenic			DUKE
anti nitrosating			DUKE
antioxidant	22586	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 prostaglandin	49020	A chemical substance which inhibits the function of the endocrine glands, the biosynthesis of their secreted hormones, or the action of hormones upon their specific sites.	DUKE
anti pyretic	35493	A drug that prevents or reduces fever by lowering the body temperature from a raised state. An antipyretic will not affect the normal body temperature if one does not have fever. Antipyretics cause the hypothalamus to override an interleukin-induced increase in temperature. The body will then work to lower the temperature and the result is a reduction in fever.	DUKE
anti radicular			DUKE
anti salmonella	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti septic	33281	A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.	DUKE
anti spasmodic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti staphylococcic	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti thromboxane	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
anti TNF	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
antitumor	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti ulcer	49201	One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.	DUKE
anti viral	22587	A substance that destroys or inhibits replication of viruses.	DUKE
apifuge	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE
calcium antagonist	48706	Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances.	DUKE
cancer preventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
candidicide			DUKE
carcinogenic	50903	A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.	DUKE
carminative			DUKE
choleretic			DUKE
central nervous system depressant	35470	A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.	DUKE
cyclooxygenase-1 inhibitor	50630	A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 1.	DUKE
cyclooxygenase-2 inhibitor	50629	A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.	DUKE
cytochrome-P450 inhibitor	50183	An enzyme inhibitor that interferes with the activity of cytochrome P450 involved in catalysis of organic substances.	DUKE
cytotoxic	52209	A role played by the molecular entity or part thereof which causes the development of a pathological process.	DUKE
dermatitigenic			DUKE
enterorelaxant			DUKE
flavor	48318	A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.	DUKE
fungicide	24127	A substance used to destroy fungal pests.	DUKE
hepatoprotective	62868	Any compound that is able to prevent damage to the liver.	DUKE
herbicide	24527	A substance used to destroy plant pests.	DUKE
insecticide	24852	Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.	DUKE
insectifuge	24852	Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.	DUKE
irritant			DUKE
juvabional			DUKE
larvicide			DUKE
motor depressant			DUKE
nematicide	25491	A substance used to destroy pests of the phylum Nematoda (roundworms).	DUKE
neurotoxic	50910	A poison that interferes with the functions of the nervous system.	DUKE
perfumery	48318	A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.	DUKE
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE
prostaglandin synthesis inhibitor	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
sedative	35717	A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.	DUKE
termiticide			DUKE
trichomonicide			DUKE
trichomonistat			DUKE
trypsin enhancer			DUKE
ulcerogenic			DUKE
varroacide			DUKE
vasodilator	35620	A drug used to cause dilation of the blood vessels.	DUKE
vermifuge	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE

Enzymes

Name	Gene Name	UniProt ID
UDP-glucuronosyltransferase 2B28	UGT2B28	Q9BY64
UDP-glucuronosyltransferase 2B17	UGT2B17	O75795

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
clove	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 Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695 The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
honey	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
cinnamon	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
sweet	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
spicy	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
woody	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.

Eugenol (FDB012171)

Structure for FDB012171 (Eugenol)