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Compound Summary

General Compound Information

eugenol (4-allyl-2-methoxyphenol)

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Description

Eugenol is a phenylpropanoid formally derived from guaiacol with an allyl chain substituted para to the hydroxy group. It has a role as an allergen, a plant metabolite, a human blood serum metabolite and a sensitiser. It is a phenylpropanoid, a monomethoxybenzene and a member of phenols. It derives from a guaiacol.

Synonyms

eugenol; 97-53-0; 4-Allyl-2-methoxyphenol; 4-Allylguaiacol; Eugenic acid;

Allylguaiacol;Caryophyllic acid;p-Allylguaiacol;2-Methoxy-4-prop-2-enylphenol;p-Eugenol;Engenol;2-Methoxy-4-allylphenol;Phenol, 2-methoxy-4-(2-propenyl)-;2-Methoxy-4-(2-propenyl)phenol;1,3,4-Eugenol;4-Allylcatechol-2-methyl ether;1-Hydroxy-2-methoxy-4-allylbenzene;5-Allylguaiacol;Synthetic eugenol;2-Methoxy-1-hydroxy-4-allylbenzene;4-Allyl-1-hydroxy-2-methoxybenzene;1-Hydroxy-2-methoxy-4-prop-2-enylbenzene;2-methoxy-4-(prop-2-en-1-yl)phenol;Eugenol (natural);FEMA No. 2467;4-Hydroxy-3-methoxy-1-allylbenzene;2-Hydroxy-5-allylanisole;bioxeda;4-Allylcatechol 2-methyl ether;4-Hydroxy-3-methoxyallylbenzene;2-Methoxy-4-(2-propen-1-yl)phenol;Phenol, 4-allyl-2-methoxy-;NCI-C50453;1-allyl-4-hydroxy-3-methoxybenzene;1-Allyl-3-methoxy-4-hydroxybenzene;2-Metoksy-4-allilofenol;Caryophillic acid;FA 100;Eugenol [USP];NSC 209525;CHEBI:4917;Phenol, 2-methoxy-4-(2-propen-1-yl)-;NSC-8895;NSC-209525;CHEMBL42710;DTXSID9020617;2-Methoxy-4-(3-propenyl)phenol;3T8H1794QW;Eugenol (USP);NCGC00091449-05;DTXCID90617;Eugenol [USAN];WLN: 1U2R DQ CO1;Caswell No. 456BC;FEMA Number 2467;CAS-97-53-0;38219-15-7;CCRIS 306;HSDB 210;2-Metoksy-4-allilofenol [Polish];SR-05000002043;EINECS 202-589-1;MFCD00008654;EPA Pesticide Chemical Code 102701;BRN 1366759;UNII-3T8H1794QW;AI3-00086;Eugenol,(S);4-allyl-2methoxyphenol;3s0e;EUGENOL [VANDF];EUGENOL [FHFI];EUGENOL [HSDB];EUGENOL [IARC];EUGENOL [INCI];EUGENOL [FCC];EUGENOL [II];EUGENOL [MI];EUGENOL [MART.];Spectrum2_001264;Spectrum3_000646;Spectrum4_001783;Spectrum5_000425;EUGENOL [USP-RS];EUGENOL [WHO-DD];4-allyl-2-methoxy-Phenol;bmse010053;Epitope ID:114091;Eugenol, puriss., 98%;EC 202-589-1;SCHEMBL20361;BSPBio_002251;KBioGR_002327;MLS000028901;BIDD:ER0696;DivK1c_000692;SPECTRUM1500296;SPBio_001228;EUGENOL [EP MONOGRAPH];GTPL2425;ZINC1411;EUGENOL [USP MONOGRAPH];HMS502C14;KBio1_000692;KBio3_001471;Eugenol, ReagentPlus(R), 99%;NSC8895;4-(2-Propenyl)-2-methoxyphenol;Eugenol, natural, >=98%, FG;NINDS_000692;Eugenol, >=98%, FCC, FG;HMS1920O08;HMS2091F09;Pharmakon1600-01500296;HY-N0337;Tox21_111134;Tox21_202040;Tox21_300105;BBL027721;BDBM50164168;CCG-38827;NSC209525;NSC757030;s4706;STL371304;Eugenol, tested according to Ph.Eur.;3-(3-methoxy-4-hydroxyphenyl)propene;AKOS000121354;Tox21_111134_1;CS-7807;DB09086;FS-2702;NSC-757030;SDCCGMLS-0066578.P001;IDI1_000692;Eugenol 1000 microg/mL in Acetonitrile;NCGC00091449-01;NCGC00091449-02;NCGC00091449-03;NCGC00091449-04;NCGC00091449-06;NCGC00091449-07;NCGC00091449-08;NCGC00091449-10;NCGC00253915-01;NCGC00259589-01;AC-34149;Eugenol, Vetec(TM) reagent grade, 98%;SMR000059114;SBI-0051381.P003;Eugenol, PESTANAL(R), analytical standard;A0232;FT-0615974;EN300-16622;D04117;AB00051992_02;A845719;Eugenol, primary pharmaceutical reference standard;Q423357;Eugenol, certified reference material, TraceCERT(R);Q-201105;SR-05000002043-1;SR-05000002043-2;BRD-K32977963-001-01-9;BRD-K32977963-001-03-5;Z56347226;EUGENOL (CONSTITUENT OF HOLY BASIL LEAF) [DSC];Eugenol, European Pharmacopoeia (EP) Reference Standard;F0001-2306;2-methoxy-4-(prop-2-en-1-yl)phenol4-allyl-2-methoxyphenol;EUGENOL (CONSTITUENT OF CINNAMOMUM CASSIA BARK) [DSC];EUGENOL (CONSTITUENT OF CINNAMOMUM VERUM BARK) [DSC];Eugenol, United States Pharmacopeia (USP) Reference Standard;Eugenol, Pharmaceutical Secondary Standard; Certified Reference Material;

FlavorDB ID

2551

PUBCHEM ID

Molecular Weight

164.2 Molecular Formula

C10H12O2

Openeye Can Smiles

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

IUPAC Inchikey

RRAFCDWBNXTKKO-UHFFFAOYSA-N

Network

Similarity

CATEGORY	QUALITY	THRESHOLD	OCCURENCE	REFERENCE
smell	clove-like	4.324e-3 µmol/L		details
smell	clove-like	1.523e-2 µmol/L		details
smell	clove-like	1.096e-2 µmol/L	tomato	details

Toxicity Summary
Link to the Distributed Structure-Searchable Toxicity (DSSTox) Database

Food Additive Safety (OFAS)
EUGENOL is used for FLAVORING AGENT OR ADJUVANT. More food additive safty information please view GRAS report.

EFSA's chemical Hazards Database : OpenFoodTox
This compound is found in OpenFoodTox with the name: Eugenol

Reference point : Defined point on an experimental dose–response relationship for the critical effect. This term is synonymous to Point of departure (USA). Reference points include the lowest or no observed adverse effect level (LOAEL/NOAEL) or benchmark dose lower confidence limit (BDML), used to derive a reference value or Margin of Exposure in human and animal health risk assessment. In the ecological area, these include lethal dose (LD50), effect concentration (EC5/ECx), no (adverse) effect concentration/dose (NOEC/NOAEC/NOAED), no (adverse) effect level (NEL/NOAEL), hazard concentration (HC5/HCx) derived from a Species Sensitivity Distributions (SSD) for the ecosystem (EFSA Scientific Committee,2018). Citation: DOI 10.5281/zenodo.4740174

Output ID	SPECIES	Route	Duration Days	END POINT	QUALIFIER	VALUE	UNIT	EFFECT	Toxicity
1313	Rat	oral: unspecified		LD50	=	1930	mg/kg bw	mortality	systemic
1313	Daphnia magna	Not reported	2	EC50	=	1.9	mg/L	mortality
1313	Rainbow trout	Not reported	4	LC50	=	5.6	mg/L	mortality
1313	Scenedesmus subspicatus	Not reported	3	EC50	=	22	mg/L	biomass
1313	Scenedesmus subspicatus	Not reported	3	EC50	=	41	mg/L	growth
1313	Rabbit	Not reported		NOAEL	=	100	mg/kg bw/day	clinical signs	systemic
1313	Rat	Not reported		NOAEL	=	100	mg/kg bw/day	clinical signs	systemic
1345	Rat	oral: unspecified		LD50	=	1930	mg/kg bw	mortality	systemic
1345	Rat	Not reported		NOEL	=	250	mg/kg bw	development	developmental
1345	Daphnia magna	Not reported	2	EC50	=	1.11	mg/L	not reported
1345	Pseudokirchneriella subcapitata	Not reported	3	EC50	=	10	mg/L	biomass
1345	Rainbow trout	Not reported	4	LC50	>	10	mg/L	mortality
1345	Rabbit	Not reported		NOAEL	=	100	mg/kg bw/day	clinical signs	systemic
1345	Rat	Not reported		NOAEL	=	100	mg/kg bw/day	clinical signs	systemic
2311	Rat	Not reported	730	NOAEL	=	300	mg/kg bw/day	body weight	systemic
145	Rat	Not reported	721	NOAEL	=	300	mg/kg bw/day	body weight	systemic

Reference Value

Reference Value : The estimated maximum dose (on a body mass basis) or the concentration of an agent to which an individual may be exposed over a specified period without appreciable risk. Reference values are established by applying an uncertainty factor to the reference point. Examples of reference values in human health include acceptable daily intake (ADI) for food and feed additives, and pesticides, tolerable upper intake levels (UL) for vitamins and minerals, and tolerable daily intake (TDI) for contaminants and food contact materials. For acute effects and operators, the acute reference dose (ARfD) and the acceptable operator exposure level (AOEL). In animal health and the ecological area, these include safe feed concentrations and the Predicted no effect concentration (PNEC) respectively (EFSA Scientific Committee, 2018). Citation: DOI 10.5281/zenodo.4740174

OUTPUT ID	ASSESSMENT	QUALIFIER	VALUE	UNIT	POPULATION
1313	ADI	=	1	mg/kg bw/day	Consumers
1313	AOEL	=	1	mg/kg bw/day	Workers
1345	ADI	=	1	mg/kg bw/day	Consumers
1345	AOEL	=	1	mg/kg bw/day	Workers
145	ADI	=	2.5	mg/kg bw/day	Consumers
145	MSI/FC	=	3	mg/kg bw/day	Cattle for meat production
145	MSI/FC	=	3	mg/kg bw/day	Cattle for meat production - less than 1 year old
145	MSI/FC	=	3	mg/kg bw/day	Cattle for milk production
145	MSI/FC	=	3	mg/kg bw/day	Chicken for egg production
145	MSI/FC	=	3	mg/kg bw/day	Chicken for meat production
145	MSI/FC	=	3	mg/kg bw/day	Pigs - less than 1 year old
145	MSI/FC	=	3	mg/kg bw/day	Pigs for meat production
145	MSI/FC	=	3	mg/kg bw/day	Pigs for reproduction
145	MSI/FC	=	3	mg/kg bw/day	Turkeys for meat production
2703	MSI/FC	=	100	mg/kg	Chicken for meat production

Genotoxicity

Author	YEAR	OUTPUT ID	Genotoxicity
EFSA	2012	1313	Negative
EFSA	2012	1345	Negative
EFSA AFC	2009	2311	Negative
EFSA FEEDAP	2011	145	Not determined
EFSA FEEDAP	2012	246	Negative
EFSA FEEDAP	2015	2703	No data

EFSA Outputs

Output ID	Title	DOI	Published
145	Scientific Opinion on the safety and efficacy of allylhydroxybenzenes (chemical group 18) when used as flavourings for all animal species	doi:10.2903/j.efsa.2011.2440	02Dec2011
246	Scientific Opinion on safety and efficacy of CRINA Poultry Plus (preparation of benzoic acid and essential oil compounds) as feed additive for chickens for fattening	doi:10.2903/j.efsa.2012.2620	23Mar2012
1313	Conclusion on the peer review of the pesticide risk assessment of the active substance plant oils/clove oil	doi:10.2903/j.efsa.2012.2506	17Jan2012
1345	Conclusion on the peer review of the pesticide risk assessment of the active substance eugenol	doi:10.2903/j.efsa.2012.2914	05Nov2012
2311	Flavouring Group Evaluation 60 (FGE.60): Consideration of eugenol and related hydroxyallylbenzene derivatives evaluated by JECFA (65th meeting) structurally related to ring-substituted phenolic substances evaluated by EFSA in FGE.22 (2006). Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in Contact with Food (AFC)	doi:10.2903/j.efsa.2009.965	12Feb2009
2703	Scientific Opinion on the safety and efficacy of Liderfeed (eugenol) for chickens for fattening	doi:10.2903/j.efsa.2015.4273	11Nov2015

Receptors

Receptor	REFERENCE	EC50 [µM]
OR10G3	details	Activated
OR10G7	details	Activated
OR1A1	details	Activated
OR2J2	details	Activated
OR2W1	details	Activated
OR4Q3	details	Activated
OR5K1	details	Activated

Consensus Spectra

Spectrum Type	Spectrum View	Description	Polarity
Experimental GCMS	view	GCMS	positive
Experimental LCMS	view	LCMS_Positive	positive

Content

Compound Summary

eugenol (4-allyl-2-methoxyphenol)

Description

Synonyms

eugenol; 97-53-0; 4-Allyl-2-methoxyphenol; 4-Allylguaiacol; Eugenic acid;

FlavorDB ID

2551

PUBCHEM ID

3314

Molecular Weight

164.2

Molecular Formula

C10H12O2

Openeye Can Smiles

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

IUPAC Inchikey

RRAFCDWBNXTKKO-UHFFFAOYSA-N

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Content

Compound Summary

eugenol (4-allyl-2-methoxyphenol)

Description

Synonyms

eugenol; 97-53-0; 4-Allyl-2-methoxyphenol; 4-Allylguaiacol; Eugenic acid;

FlavorDB ID

2551

PUBCHEM ID

3314

Molecular Weight

164.2

Molecular Formula

C10H12O2

Openeye Can Smiles

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

IUPAC Inchikey

RRAFCDWBNXTKKO-UHFFFAOYSA-N

Network

Shown in network

Similarity

Show/Hide similarity panel

Reference Details

Reference Details

Reference Details

OpenFoodTox: component Eugenol

Reference Details

Reference Details

Reference Details

Reference Details

Reference Details

Reference Details

Reference Details

GC-MS Spectrum

GC-MS Spectrum