CHEBI:4917 - eugenol

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ChEBI Name eugenol
ChEBI ID CHEBI:4917
Definition A phenylpropanoid formally derived from guaiacol with an allyl chain substituted para to the hydroxy group. It is a major component of clove essential oil, and exhibits antibacterial, analgesic and antioxidant properties. It has been widely used in dentistry to treat toothache and pulpitis.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C10H12O2
Net Charge 0
Average Mass 164.204
Monoisotopic Mass 164.08373
InChI InChI=1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3,5-7,11H,1,4H2,2H3
InChIKey RRAFCDWBNXTKKO-UHFFFAOYSA-N
SMILES COC1=CC(CC=C)=CC=C1O
Metabolite of Species Details
Syzygium aromaticum (NCBI:txid219868) See: DOI
Homo sapiens (NCBI:txid9606) Found in blood (UBERON:0000178). See: PubMed
Homo sapiens (NCBI:txid9606) Found in saliva (UBERON:0001836). See: PubMed
Roles Classification
Chemical Role(s): radical scavenger
A role played by a substance that can react readily with, and thereby eliminate, radicals.
Biological Role(s): sensitiser
A chemical compound that causes a substantial proportion of exposed people or animals to develop an allergic reaction in normal tissue after repeated exposure to the compound.
human blood serum metabolite
Any metabolite (endogenous or exogenous) found in human blood serum samples.
allergen
A chemical compound, or part thereof, which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.
volatile oil component
Any plant metabolite that is found naturally as a component of a volatile oil.
flavouring agent
A food additive that is used to added improve the taste or odour of a food.
EC 1.4.3.4 (monoamine oxidase) inhibitor
An EC 1.4.3.* (oxidoreductase acting on donor CH-NH2 group, oxygen as acceptor) inhibitor that interferes with the action of monoamine oxidase (EC 1.4.3.4).
antibacterial agent
A substance (or active part thereof) that kills or slows the growth of bacteria.
apoptosis inducer
Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
analgesic
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.
voltage-gated sodium channel blocker
Any sodium channel blocker that interferes with the activity of voltage-gated sodium channels.
NF-kappaB inhibitor
An inhibitor of NF-kappaB (nuclear factor kappa-light-chain-enhancer of activated B cells), a protein complex involved in the transcription of DNA.
Application(s): flavouring agent
A food additive that is used to added improve the taste or odour of a food.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
anaesthetic
Substance which produces loss of feeling or sensation.
analgesic
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.
anti-inflammatory agent
Any compound that has anti-inflammatory effects.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing eugenol (CHEBI:4917) has functional parent guaiacol (CHEBI:28591)
eugenol (CHEBI:4917) has role allergen (CHEBI:50904)
eugenol (CHEBI:4917) has role anaesthetic (CHEBI:38867)
eugenol (CHEBI:4917) has role analgesic (CHEBI:35480)
eugenol (CHEBI:4917) has role anti-inflammatory agent (CHEBI:67079)
eugenol (CHEBI:4917) has role antibacterial agent (CHEBI:33282)
eugenol (CHEBI:4917) has role antineoplastic agent (CHEBI:35610)
eugenol (CHEBI:4917) has role apoptosis inducer (CHEBI:68495)
eugenol (CHEBI:4917) has role EC 1.4.3.4 (monoamine oxidase) inhibitor (CHEBI:38623)
eugenol (CHEBI:4917) has role flavouring agent (CHEBI:35617)
eugenol (CHEBI:4917) has role human blood serum metabolite (CHEBI:85234)
eugenol (CHEBI:4917) has role NF-κB inhibitor (CHEBI:73240)
eugenol (CHEBI:4917) has role radical scavenger (CHEBI:48578)
eugenol (CHEBI:4917) has role sensitiser (CHEBI:139492)
eugenol (CHEBI:4917) has role volatile oil component (CHEBI:27311)
eugenol (CHEBI:4917) has role voltage-gated sodium channel blocker (CHEBI:38634)
eugenol (CHEBI:4917) is a monomethoxybenzene (CHEBI:25235)
eugenol (CHEBI:4917) is a phenols (CHEBI:33853)
eugenol (CHEBI:4917) is a phenylpropanoid (CHEBI:26004)
Incoming 1'-acetoxyeugenol acetate (CHEBI:470) has functional parent eugenol (CHEBI:4917)
3,5,6-trimethyleugenol (CHEBI:59096) has functional parent eugenol (CHEBI:4917)
3-methyleugenol (CHEBI:59074) has functional parent eugenol (CHEBI:4917)
5-methyleugenol (CHEBI:59072) has functional parent eugenol (CHEBI:4917)
6-methyleugenol (CHEBI:59060) has functional parent eugenol (CHEBI:4917)
O-methyleugenol (CHEBI:4918) has functional parent eugenol (CHEBI:4917)
eugenol sulfate (CHEBI:133570) has functional parent eugenol (CHEBI:4917)
dihydroconiferyl alcohol (CHEBI:4559) is a eugenol (CHEBI:4917)
IUPAC Name
2-methoxy-4-(prop-2-en-1-yl)phenol
Synonyms Sources
1,3,4-Eugenol NIST Chemistry WebBook
1-allyl-3-methoxy-4-hydroxybenzene ChEBI
1-allyl-4-hydroxy-3-methoxybenzene ChEBI
1-Hydroxy-2-methoxy-4-allylbenzene ChemIDplus
1-Hydroxy-2-methoxy-4-prop-2-enylbenzene ChemIDplus
1-Hydroxy-2-methoxy-4-propenylbenzene ChemIDplus
2-Hydroxy-5-allylanisole NIST Chemistry WebBook
2-Methoxy-1-hydroxy-4-allylbenzene ChemIDplus
2-Methoxy-4-(2-propen-1-yl)phenol ChemIDplus
2-méthoxy-4-(2-propèn-1-yl)phénol ChEBI
2-Methoxy-4-(2-propenyl)phenol HMDB
2-Methoxy-4-allylphenol ChemIDplus
2-methoxy-4-prop-2-enyl-phenol PDBeChem
2-Methoxy-4-prop-2-enylphenol ChemIDplus
4-Allyl-1-hydroxy-2-methoxybenzene ChemIDplus
4-Allyl-2-methoxyphenol HMDB
4-allyl-2-methoxyphenol IUPAC
4-Allylcatechol-2-methyl ether NIST Chemistry WebBook
4-Allylguaiacol ChemIDplus
4-Hydroxy-3-methoxy-1-allylbenzene ChemIDplus
Allylguaiacol ChemIDplus
Caryophyllic acid ChemIDplus
Eugenic acid ChemIDplus
eugenol UniProt
Eugenol KEGG COMPOUND
p-Allylguaiacol ChemIDplus
p-Eugenol ChemIDplus
Manual Xrefs Databases
13876103 ChemSpider
2008 BPDB
4648 DrugCentral
C00000619 KNApSAcK
C10453 KEGG COMPOUND
CPD-6481 MetaCyc
D04117 KEGG DRUG
EOL PDBeChem
Eugenol Wikipedia
FDB012171 FooDB
HMDB0005809 HMDB
LSM-2720 LINCS
View more database links
Registry Numbers Types Sources
1366759 Reaxys Registry Number Reaxys
1366759 Beilstein Registry Number Beilstein
97-53-0 CAS Registry Number NIST Chemistry WebBook
97-53-0 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
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Last Modified
08 June 2021