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.
Supplier Information ChemicalBook:CB7208326, eMolecules:500709, ZINC000000001411
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Eugenol is an allyl chain-substituted guaiacol, a member of the allylbenzene class of chemical compounds. It is a colorless to pale yellow, aromatic oily liquid extracted from certain essential oils especially from clove, nutmeg, cinnamon, basil and bay leaf. It is present in concentrations of 80–90% in clove bud oil and at 82–88% in clove leaf oil. Eugenol has a pleasant, spicy, clove-like scent. The name is derived from Eugenia caryophyllata, the former Linnean nomenclature term for cloves. The currently accepted name is Syzygium aromaticum.
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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 alkenylbenzene (CHEBI:195237)
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
97-53-0 CAS Registry Number NIST Chemistry WebBook
97-53-0 CAS Registry Number ChemIDplus
Citations
Ulanowska M, Olas B (2021)
Biological Properties and Prospects for the Application of Eugenol-A Review.
International journal of molecular sciences 22, 3671 [PubMed:33916044]
[show Abstract]
González-Lugo OE, Pozos-Guillén A, Ponce-Peña P, Lares-Asseff I, Escobar-García DM, Campos-Cantón I, Vértiz-Hernández AA (2020)
Synergistic interaction between 4-allyl-1-hydroxy-2-methoxybenzene (eugenol) and diclofenac: An isobolograpic analysis in Wistar rats.
Drug development research 81, 978-984 [PubMed:32737935]
[show Abstract]
Fernandes MJG, Pereira RB, Pereira DM, Fortes AG, Castanheira EMS, Gonçalves MST (2020)
New Eugenol Derivatives with Enhanced Insecticidal Activity.
International journal of molecular sciences 21, E9257 [PubMed:33291666]
[show Abstract]
Gibbs S, Kosten I, Veldhuizen R, Spiekstra S, Corsini E, Roggen E, Rustemeyer T, Feilzer AJ, Kleverlaan CJ (2018)
Assessment of metal sensitizer potency with the reconstructed human epidermis IL-18 assay.
Toxicology 393, 62-72 [PubMed:29079364]
[show Abstract]
Martínez-Herrera A, Pozos-Guillén A, Ruiz-Rodríguez S, Garrocho-Rangel A, Vértiz-Hernández A, Escobar-García DM (2016)
Effect of 4-Allyl-1-hydroxy-2-methoxybenzene (Eugenol) on Inflammatory and Apoptosis Processes in Dental Pulp Fibroblasts.
Mediators of inflammation 2016, 9371403 [PubMed:28044068]
[show Abstract]
Wang C, Fan Y (2014)
Eugenol enhances the resistance of tomato against tomato yellow leaf curl virus.
Journal of the science of food and agriculture 94, 677-682 [PubMed:23852671]
[show Abstract]
Yadav MK, Park SW, Chae SW, Song JJ, Kim HC (2013)
Antimicrobial activities of Eugenia caryophyllata extract and its major chemical constituent eugenol against Streptococcus pneumoniae.
APMIS : acta pathologica, microbiologica, et immunologica Scandinavica 121, 1198-1206 [PubMed:23594212]
[show Abstract]
Narayanan A, Neera, Mallesha, Ramana KV (2013)
Synergized antimicrobial activity of eugenol incorporated polyhydroxybutyrate films against food spoilage microorganisms in conjunction with pediocin.
Applied biochemistry and biotechnology 170, 1379-1388 [PubMed:23666640]
[show Abstract]
Zhang P, Zhang E, Xiao M, Chen C, Xu W (2013)
Enhanced chemical and biological activities of a newly biosynthesized eugenol glycoconjugate, eugenol α-D-glucopyranoside.
Applied microbiology and biotechnology 97, 1043-1050 [PubMed:22923067]
[show Abstract]
Zhang P, Zhang E, Xiao M, Chen C, Xu W (2013)
Study of anti-inflammatory activities of α-D-glucosylated eugenol.
Archives of pharmacal research 36, 109-115 [PubMed:23325490]
[show Abstract]
Devi KP, Sakthivel R, Nisha SA, Suganthy N, Pandian SK (2013)
Eugenol alters the integrity of cell membrane and acts against the nosocomial pathogen Proteus mirabilis.
Archives of pharmacal research 36, 282-292 [PubMed:23444040]
[show Abstract]
Koeduka T, Suzuki S, Iijima Y, Ohnishi T, Suzuki H, Watanabe B, Shibata D, Umezawa T, Pichersky E, Hiratake J (2013)
Enhancement of production of eugenol and its glycosides in transgenic aspen plants via genetic engineering.
Biochemical and biophysical research communications 436, 73-78 [PubMed:23707945]
[show Abstract]
Zhou L, Zheng H, Tang Y, Yu W, Gong Q (2013)
Eugenol inhibits quorum sensing at sub-inhibitory concentrations.
Biotechnology letters 35, 631-637 [PubMed:23264268]
[show Abstract]
Woranuch S, Yoksan R (2013)
Eugenol-loaded chitosan nanoparticles: I. Thermal stability improvement of eugenol through encapsulation.
Carbohydrate polymers 96, 578-585 [PubMed:23768603]
[show Abstract]
Woranuch S, Yoksan R (2013)
Eugenol-loaded chitosan nanoparticles: II. Application in bio-based plastics for active packaging.
Carbohydrate polymers 96, 586-592 [PubMed:23768604]
[show Abstract]
Koch T, Peutzfeldt A, Malinovskii V, Flury S, Häner R, Lussi A (2013)
Temporary zinc oxide-eugenol cement: eugenol quantity in dentin and bond strength of resin composite.
European journal of oral sciences 121, 363-369 [PubMed:23841789]
[show Abstract]
Xu JS, Li Y, Cao X, Cui Y (2013)
The effect of eugenol on the cariogenic properties of Streptococcus mutans and dental caries development in rats.
Experimental and therapeutic medicine 5, 1667-1670 [PubMed:23837051]
[show Abstract]
Nam H, Kim MM (2013)
Eugenol with antioxidant activity inhibits MMP-9 related to metastasis in human fibrosarcoma cells.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 55, 106-112 [PubMed:23313798]
[show Abstract]
Koh T, Murakami Y, Tanaka S, Machino M, Onuma H, Kaneko M, Sugimoto M, Soga T, Tomita M, Sakagami H (2013)
Changes of metabolic profiles in an oral squamous cell carcinoma cell line induced by eugenol.
In vivo (Athens, Greece) 27, 233-243 [PubMed:23422484]
[show Abstract]
Koh T, Murakami Y, Tanaka S, Machino M, Sakagami H (2013)
Re-evaluation of anti-inflammatory potential of eugenol in IL-1β-stimulated gingival fibroblast and pulp cells.
In vivo (Athens, Greece) 27, 269-273 [PubMed:23422489]
[show Abstract]
Shah B, Davidson PM, Zhong Q (2013)
Nanodispersed eugenol has improved antimicrobial activity against Escherichia coli O157:H7 and Listeria monocytogenes in bovine milk.
International journal of food microbiology 161, 53-59 [PubMed:23261812]
[show Abstract]
de Oliveira Pereira F, Mendes JM, de Oliveira Lima E (2013)
Investigation on mechanism of antifungal activity of eugenol against Trichophyton rubrum.
Medical mycology 51, 507-513 [PubMed:23181601]
[show Abstract]
Klein AH, Carstens MI, Carstens E (2013)
Eugenol and carvacrol induce temporally desensitizing patterns of oral irritation and enhance innocuous warmth and noxious heat sensation on the tongue.
Pain 154, 2078-2087 [PubMed:23791894]
[show Abstract]
Rastogi S, Kumar R, Chanotiya CS, Shanker K, Gupta MM, Nagegowda DA, Shasany AK (2013)
4-coumarate: CoA ligase partitions metabolites for eugenol biosynthesis.
Plant & cell physiology 54, 1238-1252 [PubMed:23677922]
[show Abstract]
Spinelli S, Lagarde A, Iovinella I, Legrand P, Tegoni M, Pelosi P, Cambillau C (2012)
Crystal structure of Apis mellifera OBP14, a C-minus odorant-binding protein, and its complexes with odorant molecules.
Insect biochemistry and molecular biology 42, 41-50 [PubMed:22075131]
[show Abstract]
Soini HA, Klouckova I, Wiesler D, Oberzaucher E, Grammer K, Dixon SJ, Xu Y, Brereton RG, Penn DJ, Novotny MV (2010)
Analysis of volatile organic compounds in human saliva by a static sorptive extraction method and gas chromatography-mass spectrometry.
Journal of chemical ecology 36, 1035-1042 [PubMed:20809147]
[show Abstract]
Chung G, Rhee JN, Jung SJ, Kim JS, Oh SB (2008)
Modulation of CaV2.3 calcium channel currents by eugenol.
Journal of dental research 87, 137-141 [PubMed:18218839]
[show Abstract]
Ghosh R, Nadiminty N, Fitzpatrick JE, Alworth WL, Slaga TJ, Kumar AP (2005)
Eugenol causes melanoma growth suppression through inhibition of E2F1 transcriptional activity.
The Journal of biological chemistry 280, 5812-5819 [PubMed:15574415]
[show Abstract]
Takeyoshi M, Noda S, Yamazaki S, Kakishima H, Yamasaki K, Kimber I (2004)
Assessment of the skin sensitization potency of eugenol and its dimers using a non-radioisotopic modification of the local lymph node assay.
Journal of applied toxicology : JAT 24, 77-81 [PubMed:14745850]
[show Abstract]
Fujisawa S, Okada N, Muraoka E (2001)
Comparative effects of eugenol to bis-eugenol on oral mucous membranes.
Dental materials journal 20, 237-242 [PubMed:11806158]
[show Abstract]
Guironnet G, Dalbiez-Gauthier C, Rousset F, Schmitt D, Péguet-Navarro J (2000)
In vitro human T cell sensitization to haptens by monocyte-derived dendritic cells.
Toxicology in vitro : an international journal published in association with BIBRA 14, 517-522 [PubMed:11033063]
[show Abstract]
Bertrand F, Basketter DA, Roberts DW, Lepoittevin JP (1997)
Skin sensitization to eugenol and isoeugenol in mice: possible metabolic pathways involving ortho-quinone and quinone methide intermediates.
Chemical research in toxicology 10, 335-343 [PubMed:9084914]
[show Abstract]
Naidu KA (1995)
Eugenol--an inhibitor of lipoxygenase-dependent lipid peroxidation.
Prostaglandins, leukotrienes, and essential fatty acids 53, 381-383 [PubMed:8596779]
[show Abstract]
Fischer IU, Dengler HJ (1990)
Sensitive high-performance liquid chromatographic assay for the determination of eugenol in body fluids.
Journal of chromatography 525, 369-377 [PubMed:2329164]
[show Abstract]
Last Modified
24 May 2023