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Details

Stereochemistry ACHIRAL
Molecular Formula C10H12O2
Molecular Weight 164.2011
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of EUGENOL

SMILES

COC1=CC(CC=C)=CC=C1O

InChI

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

HIDE SMILES / InChI

Molecular Formula C10H12O2
Molecular Weight 164.2011
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including: https://www.drugs.com/otc/470846/eugenol-toothache-medication.html | http://www.indepthinfo.com/nutrition/eugenol.htm

Eugenol is sometimes called clove oil because it is the active element in cloves. It causes the aromatic smell typical of cloves and because of this property is often found in perfumes. Eugenol’s properties make it a good local antiseptic and analgesic. It is used in dentist offices to make zinc-oxide eugenol paste for temporary fillings. Eugenol also demonstrates antifungal and antimicrobial activity, showing efficacy against Candida albicans biofilms, Listeria monocytogenes and Escherichia coli. Eugenol is further described to induce reactive oxygen species (ROS) production and to scavenge ROS, thus demonstrating prooxidant and antioxidant effects. Also, Eugenol is used as a pesticide.

CNS Activity

Sources: DOI: 10.2174/1573407210602010057

Originator

Sources: DOI: 10.1002/jlac.19194180105

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
DENTEK EUGENOL

Approved Use

For the temporary relief of throbbing, persistent toothache due to cavity.
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
174.8 μg × min/mL
20 mg/kg single, intravenous
dose: 20 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
EUGENOL plasma
Rattus norvegicus
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
19.4 min
20 mg/kg single, intravenous
dose: 20 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
EUGENOL plasma
Rattus norvegicus
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
4 % single, topical
Studied dose
Dose: 4 %
Route: topical
Route: single
Dose: 4 %
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
0.1 mL single, topical
Dose: 0.1 mL
Route: topical
Route: single
Dose: 0.1 mL
Sources:
unhealthy, CHILD
Health Status: unhealthy
Age Group: CHILD
Food Status: UNKNOWN
Sources:
OverviewDrug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no [IC50 3.9811 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
no
no
yes [Inhibition 10 uM]
yes [Inhibition 10 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
yes [Km 1570 uM]
yes [Km 1570 uM]
yes
yes
Sources: eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNzQzMzE2IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDQyNzEwIn19
yes
yes
yes
yes
Tox targets
PubMed

PubMed

TitleDatePubMed
In vitro human T cell sensitization to haptens by monocyte-derived dendritic cells.
2000 Dec
Anethole blocks both early and late cellular responses transduced by tumor necrosis factor: effect on NF-kappaB, AP-1, JNK, MAPKK and apoptosis.
2000 Jun 8
In vitro and in vivo activity of eugenol on human herpesvirus.
2000 Nov
Effects of isoeugenol on oxidative stress pathways in normal and streptozotocin-induced diabetic rats.
2001
Local anaesthetic activity of monoterpenes and phenylpropanes of essential oils.
2001 Aug
The effect of various root canal sealers on India ink and different concentrations of methylene blue solutions.
2001 Dec
Antimicrobial activity of four root canal sealers against endodontic pathogens.
2001 Dec
Capillary zone electrophoresis of coniferyl alcohol oxidation products.
2001 Dec
Functional magnetic resonance imaging of odor identification: the effect of aging.
2001 Dec
The effect of air-drying on glycosidically bound volatiles from seasonally collected origano (Origanum vulgare ssp. hirtum) from Croatia.
2001 Feb
Inhibitory effects of eugenol and thymol on Penicillium citrinum strains in culture media and cheese.
2001 Jul 20
Phytochemical constituents of Artemisia japonica ssp. littoricola.
2001 Jun
Structure-activity relationships for a large diverse set of natural, synthetic, and environmental estrogens.
2001 Mar
Poisoning with Boophane disticha: a forensic case.
2001 May
Allomonal and hepatotoxic effects following methyl eugenol consumption in Bactrocera papayae male against Gekko monarchus.
2001 May
Anti-genotoxicity of trans-anethole and eugenol in mice.
2001 May
Characterization of T cell responses to fragrances.
2001 May 1
Community of male Euglossini bees (Hymenoptera: Apidae) in a secondary forest, Alcântara, MA, Brazil.
2001 Nov
Antioxidant properties of 8.0.4'-neolignans.
2001 Nov
Quantitative analysis of detailed lignin monomer composition by pyrolysis-gas chromatography combined with preliminary acetylation of the samples.
2001 Nov 15
Spontaneous polymerisation on amphibole asbestos: relevance to asbestos removal.
2001 Nov 7
Quantitative gas chromatography-olfactometry carried out at different dilutions of an extract. Key differences in the odor profiles of four high-quality Spanish aged red wines.
2001 Oct
Comparative effects of eugenol to bis-eugenol on oral mucous membranes.
2001 Sep
Aerosolized essential oils and individual natural product compounds as brown treesnake repellents.
2002 Aug
O-methyltransferases involved in the biosynthesis of volatile phenolic derivatives in rose petals.
2002 Aug
Use of a B cell marker (B220) to discriminate between allergens and irritants in the local lymph node assay.
2002 Aug
Conservation and diversity of gene families explored using the CODEHOP strategy in higher plants.
2002 Aug 1
Antioxidant and prooxidant action of eugenol-related compounds and their cytotoxicity.
2002 Aug 1
Characterization of phenylpropene O-methyltransferases from sweet basil: facile change of substrate specificity and convergent evolution within a plant O-methyltransferase family.
2002 Feb
Inducing the cell cycle arrest and apoptosis of oral KB carcinoma cells by hydroxychavicol: roles of glutathione and reactive oxygen species.
2002 Feb
Inhibition of listeriolysin O and phosphatidylcholine-specific production in Listeria monocytogenes by subinhibitory concentrations of plant essential oils.
2002 Jul
In vitro effect of eugenol and cinnamaldehyde on membrane potential and respiratory chain complexes in isolated rat liver mitochondria.
2002 Jul
Safety assessment of allylalkoxybenzene derivatives used as flavouring substances - methyl eugenol and estragole.
2002 Jul
Chemosensory input and lateralization of brain function in the domestic chick.
2002 Jul 18
Effect of drying method on the volatiles in bay leaf (Laurus nobilis L.).
2002 Jul 31
Assessment of coronal microleakage in intermediately restored endodontic access cavities.
2002 Jun
Character impact odorants of the apple cultivars Elstar and Cox Orange.
2002 Jun
Phenotypic alterations and IL-1beta production in CD34(+) progenitor- and monocyte-derived dendritic cells after exposure to allergens: a comparative analysis.
2002 May
Accuracy of check-bite registration and centric condylar position.
2002 May
Extractives content in cooperage oak wood during natural seasoning and toasting; influence of tree species, geographic location, and single-tree effects.
2002 Oct 9
Adverse reactions associated with the use of eugenol in dentistry.
2002 Sep 14
Enzymatic synthesis of aroma compound xylosides using transfer reaction by Trichoderma longibrachiatum xylanase.
2002 Sep 25
Patents

Sample Use Guides

Rinse tooth with water to remove any food particles from the cavity. Moisten a cotton pellet with 1 or 2 drops of medication and using the tweezer, place in the cavity for approximately 1 minute. Avoid touching tissues other than the tooth cavity . Apply the dose not more than four times daily.
Route of Administration: Dental
Eugenol displayed in vitro activity against C. albicans cells within biofilms, when MIC(50) for sessile cells was 500 mg/L. C. albicans adherent cell populations (after 0, 1, 2 and 4 h of adherence) were treated with various concentrations of eugenol (0, 20, 200 and 2,000 mg/L). The extent of subsequent biofilm formation were then assessed with the tetrazolium salt reduction assay. Effect of eugenol on morphogenesis of C. albicans cells was observed by scanning electron microscopy (SEM). The results indicated that the effect of eugenol on adherent cells and subsequent biofilm formation was dependent on the initial adherence time and the concentration of this compound, and that eugenol can inhibit filamentous growth of C. albicans cells.
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:35:02 GMT 2025
Edited
by admin
on Mon Mar 31 17:35:02 GMT 2025
Record UNII
3T8H1794QW
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BIOXEDA
Preferred Name English
EUGENOL
EP   FCC   FHFI   HSDB   II   INCI   MART.   MI   USP   USP-RS   VANDF   WHO-DD  
INCI  
Official Name English
NSC-209525
Code English
EUGENOL [USP-RS]
Common Name English
FEMA NO. 2467
Code English
PHENOL, 2-METHOXY-4-(2-PROPENYL)-
Systematic Name English
4-Allyl-2-methoxyphenol
Systematic Name English
2-METHOXY-4-(2-PROPEN-1-YL)PHENOL
Systematic Name English
EUGENOL [HSDB]
Common Name English
EUGENOL (CONSTITUENT OF CINNAMOMUM VERUM BARK) [DSC]
Common Name English
4-ALLYLGUAIACOL
Systematic Name English
EUGENOL (CONSTITUENT OF HOLY BASIL LEAF) [DSC]
Common Name English
EUGENOL [VANDF]
Common Name English
EUGENOL [MART.]
Common Name English
EUGENOL [EP MONOGRAPH]
Common Name English
EUGENOL (CONSTITUENT OF CINNAMOMUM CASSIA BARK) [DSC]
Common Name English
4-ALLYLCATECHOL 2-METHYL ETHER
Common Name English
EUGENOL [IARC]
Common Name English
EUGENOL [FHFI]
Common Name English
Eugenol [WHO-DD]
Common Name English
1-HYDROXY-2-METHOXY-4-ALLYLBENZENE
Systematic Name English
EUGENOL [FCC]
Common Name English
EUGENOL [MI]
Common Name English
DENTOGUM
Common Name English
CARYOPHILLIC ACID
Common Name English
EUGENOL [USP MONOGRAPH]
Common Name English
NSC-8895
Code English
EUGENOL [II]
Common Name English
Classification Tree Code System Code
EC SCIENTIFIC COMMITTEE ON CONSUMER SAFETY OPINION SCCS/1459/11
Created by admin on Mon Mar 31 17:35:02 GMT 2025 , Edited by admin on Mon Mar 31 17:35:02 GMT 2025
DSLD 2902 (Number of products:13)
Created by admin on Mon Mar 31 17:35:02 GMT 2025 , Edited by admin on Mon Mar 31 17:35:02 GMT 2025
NCI_THESAURUS C245
Created by admin on Mon Mar 31 17:35:02 GMT 2025 , Edited by admin on Mon Mar 31 17:35:02 GMT 2025
JECFA EVALUATION EUGENOL
Created by admin on Mon Mar 31 17:35:02 GMT 2025 , Edited by admin on Mon Mar 31 17:35:02 GMT 2025
NDF-RT N0000185508
Created by admin on Mon Mar 31 17:35:02 GMT 2025 , Edited by admin on Mon Mar 31 17:35:02 GMT 2025
EPA PESTICIDE CODE 102701
Created by admin on Mon Mar 31 17:35:02 GMT 2025 , Edited by admin on Mon Mar 31 17:35:02 GMT 2025
Code System Code Type Description
ALANWOOD
eugenol
Created by admin on Mon Mar 31 17:35:02 GMT 2025 , Edited by admin on Mon Mar 31 17:35:02 GMT 2025
PRIMARY
SMS_ID
100000078677
Created by admin on Mon Mar 31 17:35:02 GMT 2025 , Edited by admin on Mon Mar 31 17:35:02 GMT 2025
PRIMARY
EPA CompTox
DTXSID9020617
Created by admin on Mon Mar 31 17:35:02 GMT 2025 , Edited by admin on Mon Mar 31 17:35:02 GMT 2025
PRIMARY
RXCUI
4186
Created by admin on Mon Mar 31 17:35:02 GMT 2025 , Edited by admin on Mon Mar 31 17:35:02 GMT 2025
PRIMARY RxNorm
NDF-RT
N0000175629
Created by admin on Mon Mar 31 17:35:02 GMT 2025 , Edited by admin on Mon Mar 31 17:35:02 GMT 2025
PRIMARY Increased Histamine Release [PE]
CHEBI
4917
Created by admin on Mon Mar 31 17:35:02 GMT 2025 , Edited by admin on Mon Mar 31 17:35:02 GMT 2025
PRIMARY
CAS
97-53-0
Created by admin on Mon Mar 31 17:35:02 GMT 2025 , Edited by admin on Mon Mar 31 17:35:02 GMT 2025
PRIMARY
HSDB
210
Created by admin on Mon Mar 31 17:35:02 GMT 2025 , Edited by admin on Mon Mar 31 17:35:02 GMT 2025
PRIMARY
DRUG BANK
DB09086
Created by admin on Mon Mar 31 17:35:02 GMT 2025 , Edited by admin on Mon Mar 31 17:35:02 GMT 2025
PRIMARY
ECHA (EC/EINECS)
202-589-1
Created by admin on Mon Mar 31 17:35:02 GMT 2025 , Edited by admin on Mon Mar 31 17:35:02 GMT 2025
PRIMARY
NDF-RT
N0000184306
Created by admin on Mon Mar 31 17:35:02 GMT 2025 , Edited by admin on Mon Mar 31 17:35:02 GMT 2025
PRIMARY Cell-mediated Immunity [PE]
DAILYMED
3T8H1794QW
Created by admin on Mon Mar 31 17:35:02 GMT 2025 , Edited by admin on Mon Mar 31 17:35:02 GMT 2025
PRIMARY
PUBCHEM
3314
Created by admin on Mon Mar 31 17:35:02 GMT 2025 , Edited by admin on Mon Mar 31 17:35:02 GMT 2025
PRIMARY
NSC
209525
Created by admin on Mon Mar 31 17:35:02 GMT 2025 , Edited by admin on Mon Mar 31 17:35:02 GMT 2025
PRIMARY
MESH
D005054
Created by admin on Mon Mar 31 17:35:02 GMT 2025 , Edited by admin on Mon Mar 31 17:35:02 GMT 2025
PRIMARY
DRUG CENTRAL
4648
Created by admin on Mon Mar 31 17:35:02 GMT 2025 , Edited by admin on Mon Mar 31 17:35:02 GMT 2025
PRIMARY
JECFA MONOGRAPH
1520
Created by admin on Mon Mar 31 17:35:02 GMT 2025 , Edited by admin on Mon Mar 31 17:35:02 GMT 2025
PRIMARY
RS_ITEM_NUM
1268965
Created by admin on Mon Mar 31 17:35:02 GMT 2025 , Edited by admin on Mon Mar 31 17:35:02 GMT 2025
PRIMARY
NSC
8895
Created by admin on Mon Mar 31 17:35:02 GMT 2025 , Edited by admin on Mon Mar 31 17:35:02 GMT 2025
PRIMARY
FDA UNII
3T8H1794QW
Created by admin on Mon Mar 31 17:35:02 GMT 2025 , Edited by admin on Mon Mar 31 17:35:02 GMT 2025
PRIMARY
EVMPD
SUB13776MIG
Created by admin on Mon Mar 31 17:35:02 GMT 2025 , Edited by admin on Mon Mar 31 17:35:02 GMT 2025
PRIMARY
ChEMBL
CHEMBL42710
Created by admin on Mon Mar 31 17:35:02 GMT 2025 , Edited by admin on Mon Mar 31 17:35:02 GMT 2025
PRIMARY
MERCK INDEX
m5210
Created by admin on Mon Mar 31 17:35:02 GMT 2025 , Edited by admin on Mon Mar 31 17:35:02 GMT 2025
PRIMARY Merck Index
NCI_THESAURUS
C75095
Created by admin on Mon Mar 31 17:35:02 GMT 2025 , Edited by admin on Mon Mar 31 17:35:02 GMT 2025
PRIMARY
NDF-RT
N0000171131
Created by admin on Mon Mar 31 17:35:02 GMT 2025 , Edited by admin on Mon Mar 31 17:35:02 GMT 2025
PRIMARY Allergens [Chemical/Ingredient]
WIKIPEDIA
EUGENOL
Created by admin on Mon Mar 31 17:35:02 GMT 2025 , Edited by admin on Mon Mar 31 17:35:02 GMT 2025
PRIMARY
Related Record Type Details
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