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
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
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 |
DescriptionSources: https://www.marinwater.org/DocumentCenter/View/253Curator'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
Sources: https://www.marinwater.org/DocumentCenter/View/253
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
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: GO:1903409 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12126794 |
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Target ID: CHEMBL4794 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14514756 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | DENTEK EUGENOL Approved UseFor the temporary relief of throbbing, persistent toothache due to cavity. |
AUC
Value | Dose | Co-administered | Analyte | Population |
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174.8 μg × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/36675321/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
19.4 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/36675321/ |
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
Dose | Population | Adverse events |
---|---|---|
4 % single, topical Studied dose |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
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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: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
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OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
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Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical 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] | ||||
Page: 315.0 |
no | |||
Page: 396.0 |
no | |||
yes [Inhibition 10 uM] | ||||
yes [Inhibition 10 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 388 | 393 |
no | |||
yes [Km 1570 uM] | ||||
yes [Km 1570 uM] | ||||
yes | ||||
yes | ||||
Sources: eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNzQzMzE2IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDQyNzEwIn19 |
yes | |||
yes | ||||
yes | ||||
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
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In vitro human T cell sensitization to haptens by monocyte-derived dendritic cells. | 2000 Dec |
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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 |
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In vitro and in vivo activity of eugenol on human herpesvirus. | 2000 Nov |
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Effects of isoeugenol on oxidative stress pathways in normal and streptozotocin-induced diabetic rats. | 2001 |
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Local anaesthetic activity of monoterpenes and phenylpropanes of essential oils. | 2001 Aug |
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The effect of various root canal sealers on India ink and different concentrations of methylene blue solutions. | 2001 Dec |
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Antimicrobial activity of four root canal sealers against endodontic pathogens. | 2001 Dec |
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Capillary zone electrophoresis of coniferyl alcohol oxidation products. | 2001 Dec |
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Functional magnetic resonance imaging of odor identification: the effect of aging. | 2001 Dec |
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The effect of air-drying on glycosidically bound volatiles from seasonally collected origano (Origanum vulgare ssp. hirtum) from Croatia. | 2001 Feb |
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Inhibitory effects of eugenol and thymol on Penicillium citrinum strains in culture media and cheese. | 2001 Jul 20 |
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Phytochemical constituents of Artemisia japonica ssp. littoricola. | 2001 Jun |
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Structure-activity relationships for a large diverse set of natural, synthetic, and environmental estrogens. | 2001 Mar |
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Poisoning with Boophane disticha: a forensic case. | 2001 May |
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Allomonal and hepatotoxic effects following methyl eugenol consumption in Bactrocera papayae male against Gekko monarchus. | 2001 May |
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Anti-genotoxicity of trans-anethole and eugenol in mice. | 2001 May |
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Characterization of T cell responses to fragrances. | 2001 May 1 |
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Community of male Euglossini bees (Hymenoptera: Apidae) in a secondary forest, Alcântara, MA, Brazil. | 2001 Nov |
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Antioxidant properties of 8.0.4'-neolignans. | 2001 Nov |
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Quantitative analysis of detailed lignin monomer composition by pyrolysis-gas chromatography combined with preliminary acetylation of the samples. | 2001 Nov 15 |
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Spontaneous polymerisation on amphibole asbestos: relevance to asbestos removal. | 2001 Nov 7 |
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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 |
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Comparative effects of eugenol to bis-eugenol on oral mucous membranes. | 2001 Sep |
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Aerosolized essential oils and individual natural product compounds as brown treesnake repellents. | 2002 Aug |
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O-methyltransferases involved in the biosynthesis of volatile phenolic derivatives in rose petals. | 2002 Aug |
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Use of a B cell marker (B220) to discriminate between allergens and irritants in the local lymph node assay. | 2002 Aug |
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Conservation and diversity of gene families explored using the CODEHOP strategy in higher plants. | 2002 Aug 1 |
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Antioxidant and prooxidant action of eugenol-related compounds and their cytotoxicity. | 2002 Aug 1 |
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Characterization of phenylpropene O-methyltransferases from sweet basil: facile change of substrate specificity and convergent evolution within a plant O-methyltransferase family. | 2002 Feb |
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Inducing the cell cycle arrest and apoptosis of oral KB carcinoma cells by hydroxychavicol: roles of glutathione and reactive oxygen species. | 2002 Feb |
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Inhibition of listeriolysin O and phosphatidylcholine-specific production in Listeria monocytogenes by subinhibitory concentrations of plant essential oils. | 2002 Jul |
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In vitro effect of eugenol and cinnamaldehyde on membrane potential and respiratory chain complexes in isolated rat liver mitochondria. | 2002 Jul |
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Safety assessment of allylalkoxybenzene derivatives used as flavouring substances - methyl eugenol and estragole. | 2002 Jul |
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Chemosensory input and lateralization of brain function in the domestic chick. | 2002 Jul 18 |
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Effect of drying method on the volatiles in bay leaf (Laurus nobilis L.). | 2002 Jul 31 |
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Assessment of coronal microleakage in intermediately restored endodontic access cavities. | 2002 Jun |
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Character impact odorants of the apple cultivars Elstar and Cox Orange. | 2002 Jun |
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Phenotypic alterations and IL-1beta production in CD34(+) progenitor- and monocyte-derived dendritic cells after exposure to allergens: a comparative analysis. | 2002 May |
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Accuracy of check-bite registration and centric condylar position. | 2002 May |
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Extractives content in cooperage oak wood during natural seasoning and toasting; influence of tree species, geographic location, and single-tree effects. | 2002 Oct 9 |
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Adverse reactions associated with the use of eugenol in dentistry. | 2002 Sep 14 |
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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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17356790
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
Edited
Mon Mar 31 17:35:02 GMT 2025
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on
Mon Mar 31 17:35:02 GMT 2025
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Record UNII |
3T8H1794QW
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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EC SCIENTIFIC COMMITTEE ON CONSUMER SAFETY OPINION |
SCCS/1459/11
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DSLD |
2902 (Number of products:13)
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NCI_THESAURUS |
C245
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JECFA EVALUATION |
EUGENOL
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NDF-RT |
N0000185508
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EPA PESTICIDE CODE |
102701
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Code System | Code | Type | Description | ||
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eugenol
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100000078677
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DTXSID9020617
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4186
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PRIMARY | RxNorm | ||
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N0000175629
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PRIMARY | Increased Histamine Release [PE] | ||
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4917
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97-53-0
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210
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DB09086
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202-589-1
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N0000184306
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PRIMARY | Cell-mediated Immunity [PE] | ||
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3T8H1794QW
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3314
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209525
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D005054
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4648
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1520
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1268965
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8895
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3T8H1794QW
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SUB13776MIG
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CHEMBL42710
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m5210
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PRIMARY | Merck Index | ||
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C75095
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N0000171131
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PRIMARY | Allergens [Chemical/Ingredient] | ||
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EUGENOL
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Related Record | Type | Details | ||
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PARENT -> CONSTITUENT MAY BE PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
A cinnamon leaf oil of Chinese origin, Cinnamomun japonicum Sieb., contains a high concentration of safrole (60%) and only about 3% eugenol.
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PARENT -> CONSTITUENT MAY BE PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
USP
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
In view of the toxic properties documented for the oil and associated with beta-asarone , it has been recommended that only beta-asarone-free calamus root should be used in phytotherapy.
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ACTIVE MOIETY |