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 |
|---|---|---|---|
Target ID: GO:1903409 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12126794 |
|||
Target ID: CHEMBL4794 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14514756 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | DENTEK EUGENOL Approved UseFor the temporary relief of throbbing, persistent toothache due to cavity. |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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: |
|
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 |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
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 |
|---|---|---|
| Extractives content in cooperage oak wood during natural seasoning and toasting; influence of tree species, geographic location, and single-tree effects. | 2002-10-09 |
|
| Enzymatic synthesis of aroma compound xylosides using transfer reaction by Trichoderma longibrachiatum xylanase. | 2002-09-25 |
|
| Adverse reactions associated with the use of eugenol in dentistry. | 2002-09-14 |
|
| Conservation and diversity of gene families explored using the CODEHOP strategy in higher plants. | 2002-08-01 |
|
| Antioxidant and prooxidant action of eugenol-related compounds and their cytotoxicity. | 2002-08-01 |
|
| Aerosolized essential oils and individual natural product compounds as brown treesnake repellents. | 2002-08 |
|
| O-methyltransferases involved in the biosynthesis of volatile phenolic derivatives in rose petals. | 2002-08 |
|
| Use of a B cell marker (B220) to discriminate between allergens and irritants in the local lymph node assay. | 2002-08 |
|
| Effect of drying method on the volatiles in bay leaf (Laurus nobilis L.). | 2002-07-31 |
|
| Chemosensory input and lateralization of brain function in the domestic chick. | 2002-07-18 |
|
| Inhibition of listeriolysin O and phosphatidylcholine-specific production in Listeria monocytogenes by subinhibitory concentrations of plant essential oils. | 2002-07 |
|
| In vitro effect of eugenol and cinnamaldehyde on membrane potential and respiratory chain complexes in isolated rat liver mitochondria. | 2002-07 |
|
| Safety assessment of allylalkoxybenzene derivatives used as flavouring substances - methyl eugenol and estragole. | 2002-07 |
|
| Multicentre study of fragrance allergy in Hungary. Immediate and late type reactions. | 2002-06 |
|
| Assessment of coronal microleakage in intermediately restored endodontic access cavities. | 2002-06 |
|
| Character impact odorants of the apple cultivars Elstar and Cox Orange. | 2002-06 |
|
| Transcriptional control of monolignol biosynthesis in Pinus taeda: factors affecting monolignol ratios and carbon allocation in phenylpropanoid metabolism. | 2002-05-24 |
|
| Molecular cloning and characterisation of three new ATP-binding cassette transporter genes from the wheat pathogen Mycosphaerella graminicola. | 2002-05-01 |
|
| Inhibition of intestinal motility by methanol extracts of Hibiscus sabdariffa L. (Malvaceae) in rats. | 2002-05 |
|
| In vitro antifungal activity of several antimicrobial compounds against Penicillium expansum. | 2002-05 |
|
| Phenotypic alterations and IL-1beta production in CD34(+) progenitor- and monocyte-derived dendritic cells after exposure to allergens: a comparative analysis. | 2002-05 |
|
| Accuracy of check-bite registration and centric condylar position. | 2002-05 |
|
| Influence of oak wood on the aromatic composition and quality of wines with different tannin contents. | 2002-04-24 |
|
| Effect of three root canal sealers on the retentive strength of endodontic posts luted with a resin cement. | 2002-04 |
|
| Anticonvulsant activity of the leaf essential oil of Laurus nobilis against pentylenetetrazole- and maximal electroshock-induced seizures. | 2002-04 |
|
| Leakage of interim post and cores used during laboratory fabrication of custom posts. | 2002-04 |
|
| Occupational respiratory hypersensitivity in dental personnel. | 2002-04 |
|
| Spice oils for the control of co-occurring mycotoxin-producing fungi. | 2002-04 |
|
| Antitermitic activity of leaf essential oils and components from Cinnamomum osmophleum. | 2002-03-13 |
|
| Effect of dowel space preparation and composite cement thickness on retention of a prefabricated dowel. | 2002-03 |
|
| Aspergillus flavus dose-response curves to selected natural and synthetic antimicrobials. | 2002-03 |
|
| Authenticity assessment of estragole and methyl eugenol by on-line gas chromatography-isotope ratio mass spectrometry. | 2002-02-27 |
|
| Methyleugenol and eugenol variation in Ocimum basilicum cv. Genovese gigante grown in greenhouse and in vitro. | 2002-02-02 |
|
| Population dynamics of euglossinae bees (Hymenoptera, Apidae) in an early second-growth forest of Cajual Island, in the state of Maranhão, Brazil. | 2002-02 |
|
| Comparison of adult corn rootworm (Coleoptera: Chrysomelidae) sampling methods. | 2002-02 |
|
| Characterization of phenylpropene O-methyltransferases from sweet basil: facile change of substrate specificity and convergent evolution within a plant O-methyltransferase family. | 2002-02 |
|
| Fragrance as an occupational allergen. | 2002-02 |
|
| Inducing the cell cycle arrest and apoptosis of oral KB carcinoma cells by hydroxychavicol: roles of glutathione and reactive oxygen species. | 2002-02 |
|
| The effects of eugenol and epoxy-resin on the strength of a hybrid composite resin. | 2002-02 |
|
| Inhibition of human low density lipoprotein oxidation by active principles from spices. | 2002-01 |
|
| The effect of various root canal sealers on India ink and different concentrations of methylene blue solutions. | 2001-12 |
|
| Antimicrobial activity of four root canal sealers against endodontic pathogens. | 2001-12 |
|
| Capillary zone electrophoresis of coniferyl alcohol oxidation products. | 2001-12 |
|
| Functional magnetic resonance imaging of odor identification: the effect of aging. | 2001-12 |
|
| Quantitative analysis of detailed lignin monomer composition by pyrolysis-gas chromatography combined with preliminary acetylation of the samples. | 2001-11-15 |
|
| Spontaneous polymerisation on amphibole asbestos: relevance to asbestos removal. | 2001-11-07 |
|
| Community of male Euglossini bees (Hymenoptera: Apidae) in a secondary forest, Alcântara, MA, Brazil. | 2001-11 |
|
| Antioxidant properties of 8.0.4'-neolignans. | 2001-11 |
|
| Comparative effects of eugenol to bis-eugenol on oral mucous membranes. | 2001-09 |
|
| [New data on composition of esssential oil from inflorescence of everlasting (Helichrysum arenarium(L.) Moench.)]. | 2001-08 |
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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| 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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PRIMARY | |||
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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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PRIMARY | |||
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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 |