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Details

Stereochemistry ACHIRAL
Molecular Formula C10H12O2
Molecular Weight 164.2015
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of EUGENOL

SMILES

C=CCc1ccc(c(c1)OC)O

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 164.2015
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.
PubMed

PubMed

TitleDatePubMed
Effects of isoeugenol on oxidative stress pathways in normal and streptozotocin-induced diabetic rats.
2001
Evaluation of volatile chemical treatments for lethality to Salmonella on alfalfa seeds and sprouts.
2001 Apr
Methyleugenol and eugenol variation in Ocimum basilicum cv. Genovese gigante grown in greenhouse and in vitro.
2001 Apr-Jun
[New data on composition of esssential oil from inflorescence of everlasting (Helichrysum arenarium(L.) Moench.)].
2001 Aug
Lack of modifying effects of eugenol on development of lung proliferative lesions induced by urethane in transgenic mice carrying the human prototype c-Ha-ras gene.
2001 Aug
Biotechnological production of vanillin.
2001 Aug
Oxidation of cinnamyl alcohols and aldehydes by a basic peroxidase from lignifying Zinnia elegans hypocotyls.
2001 Aug
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
Contact allergy to balsam of Peru. II. Patch test results in 102 patients with selected balsam of Peru constituents.
2001 Jun
Comparative efficacy of tricaine methanesulfonate and clove oil for use as anesthetics in red pacu (Piaractus brachypomus).
2001 Mar
Evaluation of the developmental toxicity of isoeugenol in Sprague-Dawley (CD) rats.
2001 Mar
Investigation of the role of the 2',3'-epoxidation pathway in the bioactivation and genotoxicity of dietary allylbenzene analogs.
2001 Mar 7
In vitro bacterial penetration of endodontically treated teeth coronally sealed with a dentin bonding agent.
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
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
Glycosides and xanthine oxidase inhibitors from Conyza bonariensis.
2001 Oct
Characterization of the eugenol hydroxylase genes (ehyA/ehyB) from the new eugenol-degrading Pseudomonas sp. strain OPS1.
2001 Sep
Differential activity and structure of highly similar peroxidases. Spectroscopic, crystallographic, and enzymatic analyses of lignifying Arabidopsis thaliana peroxidase A2 and horseradish peroxidase A2.
2001 Sep 18
Occupational respiratory hypersensitivity in dental personnel.
2002 Apr
Influence of oak wood on the aromatic composition and quality of wines with different tannin contents.
2002 Apr 24
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
Population dynamics of euglossinae bees (Hymenoptera, Apidae) in an early second-growth forest of Cajual Island, in the state of Maranhão, Brazil.
2002 Feb
Comparison of adult corn rootworm (Coleoptera: Chrysomelidae) sampling methods.
2002 Feb
Characterization of phenylpropene O-methyltransferases from sweet basil: facile change of substrate specificity and convergent evolution within a plant O-methyltransferase family.
2002 Feb
Fragrance as an occupational allergen.
2002 Feb
Authenticity assessment of estragole and methyl eugenol by on-line gas chromatography-isotope ratio mass spectrometry.
2002 Feb 27
Inhibition of listeriolysin O and phosphatidylcholine-specific production in Listeria monocytogenes by subinhibitory concentrations of plant essential oils.
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
Multicentre study of fragrance allergy in Hungary. Immediate and late type reactions.
2002 Jun
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
Aspergillus flavus dose-response curves to selected natural and synthetic antimicrobials.
2002 Mar
Antitermitic activity of leaf essential oils and components from Cinnamomum osmophleum.
2002 Mar 13
Inhibition of intestinal motility by methanol extracts of Hibiscus sabdariffa L. (Malvaceae) in rats.
2002 May
In vitro antifungal activity of several antimicrobial compounds against Penicillium expansum.
2002 May
Accuracy of check-bite registration and centric condylar position.
2002 May
Transcriptional control of monolignol biosynthesis in Pinus taeda: factors affecting monolignol ratios and carbon allocation in phenylpropanoid metabolism.
2002 May 24
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 Fri Jun 25 21:18:16 UTC 2021
Edited
by admin
on Fri Jun 25 21:18:16 UTC 2021
Record UNII
3T8H1794QW
Record Status Validated (UNII)
Record Version
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Name Type Language
EUGENOL
EP   FCC   FHFI   HSDB   II   INCI   MART.   MI   USP   USP-RS   VANDF   WHO-DD  
INCI  
Official Name English
EUGENOL [USP]
Common 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
EUGENOL [INCI]
Common 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
BIOXEDA
Brand 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
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 Fri Jun 25 21:18:16 UTC 2021 , Edited by admin on Fri Jun 25 21:18:16 UTC 2021
DSLD 2902 (Number of products:13)
Created by admin on Fri Jun 25 21:18:16 UTC 2021 , Edited by admin on Fri Jun 25 21:18:16 UTC 2021
NCI_THESAURUS C245
Created by admin on Fri Jun 25 21:18:16 UTC 2021 , Edited by admin on Fri Jun 25 21:18:16 UTC 2021
JECFA EVALUATION EUGENOL
Created by admin on Fri Jun 25 21:18:16 UTC 2021 , Edited by admin on Fri Jun 25 21:18:16 UTC 2021
NDF-RT N0000185508
Created by admin on Fri Jun 25 21:18:16 UTC 2021 , Edited by admin on Fri Jun 25 21:18:16 UTC 2021
EPA PESTICIDE CODE 102701
Created by admin on Fri Jun 25 21:18:16 UTC 2021 , Edited by admin on Fri Jun 25 21:18:16 UTC 2021
Code System Code Type Description
EPA CompTox
97-53-0
Created by admin on Fri Jun 25 21:18:16 UTC 2021 , Edited by admin on Fri Jun 25 21:18:16 UTC 2021
PRIMARY
RXCUI
4186
Created by admin on Fri Jun 25 21:18:16 UTC 2021 , Edited by admin on Fri Jun 25 21:18:16 UTC 2021
PRIMARY RxNorm
NDF-RT
N0000175629
Created by admin on Fri Jun 25 21:18:16 UTC 2021 , Edited by admin on Fri Jun 25 21:18:16 UTC 2021
PRIMARY Increased Histamine Release [PE]
CAS
97-53-0
Created by admin on Fri Jun 25 21:18:16 UTC 2021 , Edited by admin on Fri Jun 25 21:18:16 UTC 2021
PRIMARY
HSDB
210
Created by admin on Fri Jun 25 21:18:16 UTC 2021 , Edited by admin on Fri Jun 25 21:18:16 UTC 2021
PRIMARY
DRUG BANK
DB09086
Created by admin on Fri Jun 25 21:18:16 UTC 2021 , Edited by admin on Fri Jun 25 21:18:16 UTC 2021
PRIMARY
ECHA (EC/EINECS)
202-589-1
Created by admin on Fri Jun 25 21:18:16 UTC 2021 , Edited by admin on Fri Jun 25 21:18:16 UTC 2021
PRIMARY
NDF-RT
N0000184306
Created by admin on Fri Jun 25 21:18:16 UTC 2021 , Edited by admin on Fri Jun 25 21:18:16 UTC 2021
PRIMARY Cell-mediated Immunity [PE]
PUBCHEM
3314
Created by admin on Fri Jun 25 21:18:16 UTC 2021 , Edited by admin on Fri Jun 25 21:18:16 UTC 2021
PRIMARY
MESH
D005054
Created by admin on Fri Jun 25 21:18:16 UTC 2021 , Edited by admin on Fri Jun 25 21:18:16 UTC 2021
PRIMARY
DRUG CENTRAL
4648
Created by admin on Fri Jun 25 21:18:16 UTC 2021 , Edited by admin on Fri Jun 25 21:18:16 UTC 2021
PRIMARY
FDA UNII
3T8H1794QW
Created by admin on Fri Jun 25 21:18:16 UTC 2021 , Edited by admin on Fri Jun 25 21:18:16 UTC 2021
PRIMARY
EVMPD
SUB13776MIG
Created by admin on Fri Jun 25 21:18:16 UTC 2021 , Edited by admin on Fri Jun 25 21:18:16 UTC 2021
PRIMARY
USP_CATALOG
1268965
Created by admin on Fri Jun 25 21:18:16 UTC 2021 , Edited by admin on Fri Jun 25 21:18:16 UTC 2021
PRIMARY USP-RS
ChEMBL
CHEMBL42710
Created by admin on Fri Jun 25 21:18:16 UTC 2021 , Edited by admin on Fri Jun 25 21:18:16 UTC 2021
PRIMARY
MERCK INDEX
M5210
Created by admin on Fri Jun 25 21:18:16 UTC 2021 , Edited by admin on Fri Jun 25 21:18:16 UTC 2021
PRIMARY Merck Index
NCI_THESAURUS
C75095
Created by admin on Fri Jun 25 21:18:16 UTC 2021 , Edited by admin on Fri Jun 25 21:18:16 UTC 2021
PRIMARY
NDF-RT
N0000171131
Created by admin on Fri Jun 25 21:18:16 UTC 2021 , Edited by admin on Fri Jun 25 21:18:16 UTC 2021
PRIMARY Allergens [Chemical/Ingredient]
WIKIPEDIA
EUGENOL
Created by admin on Fri Jun 25 21:18:16 UTC 2021 , Edited by admin on Fri Jun 25 21:18:16 UTC 2021
PRIMARY
Related Record Type Details
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.
PARENT -> CONSTITUENT ALWAYS PRESENT
ASSAY (GC)
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
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PARENT -> CONSTITUENT ALWAYS PRESENT
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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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