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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

CNS Active
3828
Sources: DOI: 10.2174/1573407210602010057

Originator

Kremers, F.
1
Sources: DOI: 10.1002/jlac.19194180105

Approval Year

1921
1447
Targets

Targets

Primary TargetPharmacologyConditionPotency
Modulator
822
Agonist
2662
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8360
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
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
Anthelmintic activity of essential oil of Ocimum sanctum and eugenol.
2001 Aug
Oxidation of cinnamyl alcohols and aldehydes by a basic peroxidase from lignifying Zinnia elegans hypocotyls.
2001 Aug
The effect of various root canal sealers on India ink and different concentrations of methylene blue solutions.
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
Phytochemical constituents of Artemisia japonica ssp. littoricola.
2001 Jun
Identification and quantification of impact odorants of aged red wines from Rioja. GC-olfactometry, quantitative GC-MS, and odor evaluation of HPLC fractions.
2001 Jun
Contact allergy to balsam of Peru. II. Patch test results in 102 patients with selected balsam of Peru constituents.
2001 Jun
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
Antioxidant properties of 8.0.4'-neolignans.
2001 Nov
Insecticidal activity of essential oils: octopaminergic sites of action.
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
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
Modification of fatty acids changes the flavor volatiles in tomato leaves.
2001 Sep
Leakage of interim post and cores used during laboratory fabrication of custom posts.
2002 Apr
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
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
The effects of eugenol and epoxy-resin on the strength of a hybrid composite resin.
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
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
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
Molecular cloning and characterisation of three new ATP-binding cassette transporter genes from the wheat pathogen Mycosphaerella graminicola.
2002 May 1
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

Patents

04048236
2
05358861
1
07022664
1
07906549
1
08846721
1
JP2000096078A
2
JP2000344641A
3
JP2001131037A
1
JP2001163715A
1
JP2002003351A
1
JP2002087973A
1
JP2002511777A
412
JP2004359602A
2
JP2004532087A
1
JP2005002130A
2
JP2006081461A
1
JP2007325584A
1
JP2008110951A
2
JP2008266319A
5
JP2008509189A
188
JP2009011320A
2
JP2009531121A
10
JP2542801B2
1
JP3302374B2
1
JP3851351B2
2
JP4140829B2
2
JPH01265042A
3
JPH02196718A
8
JPH03234797A
4
JPH03263481A
4
JPH05236972A
4
JPH05255007A
3
JPH05320032A
2
JPH06178660A
2
JPH07228711A
2
JPH09151253A
1
JPH09154930A
1
JPH09241139A
2
JPH10139637A
2
JPH10155496A
2
JPH11228368A
3
JPS57106697A
1
JPS5865207A
1
JPS61171758A
5
JPS63277612A
1
JPS6372654A
5

Sample Use Guides

In Vivo Use Guide
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
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 Wed Jul 05 22:32:40 UTC 2023
Edited
by admin
on Wed Jul 05 22:32:40 UTC 2023
Record UNII
3T8H1794QW
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
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
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
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 Wed Jul 05 22:32:40 UTC 2023 , Edited by admin on Wed Jul 05 22:32:40 UTC 2023
DSLD 2902 (Number of products:13)
Created by admin on Wed Jul 05 22:32:40 UTC 2023 , Edited by admin on Wed Jul 05 22:32:40 UTC 2023
NCI_THESAURUS C245
Created by admin on Wed Jul 05 22:32:40 UTC 2023 , Edited by admin on Wed Jul 05 22:32:40 UTC 2023
JECFA EVALUATION EUGENOL
Created by admin on Wed Jul 05 22:32:40 UTC 2023 , Edited by admin on Wed Jul 05 22:32:40 UTC 2023
NDF-RT N0000185508
Created by admin on Wed Jul 05 22:32:40 UTC 2023 , Edited by admin on Wed Jul 05 22:32:40 UTC 2023
EPA PESTICIDE CODE 102701
Created by admin on Wed Jul 05 22:32:40 UTC 2023 , Edited by admin on Wed Jul 05 22:32:40 UTC 2023
Code System Code Type Description
ALANWOOD
eugenol
Created by admin on Wed Jul 05 22:32:40 UTC 2023 , Edited by admin on Wed Jul 05 22:32:40 UTC 2023
PRIMARY
SMS_ID
100000078677
Created by admin on Wed Jul 05 22:32:40 UTC 2023 , Edited by admin on Wed Jul 05 22:32:40 UTC 2023
PRIMARY
EPA CompTox
DTXSID9020617
Created by admin on Wed Jul 05 22:32:40 UTC 2023 , Edited by admin on Wed Jul 05 22:32:40 UTC 2023
PRIMARY
RXCUI
4186
Created by admin on Wed Jul 05 22:32:40 UTC 2023 , Edited by admin on Wed Jul 05 22:32:40 UTC 2023
PRIMARY RxNorm
NDF-RT
N0000175629
Created by admin on Wed Jul 05 22:32:40 UTC 2023 , Edited by admin on Wed Jul 05 22:32:40 UTC 2023
PRIMARY Increased Histamine Release [PE]
CHEBI
4917
Created by admin on Wed Jul 05 22:32:40 UTC 2023 , Edited by admin on Wed Jul 05 22:32:40 UTC 2023
PRIMARY
CAS
97-53-0
Created by admin on Wed Jul 05 22:32:40 UTC 2023 , Edited by admin on Wed Jul 05 22:32:40 UTC 2023
PRIMARY
HSDB
210
Created by admin on Wed Jul 05 22:32:40 UTC 2023 , Edited by admin on Wed Jul 05 22:32:40 UTC 2023
PRIMARY
DRUG BANK
DB09086
Created by admin on Wed Jul 05 22:32:40 UTC 2023 , Edited by admin on Wed Jul 05 22:32:40 UTC 2023
PRIMARY
ECHA (EC/EINECS)
202-589-1
Created by admin on Wed Jul 05 22:32:40 UTC 2023 , Edited by admin on Wed Jul 05 22:32:40 UTC 2023
PRIMARY
NDF-RT
N0000184306
Created by admin on Wed Jul 05 22:32:40 UTC 2023 , Edited by admin on Wed Jul 05 22:32:40 UTC 2023
PRIMARY Cell-mediated Immunity [PE]
DAILYMED
3T8H1794QW
Created by admin on Wed Jul 05 22:32:40 UTC 2023 , Edited by admin on Wed Jul 05 22:32:40 UTC 2023
PRIMARY
PUBCHEM
3314
Created by admin on Wed Jul 05 22:32:40 UTC 2023 , Edited by admin on Wed Jul 05 22:32:40 UTC 2023
PRIMARY
NSC
209525
Created by admin on Wed Jul 05 22:32:40 UTC 2023 , Edited by admin on Wed Jul 05 22:32:40 UTC 2023
PRIMARY
MESH
D005054
Created by admin on Wed Jul 05 22:32:40 UTC 2023 , Edited by admin on Wed Jul 05 22:32:40 UTC 2023
PRIMARY
DRUG CENTRAL
4648
Created by admin on Wed Jul 05 22:32:40 UTC 2023 , Edited by admin on Wed Jul 05 22:32:40 UTC 2023
PRIMARY
RS_ITEM_NUM
1268965
Created by admin on Wed Jul 05 22:32:40 UTC 2023 , Edited by admin on Wed Jul 05 22:32:40 UTC 2023
PRIMARY
NSC
8895
Created by admin on Wed Jul 05 22:32:40 UTC 2023 , Edited by admin on Wed Jul 05 22:32:40 UTC 2023
PRIMARY
FDA UNII
3T8H1794QW
Created by admin on Wed Jul 05 22:32:40 UTC 2023 , Edited by admin on Wed Jul 05 22:32:40 UTC 2023
PRIMARY
EVMPD
SUB13776MIG
Created by admin on Wed Jul 05 22:32:40 UTC 2023 , Edited by admin on Wed Jul 05 22:32:40 UTC 2023
PRIMARY
ChEMBL
CHEMBL42710
Created by admin on Wed Jul 05 22:32:40 UTC 2023 , Edited by admin on Wed Jul 05 22:32:40 UTC 2023
PRIMARY
MERCK INDEX
M5210
Created by admin on Wed Jul 05 22:32:40 UTC 2023 , Edited by admin on Wed Jul 05 22:32:40 UTC 2023
PRIMARY Merck Index
NCI_THESAURUS
C75095
Created by admin on Wed Jul 05 22:32:40 UTC 2023 , Edited by admin on Wed Jul 05 22:32:40 UTC 2023
PRIMARY
NDF-RT
N0000171131
Created by admin on Wed Jul 05 22:32:40 UTC 2023 , Edited by admin on Wed Jul 05 22:32:40 UTC 2023
PRIMARY Allergens [Chemical/Ingredient]
WIKIPEDIA
EUGENOL
Created by admin on Wed Jul 05 22:32:40 UTC 2023 , Edited by admin on Wed Jul 05 22:32:40 UTC 2023
PRIMARY
Related Record Type Details
CHINESE CINNAMON LEAF OIL
PARENT -> CONSTITUENT MAY BE PRESENT
CYNARA SCOLYMUS LEAF
PARENT -> CONSTITUENT ALWAYS PRESENT
CHINESE CINNAMON LEAF OIL
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.
CINNAMON BARK OIL
PARENT -> CONSTITUENT MAY BE PRESENT
ASSAY (GC)
GEUM URBANUM WHOLE
PARENT -> CONSTITUENT ALWAYS PRESENT
HOLY BASIL LEAF
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
CHINESE CINNAMON
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
CINNAMON
PARENT -> CONSTITUENT ALWAYS PRESENT
CINNAMON LEAF OIL
PARENT -> CONSTITUENT ALWAYS PRESENT
ASSAY (GC)
CLOVE OIL
PARENT -> CONSTITUENT ALWAYS PRESENT
ASSAY (GC)
ACORUS CALAMUS ROOT
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.
Related Record Type Details
Structure of EUGENOL
ACTIVE MOIETY
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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