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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.
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
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
Antimicrobial activity of four root canal sealers against endodontic pathogens.
2001 Dec
Measurement of urinary methoxyphenols and their use for biological monitoring of wood smoke exposure.
2001 Feb
Evaluation of eugenol allergy in a patch-test population.
2001 Jan
Inhibitory effects of eugenol and thymol on Penicillium citrinum strains in culture media and cheese.
2001 Jul 20
Formaldehyde release from ground root canal sealer in vitro.
2001 Jun
Contact allergy to balsam of Peru. II. Patch test results in 102 patients with selected balsam of Peru constituents.
2001 Jun
Structure-activity relationships for a large diverse set of natural, synthetic, and environmental estrogens.
2001 Mar
In vitro bacterial penetration of endodontically treated teeth coronally sealed with a dentin bonding agent.
2001 May
Quantitative analysis of detailed lignin monomer composition by pyrolysis-gas chromatography combined with preliminary acetylation of the samples.
2001 Nov 15
Influence of eugenol-containing temporary restorations on bond strength of composite to dentin.
2001 Nov-Dec
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
Characterization of the eugenol hydroxylase genes (ehyA/ehyB) from the new eugenol-degrading Pseudomonas sp. strain OPS1.
2001 Sep
Cytotoxic evaluation of root canal filling materials on primary human oral fibroblast cultures and a permanent hamster cell line.
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
Occupational respiratory hypersensitivity in dental personnel.
2002 Apr
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
Fragrance as an occupational allergen.
2002 Feb
Safety assessment of allylalkoxybenzene derivatives used as flavouring substances - methyl eugenol and estragole.
2002 Jul
Effect of drying method on the volatiles in bay leaf (Laurus nobilis L.).
2002 Jul 31
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
Phenotypic alterations and IL-1beta production in CD34(+) progenitor- and monocyte-derived dendritic cells after exposure to allergens: a comparative analysis.
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
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 Dec 15 15:00:36 GMT 2023
Edited
by admin
on Fri Dec 15 15:00:36 GMT 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 Fri Dec 15 15:00:36 GMT 2023 , Edited by admin on Fri Dec 15 15:00:36 GMT 2023
DSLD 2902 (Number of products:13)
Created by admin on Fri Dec 15 15:00:36 GMT 2023 , Edited by admin on Fri Dec 15 15:00:36 GMT 2023
NCI_THESAURUS C245
Created by admin on Fri Dec 15 15:00:36 GMT 2023 , Edited by admin on Fri Dec 15 15:00:36 GMT 2023
JECFA EVALUATION EUGENOL
Created by admin on Fri Dec 15 15:00:36 GMT 2023 , Edited by admin on Fri Dec 15 15:00:36 GMT 2023
NDF-RT N0000185508
Created by admin on Fri Dec 15 15:00:36 GMT 2023 , Edited by admin on Fri Dec 15 15:00:36 GMT 2023
EPA PESTICIDE CODE 102701
Created by admin on Fri Dec 15 15:00:36 GMT 2023 , Edited by admin on Fri Dec 15 15:00:36 GMT 2023
Code System Code Type Description
ALANWOOD
eugenol
Created by admin on Fri Dec 15 15:00:36 GMT 2023 , Edited by admin on Fri Dec 15 15:00:36 GMT 2023
PRIMARY
SMS_ID
100000078677
Created by admin on Fri Dec 15 15:00:36 GMT 2023 , Edited by admin on Fri Dec 15 15:00:36 GMT 2023
PRIMARY
EPA CompTox
DTXSID9020617
Created by admin on Fri Dec 15 15:00:36 GMT 2023 , Edited by admin on Fri Dec 15 15:00:36 GMT 2023
PRIMARY
RXCUI
4186
Created by admin on Fri Dec 15 15:00:36 GMT 2023 , Edited by admin on Fri Dec 15 15:00:36 GMT 2023
PRIMARY RxNorm
NDF-RT
N0000175629
Created by admin on Fri Dec 15 15:00:36 GMT 2023 , Edited by admin on Fri Dec 15 15:00:36 GMT 2023
PRIMARY Increased Histamine Release [PE]
CHEBI
4917
Created by admin on Fri Dec 15 15:00:36 GMT 2023 , Edited by admin on Fri Dec 15 15:00:36 GMT 2023
PRIMARY
CAS
97-53-0
Created by admin on Fri Dec 15 15:00:36 GMT 2023 , Edited by admin on Fri Dec 15 15:00:36 GMT 2023
PRIMARY
HSDB
210
Created by admin on Fri Dec 15 15:00:36 GMT 2023 , Edited by admin on Fri Dec 15 15:00:36 GMT 2023
PRIMARY
DRUG BANK
DB09086
Created by admin on Fri Dec 15 15:00:36 GMT 2023 , Edited by admin on Fri Dec 15 15:00:36 GMT 2023
PRIMARY
ECHA (EC/EINECS)
202-589-1
Created by admin on Fri Dec 15 15:00:36 GMT 2023 , Edited by admin on Fri Dec 15 15:00:36 GMT 2023
PRIMARY
NDF-RT
N0000184306
Created by admin on Fri Dec 15 15:00:36 GMT 2023 , Edited by admin on Fri Dec 15 15:00:36 GMT 2023
PRIMARY Cell-mediated Immunity [PE]
DAILYMED
3T8H1794QW
Created by admin on Fri Dec 15 15:00:36 GMT 2023 , Edited by admin on Fri Dec 15 15:00:36 GMT 2023
PRIMARY
PUBCHEM
3314
Created by admin on Fri Dec 15 15:00:36 GMT 2023 , Edited by admin on Fri Dec 15 15:00:36 GMT 2023
PRIMARY
NSC
209525
Created by admin on Fri Dec 15 15:00:36 GMT 2023 , Edited by admin on Fri Dec 15 15:00:36 GMT 2023
PRIMARY
MESH
D005054
Created by admin on Fri Dec 15 15:00:36 GMT 2023 , Edited by admin on Fri Dec 15 15:00:36 GMT 2023
PRIMARY
DRUG CENTRAL
4648
Created by admin on Fri Dec 15 15:00:36 GMT 2023 , Edited by admin on Fri Dec 15 15:00:36 GMT 2023
PRIMARY
JECFA MONOGRAPH
1520
Created by admin on Fri Dec 15 15:00:36 GMT 2023 , Edited by admin on Fri Dec 15 15:00:36 GMT 2023
PRIMARY
RS_ITEM_NUM
1268965
Created by admin on Fri Dec 15 15:00:36 GMT 2023 , Edited by admin on Fri Dec 15 15:00:36 GMT 2023
PRIMARY
NSC
8895
Created by admin on Fri Dec 15 15:00:36 GMT 2023 , Edited by admin on Fri Dec 15 15:00:36 GMT 2023
PRIMARY
FDA UNII
3T8H1794QW
Created by admin on Fri Dec 15 15:00:36 GMT 2023 , Edited by admin on Fri Dec 15 15:00:36 GMT 2023
PRIMARY
EVMPD
SUB13776MIG
Created by admin on Fri Dec 15 15:00:36 GMT 2023 , Edited by admin on Fri Dec 15 15:00:36 GMT 2023
PRIMARY
ChEMBL
CHEMBL42710
Created by admin on Fri Dec 15 15:00:36 GMT 2023 , Edited by admin on Fri Dec 15 15:00:36 GMT 2023
PRIMARY
MERCK INDEX
m5210
Created by admin on Fri Dec 15 15:00:36 GMT 2023 , Edited by admin on Fri Dec 15 15:00:36 GMT 2023
PRIMARY Merck Index
NCI_THESAURUS
C75095
Created by admin on Fri Dec 15 15:00:36 GMT 2023 , Edited by admin on Fri Dec 15 15:00:36 GMT 2023
PRIMARY
NDF-RT
N0000171131
Created by admin on Fri Dec 15 15:00:36 GMT 2023 , Edited by admin on Fri Dec 15 15:00:36 GMT 2023
PRIMARY Allergens [Chemical/Ingredient]
WIKIPEDIA
EUGENOL
Created by admin on Fri Dec 15 15:00:36 GMT 2023 , Edited by admin on Fri Dec 15 15:00:36 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
ASSAY (GC)
PARENT -> CONSTITUENT MAY BE PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT MAY BE PRESENT
ASSAY (GC)
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
USP
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
ASSAY (GC)
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
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