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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
3897
Sources: DOI: 10.2174/1573407210602010057

Originator

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

Approval Year

1921
1447
Targets

Targets

Primary TargetPharmacologyConditionPotency
Modulator
817
Agonist
2637
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8307
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
Anthelmintic activity of essential oil of Ocimum sanctum and eugenol.
2001 Aug
Suppression of chemical mutagen-induced SOS response by alkylphenols from clove (Syzygium aromaticum) in the Salmonella typhimurium TA1535/pSK1002 umu test.
2001 Aug
Langerhans cells and immature dendritic cells as model systems for screening of skin sensitizers.
2001 Aug-Oct
The effect of various root canal sealers on India ink and different concentrations of methylene blue solutions.
2001 Dec
Measurement of urinary methoxyphenols and their use for biological monitoring of wood smoke exposure.
2001 Feb
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
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
Reactive oxygen species generation and photo-cytotoxicity of eugenol in solutions of various pH.
2001 Jun
Structure-activity relationships for a large diverse set of natural, synthetic, and environmental estrogens.
2001 Mar
Evaluation of the developmental toxicity of isoeugenol in Sprague-Dawley (CD) rats.
2001 Mar
Root canal sealers cause cytotoxicity and oxidative damage in hepatocytes.
2001 Mar 5
In vitro bacterial penetration of endodontically treated teeth coronally sealed with a dentin bonding agent.
2001 May
Community of male Euglossini bees (Hymenoptera: Apidae) in a secondary forest, Alcântara, MA, Brazil.
2001 Nov
Glycosides and xanthine oxidase inhibitors from Conyza bonariensis.
2001 Oct
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
Effect of three root canal sealers on the retentive strength of endodontic posts luted with a resin cement.
2002 Apr
Aerosolized essential oils and individual natural product compounds as brown treesnake repellents.
2002 Aug
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
Inhibition of human low density lipoprotein oxidation by active principles from spices.
2002 Jan
Chemosensory input and lateralization of brain function in the domestic chick.
2002 Jul 18
Effect of dowel space preparation and composite cement thickness on retention of a prefabricated dowel.
2002 Mar
In vitro antifungal activity of several antimicrobial compounds against Penicillium expansum.
2002 May
Molecular cloning and characterisation of three new ATP-binding cassette transporter genes from the wheat pathogen Mycosphaerella graminicola.
2002 May 1
Transcriptional control of monolignol biosynthesis in Pinus taeda: factors affecting monolignol ratios and carbon allocation in phenylpropanoid metabolism.
2002 May 24
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
401
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 Fri Dec 16 15:54:32 UTC 2022
Edited
by admin
on Fri Dec 16 15:54:32 UTC 2022
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 16 15:54:32 UTC 2022 , Edited by admin on Fri Dec 16 15:54:32 UTC 2022
DSLD 2902 (Number of products:13)
Created by admin on Fri Dec 16 15:54:32 UTC 2022 , Edited by admin on Fri Dec 16 15:54:32 UTC 2022
NCI_THESAURUS C245
Created by admin on Fri Dec 16 15:54:32 UTC 2022 , Edited by admin on Fri Dec 16 15:54:32 UTC 2022
JECFA EVALUATION EUGENOL
Created by admin on Fri Dec 16 15:54:32 UTC 2022 , Edited by admin on Fri Dec 16 15:54:32 UTC 2022
NDF-RT N0000185508
Created by admin on Fri Dec 16 15:54:32 UTC 2022 , Edited by admin on Fri Dec 16 15:54:32 UTC 2022
EPA PESTICIDE CODE 102701
Created by admin on Fri Dec 16 15:54:32 UTC 2022 , Edited by admin on Fri Dec 16 15:54:32 UTC 2022
Code System Code Type Description
ALANWOOD
eugenol
Created by admin on Fri Dec 16 15:54:32 UTC 2022 , Edited by admin on Fri Dec 16 15:54:32 UTC 2022
PRIMARY
EPA CompTox
DTXSID9020617
Created by admin on Fri Dec 16 15:54:32 UTC 2022 , Edited by admin on Fri Dec 16 15:54:32 UTC 2022
PRIMARY
RXCUI
4186
Created by admin on Fri Dec 16 15:54:32 UTC 2022 , Edited by admin on Fri Dec 16 15:54:32 UTC 2022
PRIMARY RxNorm
NDF-RT
N0000175629
Created by admin on Fri Dec 16 15:54:32 UTC 2022 , Edited by admin on Fri Dec 16 15:54:32 UTC 2022
PRIMARY Increased Histamine Release [PE]
CHEBI
4917
Created by admin on Fri Dec 16 15:54:32 UTC 2022 , Edited by admin on Fri Dec 16 15:54:32 UTC 2022
PRIMARY
CAS
97-53-0
Created by admin on Fri Dec 16 15:54:32 UTC 2022 , Edited by admin on Fri Dec 16 15:54:32 UTC 2022
PRIMARY
HSDB
210
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PRIMARY
DRUG BANK
DB09086
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PRIMARY
ECHA (EC/EINECS)
202-589-1
Created by admin on Fri Dec 16 15:54:32 UTC 2022 , Edited by admin on Fri Dec 16 15:54:32 UTC 2022
PRIMARY
NDF-RT
N0000184306
Created by admin on Fri Dec 16 15:54:32 UTC 2022 , Edited by admin on Fri Dec 16 15:54:32 UTC 2022
PRIMARY Cell-mediated Immunity [PE]
DAILYMED
3T8H1794QW
Created by admin on Fri Dec 16 15:54:32 UTC 2022 , Edited by admin on Fri Dec 16 15:54:32 UTC 2022
PRIMARY
PUBCHEM
3314
Created by admin on Fri Dec 16 15:54:32 UTC 2022 , Edited by admin on Fri Dec 16 15:54:32 UTC 2022
PRIMARY
NSC
209525
Created by admin on Fri Dec 16 15:54:32 UTC 2022 , Edited by admin on Fri Dec 16 15:54:32 UTC 2022
PRIMARY
MESH
D005054
Created by admin on Fri Dec 16 15:54:32 UTC 2022 , Edited by admin on Fri Dec 16 15:54:32 UTC 2022
PRIMARY
DRUG CENTRAL
4648
Created by admin on Fri Dec 16 15:54:32 UTC 2022 , Edited by admin on Fri Dec 16 15:54:32 UTC 2022
PRIMARY
RS_ITEM_NUM
1268965
Created by admin on Fri Dec 16 15:54:32 UTC 2022 , Edited by admin on Fri Dec 16 15:54:32 UTC 2022
PRIMARY
NSC
8895
Created by admin on Fri Dec 16 15:54:32 UTC 2022 , Edited by admin on Fri Dec 16 15:54:32 UTC 2022
PRIMARY
FDA UNII
3T8H1794QW
Created by admin on Fri Dec 16 15:54:32 UTC 2022 , Edited by admin on Fri Dec 16 15:54:32 UTC 2022
PRIMARY
EVMPD
SUB13776MIG
Created by admin on Fri Dec 16 15:54:32 UTC 2022 , Edited by admin on Fri Dec 16 15:54:32 UTC 2022
PRIMARY
ChEMBL
CHEMBL42710
Created by admin on Fri Dec 16 15:54:32 UTC 2022 , Edited by admin on Fri Dec 16 15:54:32 UTC 2022
PRIMARY
MERCK INDEX
M5210
Created by admin on Fri Dec 16 15:54:32 UTC 2022 , Edited by admin on Fri Dec 16 15:54:32 UTC 2022
PRIMARY Merck Index
NCI_THESAURUS
C75095
Created by admin on Fri Dec 16 15:54:32 UTC 2022 , Edited by admin on Fri Dec 16 15:54:32 UTC 2022
PRIMARY
NDF-RT
N0000171131
Created by admin on Fri Dec 16 15:54:32 UTC 2022 , Edited by admin on Fri Dec 16 15:54:32 UTC 2022
PRIMARY Allergens [Chemical/Ingredient]
WIKIPEDIA
EUGENOL
Created by admin on Fri Dec 16 15:54:32 UTC 2022 , Edited by admin on Fri Dec 16 15:54:32 UTC 2022
PRIMARY
Related Record Type Details
CHINESE CINNAMON LEAF OIL
PARENT -> CONSTITUENT MAY BE PRESENT
CINNAMON BARK OIL
PARENT -> CONSTITUENT MAY BE PRESENT
ASSAY (GC)
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.
CLOVE OIL
PARENT -> CONSTITUENT ALWAYS PRESENT
ASSAY (GC)
CINNAMON LEAF OIL
PARENT -> CONSTITUENT ALWAYS PRESENT
ASSAY (GC)
GEUM URBANUM WHOLE
PARENT -> CONSTITUENT ALWAYS PRESENT
CINNAMON
PARENT -> CONSTITUENT ALWAYS PRESENT
HOLY BASIL LEAF
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
CHINESE CINNAMON
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
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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