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 |
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Target ID: GO:1903409 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12126794 |
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Target ID: CHEMBL4794 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14514756 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | DENTEK EUGENOL Approved UseFor the temporary relief of throbbing, persistent toothache due to cavity. |
PubMed
Title | Date | PubMed |
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Effects of isoeugenol on oxidative stress pathways in normal and streptozotocin-induced diabetic rats. | 2001 |
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Evaluation of volatile chemical treatments for lethality to Salmonella on alfalfa seeds and sprouts. | 2001 Apr |
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Anthelmintic activity of essential oil of Ocimum sanctum and eugenol. | 2001 Aug |
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Suppression of chemical mutagen-induced SOS response by alkylphenols from clove (Syzygium aromaticum) in the Salmonella typhimurium TA1535/pSK1002 umu test. | 2001 Aug |
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Langerhans cells and immature dendritic cells as model systems for screening of skin sensitizers. | 2001 Aug-Oct |
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The effect of various root canal sealers on India ink and different concentrations of methylene blue solutions. | 2001 Dec |
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Measurement of urinary methoxyphenols and their use for biological monitoring of wood smoke exposure. | 2001 Feb |
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Inhibitory effects of eugenol and thymol on Penicillium citrinum strains in culture media and cheese. | 2001 Jul 20 |
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Formaldehyde release from ground root canal sealer in vitro. | 2001 Jun |
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Phytochemical constituents of Artemisia japonica ssp. littoricola. | 2001 Jun |
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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 |
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Contact allergy to balsam of Peru. II. Patch test results in 102 patients with selected balsam of Peru constituents. | 2001 Jun |
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Reactive oxygen species generation and photo-cytotoxicity of eugenol in solutions of various pH. | 2001 Jun |
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Structure-activity relationships for a large diverse set of natural, synthetic, and environmental estrogens. | 2001 Mar |
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Evaluation of the developmental toxicity of isoeugenol in Sprague-Dawley (CD) rats. | 2001 Mar |
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Root canal sealers cause cytotoxicity and oxidative damage in hepatocytes. | 2001 Mar 5 |
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In vitro bacterial penetration of endodontically treated teeth coronally sealed with a dentin bonding agent. | 2001 May |
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Community of male Euglossini bees (Hymenoptera: Apidae) in a secondary forest, Alcântara, MA, Brazil. | 2001 Nov |
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Glycosides and xanthine oxidase inhibitors from Conyza bonariensis. | 2001 Oct |
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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 |
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Effect of three root canal sealers on the retentive strength of endodontic posts luted with a resin cement. | 2002 Apr |
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Aerosolized essential oils and individual natural product compounds as brown treesnake repellents. | 2002 Aug |
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Inducing the cell cycle arrest and apoptosis of oral KB carcinoma cells by hydroxychavicol: roles of glutathione and reactive oxygen species. | 2002 Feb |
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The effects of eugenol and epoxy-resin on the strength of a hybrid composite resin. | 2002 Feb |
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Inhibition of human low density lipoprotein oxidation by active principles from spices. | 2002 Jan |
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Chemosensory input and lateralization of brain function in the domestic chick. | 2002 Jul 18 |
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Effect of dowel space preparation and composite cement thickness on retention of a prefabricated dowel. | 2002 Mar |
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In vitro antifungal activity of several antimicrobial compounds against Penicillium expansum. | 2002 May |
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Molecular cloning and characterisation of three new ATP-binding cassette transporter genes from the wheat pathogen Mycosphaerella graminicola. | 2002 May 1 |
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Transcriptional control of monolignol biosynthesis in Pinus taeda: factors affecting monolignol ratios and carbon allocation in phenylpropanoid metabolism. | 2002 May 24 |
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
Fri Dec 16 15:54:32 UTC 2022
by
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on
Fri Dec 16 15:54:32 UTC 2022
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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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eugenol
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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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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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3314
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209525
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D005054
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4648
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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 MAY BE PRESENT |
ASSAY (GC)
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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 ALWAYS PRESENT |
ASSAY (GC)
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PARENT -> CONSTITUENT ALWAYS PRESENT |
ASSAY (GC)
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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 |
USP
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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 |