Details
Stereochemistry | ACHIRAL |
Molecular Formula | C10H12O2 |
Molecular Weight | 164.2011 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC(\C=C\C)=CC=C1O
InChI
InChIKey=BJIOGJUNALELMI-ONEGZZNKSA-N
InChI=1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3-7,11H,1-2H3/b4-3+
DescriptionSources: http://www.ema.europa.eu/docs/en_GB/document_library/Maximum_Residue_Limits_-_Report/2011/05/WC500106362.pdfhttps://www.ncbi.nlm.nih.gov/pubmed/15606655Curator's Comment: description was created based on several sources, including
https://link.springer.com/article/10.1007/s00044-015-1486-6 | https://ntp.niehs.nih.gov/ntp/htdocs/chem_background/exsumpdf/isoeugenol_508.pdf | https://www.ncbi.nlm.nih.gov/pubmed/21995306
Sources: http://www.ema.europa.eu/docs/en_GB/document_library/Maximum_Residue_Limits_-_Report/2011/05/WC500106362.pdfhttps://www.ncbi.nlm.nih.gov/pubmed/15606655
Curator's Comment: description was created based on several sources, including
https://link.springer.com/article/10.1007/s00044-015-1486-6 | https://ntp.niehs.nih.gov/ntp/htdocs/chem_background/exsumpdf/isoeugenol_508.pdf | https://www.ncbi.nlm.nih.gov/pubmed/21995306
(E)-Isoeugenol is crystalline while compound with spice clove type odor. The melting point of E-isoeugenol is 33°C. E-Isoeugenol has been shown to cause contact and allergic dermatitis in humans. Positive skin patch tests in numerous individuals have confirmed the sensitizing ability of isoeugenol.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL3816 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21995306 |
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Target ID: CHEMBL2169736 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27220325 |
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Target ID: CHEMBL2231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22686307 |
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Target ID: 57491.0 Gene Symbol: AHRR Sources: https://www.ncbi.nlm.nih.gov/pubmed/22686307 |
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Target ID: CHEMBL6007 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18456404 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Diagnostic | TRUE Test Approved UseUnknown |
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Diagnostic | TRUE Test Approved UseFragrance mix is composed of eight substances, including isoeugenol (approximately 15 ug). |
PubMed
Title | Date | PubMed |
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Liquid chromatographic separation and fluorometric determination of cis- and trans-isoeugenol in perfumes, colognes, and toilet waters. | 1988 Jul-Aug |
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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 |
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Structure-activity relationships for a large diverse set of natural, synthetic, and environmental estrogens. | 2001 Mar |
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Study of 202 natural, synthetic, and environmental chemicals for binding to the androgen receptor. | 2003 Oct |
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Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods. | 2006 Nov |
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Do anesthetics and sampling strategies affect transcription analysis of fish tissues? | 2007 Jun 8 |
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Identification of PDL-1 as a novel biomarker of sensitizer exposure in dendritic-like cells. | 2010 Sep |
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The intra- and inter-laboratory reproducibility and predictivity of the KeratinoSens assay to predict skin sensitizers in vitro: results of a ring-study in five laboratories. | 2011 Apr |
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The mouse eugenol odorant receptor: structural and functional plasticity of a broadly tuned odorant binding pocket. | 2011 Feb 8 |
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Isoeugenol destabilizes IL-8 mRNA expression in THP-1 cells through induction of the negative regulator of mRNA stability tristetraprolin. | 2012 Feb |
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Development of a new in vitro skin sensitization assay (Epidermal Sensitization Assay; EpiSensA) using reconstructed human epidermis. | 2013 Dec |
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Antifungal efficacy of some natural phenolic compounds against significant pathogenic and toxinogenic filamentous fungi. | 2013 Oct |
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Chemical allergens stimulate human epidermal keratinocytes to produce lymphangiogenic vascular endothelial growth factor. | 2015 Mar 1 |
Sample Use Guides
Isoeugenol is effective at low concentrations of 10 to 20 mg/L corresponding to active ingredient concentrations of 5 to 10 mg/L.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12828253
Isoeugenol in low concentrations 206 uM caused a distinct decrease in twitch response in phrenic nerve-diaphragm preparations.
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m6486
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PRIMARY | Merck Index |
SUBSTANCE RECORD