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: https://www.ncbi.nlm.nih.gov/pubmed/15606655http://www.ema.europa.eu/docs/en_GB/document_library/Maximum_Residue_Limits_-_Report/2011/05/WC500106362.pdfCurator's Comment: description was created based on several sources, including:
http://www.umces.edu/sites/default/files/pdfs/oraa/guidance_for_industry.pdf
https://www.acs.org/content/acs/en/molecule-of-the-week/archive/i/isoeugenol.html
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15606655http://www.ema.europa.eu/docs/en_GB/document_library/Maximum_Residue_Limits_-_Report/2011/05/WC500106362.pdf
Curator's Comment: description was created based on several sources, including:
http://www.umces.edu/sites/default/files/pdfs/oraa/guidance_for_industry.pdf
https://www.acs.org/content/acs/en/molecule-of-the-week/archive/i/isoeugenol.html
Clove oil is a natural product, derived from the Eugenia caryophyllata tree. Clove oil is 85 to 95% eugenol. Isoeugenol and methyleugenol make up 5 to 15% of the remaining ingredients. Isoeugenol is manufactured from eugenol by a process of isomerization. Isoeugenol have been used in foods and eugenol has been used in animal feeds. Isoeugenol is used as a fish anesthetic. The mechanism of action of isoeugenol in fish has not been determined. It is hypothesised that its effects are mediated via receptors controlling cellular ion channels in a similar way to that described for local anaesthetics. Reports of adverse reactions involving the use of isoeugenol in humans are primarily confined to incidents of contact sensitization or allergy following dermal exposure.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL3816 |
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Target ID: CHEMBL2169736 |
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Target ID: CHEMBL2231 |
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Target ID: CHEMBL6007 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| 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 |
|---|---|---|
| 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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| An odorant derivative as an antagonist for an olfactory receptor. | 2004 Nov |
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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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| Impact of the arylhydrocarbon receptor on eugenol- and isoeugenol-induced cell cycle arrest in human immortalized keratinocytes (HaCaT). | 2006 Sep |
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| Isoeugenol suppression of inducible nitric oxide synthase expression is mediated by down-regulation of NF-kappaB, ERK1/2, and p38 kinase. | 2007 Dec 8 |
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| Do anesthetics and sampling strategies affect transcription analysis of fish tissues? | 2007 Jun 8 |
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| Chemicals with weak skin sensitizing properties can be identified using low-density microarrays on immature dendritic cells. | 2007 Nov 1 |
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| Suppression of interleukin-2 gene expression by isoeugenol is mediated through down-regulation of NF-AT and NF-kappaB. | 2007 Sep |
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| Keratinocyte gene expression profiles discriminate sensitizing and irritating compounds. | 2010 Sep |
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| A new in vitro method for identifying chemical sensitizers combining peptide binding with ARE/EpRE-mediated gene expression in human skin cells. | 2010 Sep |
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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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| Active transport of contact allergens in human monocyte-derived dendritic cells is mediated by multidrug resistance related proteins. | 2011 Apr 15 |
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| An in vitro test to screen skin sensitizers using a stable THP-1-derived IL-8 reporter cell line, THP-G8. | 2011 Dec |
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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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| Impact of eugenol and isoeugenol on AhR translocation, target gene expression, and proliferation in human HaCaT keratinocytes. | 2012 |
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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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| B cell increases and ex vivo IL-2 production as secondary endpoints for the detection of sensitizers in non-radioisotopic local lymph node assay using flow cytometry. | 2012 Mar 25 |
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| NCTC 2544 and IL-18 production: a tool for the identification of contact allergens. | 2013 Apr |
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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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| Differentiation of skin sensitizers from irritant chemicals by interleukin-1α and macrophage inflammatory protein-2 in murine keratinocytes. | 2013 Jan 10 |
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| Development of an in vitro dendritic cell-based test for skin sensitizer identification. | 2013 Mar 18 |
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| Antifungal efficacy of some natural phenolic compounds against significant pathogenic and toxinogenic filamentous fungi. | 2013 Oct |
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| In vitro activity of natural phenolic compounds against fluconazole-resistant Candida species: a quantitative structure-activity relationship analysis. | 2014 Apr |
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| Chemical allergens stimulate human epidermal keratinocytes to produce lymphangiogenic vascular endothelial growth factor. | 2015 Mar 1 |
Sample Use Guides
Subjects were investigated by closed patch test using 8mm Finn Chambers1 on Scanpor1 tape (Epitest, Tuusula, Finland) dosed with (E)-Isoeugenol (1.0% pet.) Chambers were removed after 2 days. Reactions were read on 2 occasions over 5 days.
Route of Administration:
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50545
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M6486
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PRIMARY | Merck Index |
SUBSTANCE RECORD
