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Details

Stereochemistry ACHIRAL
Molecular Formula C10H12O2
Molecular Weight 164.2015
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of ISOEUGENOL, (E)-

SMILES

C/C(/[H])=C(\[H])/c1ccc(c(c1)OC)O

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+

HIDE SMILES / InChI

Description
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.

Originator

Sources: DOI: 10.1002/cber.189102402113Riechstoff ind. Volume 7, Pages 112, Journal, 1932

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
TRUE Test

Approved Use

Unknown
Diagnostic
TRUE Test

Approved Use

Fragrance mix is composed of eight substances, including isoeugenol (approximately 15 ug).
PubMed

PubMed

TitleDatePubMed
Liquid chromatographic separation and fluorometric determination of cis- and trans-isoeugenol in perfumes, colognes, and toilet waters.
1988 Jul-Aug
Structure-activity relationships for a large diverse set of natural, synthetic, and environmental estrogens.
2001 Mar
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.
2006 Nov
Do anesthetics and sampling strategies affect transcription analysis of fish tissues?
2007 Jun 8
Suppression of interleukin-2 gene expression by isoeugenol is mediated through down-regulation of NF-AT and NF-kappaB.
2007 Sep
Identification of PDL-1 as a novel biomarker of sensitizer exposure in dendritic-like cells.
2010 Sep
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
The mouse eugenol odorant receptor: structural and functional plasticity of a broadly tuned odorant binding pocket.
2011 Feb 8
Development of an in vitro dendritic cell-based test for skin sensitizer identification.
2013 Mar 18
Antifungal efficacy of some natural phenolic compounds against significant pathogenic and toxinogenic filamentous fungi.
2013 Oct
In vitro activity of natural phenolic compounds against fluconazole-resistant Candida species: a quantitative structure-activity relationship analysis.
2014 Apr
Chemical allergens stimulate human epidermal keratinocytes to produce lymphangiogenic vascular endothelial growth factor.
2015 Mar 1
Patents

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
Isoeugenol in low concentrations 206 uM caused a distinct decrease in twitch response in phrenic nerve-diaphragm preparations.
Name Type Language
ISOEUGENOL, (E)-
Systematic Name English
(E)-2-METHOXY-4-(1-PROPENYL)PHENOL
Systematic Name English
ISOEUGENOL TRANS-FORM
MI  
Common Name English
E-ISOEUGENOL
Systematic Name English
ISOEUGENOL, TRANS-
Systematic Name English
NSC-209522
Code English
ISOEUGENOL, E-
Systematic Name English
(E)-4-PROPENYLGUAIACOL
Systematic Name English
ISOEUGENOL TRANS-FORM [MI]
Common Name English
TRANS-ISOEUGENOL
Systematic Name English
Code System Code Type Description
ECHA (EC/EINECS)
227-678-2
Created by admin on Sat Jun 26 15:40:18 UTC 2021 , Edited by admin on Sat Jun 26 15:40:18 UTC 2021
PRIMARY
EPA CompTox
5932-68-3
Created by admin on Sat Jun 26 15:40:18 UTC 2021 , Edited by admin on Sat Jun 26 15:40:18 UTC 2021
PRIMARY
CAS
5932-68-3
Created by admin on Sat Jun 26 15:40:18 UTC 2021 , Edited by admin on Sat Jun 26 15:40:18 UTC 2021
PRIMARY
FDA UNII
28FSR1NAY4
Created by admin on Sat Jun 26 15:40:18 UTC 2021 , Edited by admin on Sat Jun 26 15:40:18 UTC 2021
PRIMARY
PUBCHEM
853433
Created by admin on Sat Jun 26 15:40:18 UTC 2021 , Edited by admin on Sat Jun 26 15:40:18 UTC 2021
PRIMARY
MERCK INDEX
M6486
Created by admin on Sat Jun 26 15:40:18 UTC 2021 , Edited by admin on Sat Jun 26 15:40:18 UTC 2021
PRIMARY Merck Index