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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
Structure of ISOEUGENOL, (E)-

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+

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 1
Optical Activity NONE

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
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
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
Isoeugenol suppression of inducible nitric oxide synthase expression is mediated by down-regulation of NF-kappaB, ERK1/2, and p38 kinase.
2007 Dec 8
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
A new in vitro method for identifying chemical sensitizers combining peptide binding with ARE/EpRE-mediated gene expression in human skin cells.
2010 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
Active transport of contact allergens in human monocyte-derived dendritic cells is mediated by multidrug resistance related proteins.
2011 Apr 15
The mouse eugenol odorant receptor: structural and functional plasticity of a broadly tuned odorant binding pocket.
2011 Feb 8
Isoeugenol destabilizes IL-8 mRNA expression in THP-1 cells through induction of the negative regulator of mRNA stability tristetraprolin.
2012 Feb
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
NCTC 2544 and IL-18 production: a tool for the identification of contact allergens.
2013 Apr
Differentiation of skin sensitizers from irritant chemicals by interleukin-1α and macrophage inflammatory protein-2 in murine keratinocytes.
2013 Jan 10
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:00:38 UTC 2023
Edited
by admin
on Fri Dec 15 15:00:38 UTC 2023
Record UNII
28FSR1NAY4
Record Status Validated (UNII)
Record Version
  • Download
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
NSC
209522
Created by admin on Fri Dec 15 15:00:38 UTC 2023 , Edited by admin on Fri Dec 15 15:00:38 UTC 2023
PRIMARY
ECHA (EC/EINECS)
227-678-2
Created by admin on Fri Dec 15 15:00:38 UTC 2023 , Edited by admin on Fri Dec 15 15:00:38 UTC 2023
PRIMARY
EPA CompTox
DTXSID50872350
Created by admin on Fri Dec 15 15:00:38 UTC 2023 , Edited by admin on Fri Dec 15 15:00:38 UTC 2023
PRIMARY
CAS
5932-68-3
Created by admin on Fri Dec 15 15:00:38 UTC 2023 , Edited by admin on Fri Dec 15 15:00:38 UTC 2023
PRIMARY
FDA UNII
28FSR1NAY4
Created by admin on Fri Dec 15 15:00:38 UTC 2023 , Edited by admin on Fri Dec 15 15:00:38 UTC 2023
PRIMARY
CHEBI
50545
Created by admin on Fri Dec 15 15:00:38 UTC 2023 , Edited by admin on Fri Dec 15 15:00:38 UTC 2023
PRIMARY
PUBCHEM
853433
Created by admin on Fri Dec 15 15:00:38 UTC 2023 , Edited by admin on Fri Dec 15 15:00:38 UTC 2023
PRIMARY
MERCK INDEX
m6486
Created by admin on Fri Dec 15 15:00:38 UTC 2023 , Edited by admin on Fri Dec 15 15:00:38 UTC 2023
PRIMARY Merck Index