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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

Junge, C.
3
Sources: DOI: 10.1002/cber.189102402113Riechstoff ind. Volume 7, Pages 112, Journal, 1932

Approval Year

1994
149
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
Inhibitor
8297
Activator
1430
Activator
1430
Activator
1430
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
Approved
8429
TRUE Test

Approved Use

Unknown
Diagnostic
Approved
8429
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
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
Study of 202 natural, synthetic, and environmental chemicals for binding to the androgen receptor.
2003 Oct
An odorant derivative as an antagonist for an olfactory receptor.
2004 Nov
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.
2006 Nov
Impact of the arylhydrocarbon receptor on eugenol- and isoeugenol-induced cell cycle arrest in human immortalized keratinocytes (HaCaT).
2006 Sep
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
Chemicals with weak skin sensitizing properties can be identified using low-density microarrays on immature dendritic cells.
2007 Nov 1
Suppression of interleukin-2 gene expression by isoeugenol is mediated through down-regulation of NF-AT and NF-kappaB.
2007 Sep
Keratinocyte gene expression profiles discriminate sensitizing and irritating compounds.
2010 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
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
An in vitro test to screen skin sensitizers using a stable THP-1-derived IL-8 reporter cell line, THP-G8.
2011 Dec
The mouse eugenol odorant receptor: structural and functional plasticity of a broadly tuned odorant binding pocket.
2011 Feb 8
Impact of eugenol and isoeugenol on AhR translocation, target gene expression, and proliferation in human HaCaT keratinocytes.
2012
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
Development of a new in vitro skin sensitization assay (Epidermal Sensitization Assay; EpiSensA) using reconstructed human epidermis.
2013 Dec
Differentiation of skin sensitizers from irritant chemicals by interleukin-1α and macrophage inflammatory protein-2 in murine keratinocytes.
2013 Jan 10
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

Patents

DE1936727
3
JP2004018470A
3
JPH02196718A
8
JPH03234797A
4
JPH03263481A
4
JPH05139907A
6
JPH05236972A
4
JPH07165547A
4
JPS59175423A
5
JPS61171758A
5
JPS6372654A
5

Sample Use Guides

In Vivo Use Guide
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
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 GMT 2023
Edited
by admin
on Fri Dec 15 15:00:38 GMT 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 GMT 2023 , Edited by admin on Fri Dec 15 15:00:38 GMT 2023
PRIMARY
ECHA (EC/EINECS)
227-678-2
Created by admin on Fri Dec 15 15:00:38 GMT 2023 , Edited by admin on Fri Dec 15 15:00:38 GMT 2023
PRIMARY
EPA CompTox
DTXSID50872350
Created by admin on Fri Dec 15 15:00:38 GMT 2023 , Edited by admin on Fri Dec 15 15:00:38 GMT 2023
PRIMARY
CAS
5932-68-3
Created by admin on Fri Dec 15 15:00:38 GMT 2023 , Edited by admin on Fri Dec 15 15:00:38 GMT 2023
PRIMARY
FDA UNII
28FSR1NAY4
Created by admin on Fri Dec 15 15:00:38 GMT 2023 , Edited by admin on Fri Dec 15 15:00:38 GMT 2023
PRIMARY
CHEBI
50545
Created by admin on Fri Dec 15 15:00:38 GMT 2023 , Edited by admin on Fri Dec 15 15:00:38 GMT 2023
PRIMARY
PUBCHEM
853433
Created by admin on Fri Dec 15 15:00:38 GMT 2023 , Edited by admin on Fri Dec 15 15:00:38 GMT 2023
PRIMARY
MERCK INDEX
m6486
Created by admin on Fri Dec 15 15:00:38 GMT 2023 , Edited by admin on Fri Dec 15 15:00:38 GMT 2023
PRIMARY Merck Index
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