ISOEUGENOL, (E)-

US Approved Allergenic Extract (1994)

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 Search

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
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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cytosolic phospholipase A2 7 Target ID: CHEMBL3816 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21995306	Inhibitor 8297
Tyrosyl-DNA phosphodiesterase 2 4 Target ID: CHEMBL2169736 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27220325	Inhibitor 8297
Cytochrome P450 1A1 31 Target ID: CHEMBL2231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22686307	Activator 1430
aryl-hydrocarbon receptor repressor 3 Target ID: 57491.0 Gene Symbol: AHRR Sources: https://www.ncbi.nlm.nih.gov/pubmed/22686307	Activator 1430
Transient receptor potential cation channel subfamily A member 1 38 Target ID: CHEMBL6007 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18456404	Activator 1430

Conditions

Condition	Modality	Targets	Highest Phase	Product
Allergic contact dermatitis 14 Sources: http://www.fda.gov/downloads/BiologicsBloodVaccines/Allergenics/UCM294327.pdf	Diagnostic		Approved 8429	TRUE Test Approved Use Unknown
Allergic contact dermatitis 14 Sources: http://www.fda.gov/downloads/BiologicsBloodVaccines/Allergenics/UCM294327.pdf	Diagnostic		Approved 8429	TRUE Test Approved Use Fragrance mix is composed of eight substances, including isoeugenol (approximately 15 ug).

PubMed

Title	Date	PubMed
Study of 202 natural, synthetic, and environmental chemicals for binding to the androgen receptor.	2003 Oct	14565775
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.	2006 Nov	16497524
Impact of the arylhydrocarbon receptor on eugenol- and isoeugenol-induced cell cycle arrest in human immortalized keratinocytes (HaCaT).	2006 Sep	16972787
Impact of eugenol and isoeugenol on AhR translocation, target gene expression, and proliferation in human HaCaT keratinocytes.	2012	22686307
NCTC 2544 and IL-18 production: a tool for the identification of contact allergens.	2013 Apr	23063874
In vitro activity of natural phenolic compounds against fluconazole-resistant Candida species: a quantitative structure-activity relationship analysis.	2014 Apr	24387763

Patents

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

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Name

Type

Language

ISOEUGENOL, (E)-

Systematic Name

English

(E)-2-METHOXY-4-(1-PROPENYL)PHENOL

Systematic Name

English

ISOEUGENOL TRANS-FORM

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