ISOEUGENOL

US Approved Allergenic Extract (1994)

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
Liquid chromatographic separation and fluorometric determination of cis- and trans-isoeugenol in perfumes, colognes, and toilet waters.	1988 Jul-Aug	3417607
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	10871845
Study of 202 natural, synthetic, and environmental chemicals for binding to the androgen receptor.	2003 Oct	14565775
An odorant derivative as an antagonist for an olfactory receptor.	2004 Nov	15574817
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
Isoeugenol suppression of inducible nitric oxide synthase expression is mediated by down-regulation of NF-kappaB, ERK1/2, and p38 kinase.	2007 Dec 8	17698059
Do anesthetics and sampling strategies affect transcription analysis of fish tissues?	2007 Jun 8	17559653
Chemicals with weak skin sensitizing properties can be identified using low-density microarrays on immature dendritic cells.	2007 Nov 1	17936526
Suppression of interleukin-2 gene expression by isoeugenol is mediated through down-regulation of NF-AT and NF-kappaB.	2007 Sep	17630204
Active transport of contact allergens in human monocyte-derived dendritic cells is mediated by multidrug resistance related proteins.	2011 Apr 15	21284934
The mouse eugenol odorant receptor: structural and functional plasticity of a broadly tuned odorant binding pocket.	2011 Feb 8	21142015
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
Development of a new in vitro skin sensitization assay (Epidermal Sensitization Assay; EpiSensA) using reconstructed human epidermis.	2013 Dec	23999411
Differentiation of skin sensitizers from irritant chemicals by interleukin-1α and macrophage inflammatory protein-2 in murine keratinocytes.	2013 Jan 10	23178550
Development of an in vitro dendritic cell-based test for skin sensitizer identification.	2013 Mar 18	23445166
Antifungal efficacy of some natural phenolic compounds against significant pathogenic and toxinogenic filamentous fungi.	2013 Oct	23800587
In vitro activity of natural phenolic compounds against fluconazole-resistant Candida species: a quantitative structure-activity relationship analysis.	2014 Apr	24387763
Chemical allergens stimulate human epidermal keratinocytes to produce lymphangiogenic vascular endothelial growth factor.	2015 Mar 1	25617811

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	Mixture Created by `admin` on `Fri Dec 15 17:40:32 UTC 2023` Edited by `admin` on `Fri Dec 15 17:40:32 UTC 2023`
Record UNII	5M0MWY797U
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ISOEUGENOL

Official Name

English

ISOEUGENOL [FHFI]

Common Name

English

4-HYDROXY-3-METHOXY-1-PROPENYLBENZENE

Common Name

English

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

Common Name

English

2-METHOXY-4-PROPENYLPHENOL

Common Name

English

ISOEUGENOL [FCC]

Common Name

English

FEMA NO. 2468

Code

English

ISOEUGENOL [INCI]

Common Name

English

ISOEUGENOL [USP-RS]

Common Name

English

ISOEUGENOL [MI]

Common Name

English

NSC-6769

Code

English

4-PROPENYLGUAIACOL

Common Name

English

Classification Tree Code System Code

WHO-VATC

QN01AX94