METHYLISOTHIAZOLINONE

Possibly Marketed Outside US

Details

Stereochemistry	ACHIRAL
Molecular Formula	C4H5NOS
Molecular Weight	115.154
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1SC=CC1=O

InChI

InChIKey=BEGLCMHJXHIJLR-UHFFFAOYSA-N

InChI=1S/C4H5NOS/c1-5-4(6)2-3-7-5/h2-3H,1H3

HIDE SMILES / InChI

Molecular Formula	C4H5NOS
Molecular Weight	115.154
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.biosave.com/products/2-methyl-4-isothiazolin-3-one-hydrochloride-159692 | https://www.sigmaaldrich.com/catalog/product/sigma/m6045 | https://www.ncbi.nlm.nih.gov/pubmed/30697834 | https://www.ncbi.nlm.nih.gov/pubmed/30426516

2-Methyl-4-isothiazolin-3-one hydrochloride is an isothiazolinone based biocide and preservative used in personal care products. 2-Methyl-4-isothiazolin-3-one is also used for controlling microbial growth in water-containing solution. It is used to study the effects of tyrosine phosphorylation on focal adhesion kinase (FAK) activity in the development of neural axons and dendrites. 2-Methyl-4-isothiazolin-3-one hydrochloride (Methylisothiazolinone hydrochloride) is a common preservative used in industrial products, owing to its strong biocide effect. Contact allergy to Methylisothiazolinone hydrochloride has been reported in different occupations, including mechanics, hairdressers and healthcare workers.

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Preservative 2 Sources: http://www.biosave.com/products/2-methyl-4-isothiazolin-3-one-hydrochloride-159692

PubMed

Title	Date	PubMed
In vitro induction of apoptosis vs. necrosis by widely used preservatives: 2-phenoxyethanol, a mixture of isothiazolinones, imidazolidinyl urea and 1,2-pentanediol.	2002 Feb 1	11853695
Methylisothiazolinones elicit increased production of both T helper (Th)1- and Th2-like cytokines by peripheral blood mononuclear cells from contact allergic individuals.	2003 Dec	14674894
Patch test sensitization to methylchloroisothiazolinone + methylisothiazolinone and 4,4'-diaminodiphenylmethane.	2003 Jan	12641579
Studies of chemical selectivity of hapten, reactivity, and skin sensitization potency. 3. Synthesis and studies on the reactivity toward model nucleophiles of the 13C-labeled skin sensitizers, 5-chloro-2-methylisothiazol-3-one (MCI) and 2-methylisothiazol-3-one (MI).	2003 May	12755592
Contact sensitization to 5-chloro-2-methyl-4-isothiazolin-3-one and 2-methyl-4-isothiazolin-3-one in children.	2003 Oct	14996074
Co-existing sensitivity to metronidazole and isothiazolinone.	2003 Sep	12950340
[Allergy to cosmetics. II. Preservatives].	2004	15493505
Separation of preservatives in cosmetic products by micellar electrokinetic chromatography.	2004 Dec	15636528
Covalent binding of the 13C-labeled skin sensitizers 5-chloro-2-methylisothiazol-3-one (MCI) and 2-methylisothiazol-3-one (MI) to a model peptide and glutathione.	2004 Jan 19	14698160
From experiment to theory: molecular orbital parameters to interpret the skin sensitization potential of 5-chloro-2-methylisothiazol-3-one and 2-methylisothiazol-3-one.	2005 Feb	15720139
GSH depletion, protein S-glutathionylation and mitochondrial transmembrane potential hyperpolarization are early events in initiation of cell death induced by a mixture of isothiazolinones in HL60 cells.	2006 Feb	16458373
Contact dermatitis from methylisothiazolinone in a paint factory.	2006 Jun	16787453
Methylisothiazolinone, a neurotoxic biocide, disrupts the association of SRC family tyrosine kinases with focal adhesion kinase in developing cortical neurons.	2006 Jun	16547166
Preservatives sensitivity in Israel: a 10-year overview (1995-2004).	2006 Oct	16958921
'Dermatologically tested' baby toilet tissues: a cause of allergic contact dermatitis in adults.	2007 Aug	17627648
Antifungal activities of bronopol and 2-methyl-4-isothiazolin-3-one (MT) against saprolegnia.	2007 Dec	18198720
Analysis of isothiazolinones in environmental waters by gas chromatography-mass spectrometry.	2007 Sep 14	17681349
Quantitative relationships between patch test reactivity and use test reactivity: an overview.	2008	18988092
The impact of meteorological conditions on patch test results with 12 standard series allergens (fragrances, biocides, topical ingredients).	2008 Apr	18284398
Structure-activity relationships for the impact of selected isothiazol-3-one biocides on glutathione metabolism and glutathione reductase of the human liver cell line Hep G2.	2008 Apr 18	18313196
Alkalization of wall paint prevents airborne contact dermatitis in patients with sensitization to isothiazolinones.	2008 Aug	18759890
Cross-reactivity between methylchloroisothiazolinone/methylisothiazolinone, methylisothiazolinone, and other isothiazolinones in workers at a plant producing binders for paints and glues.	2008 Jan	18154567
Disruption of FAK signaling: a side mechanism in cytotoxicity.	2008 Mar 12	18215454
Analysis of allergens in metalworking fluids.	2008 Nov	18976375
[Facial allergic contact dermatitis. Data from the IVDK and review of literature].	2009 Jan	19099269
[Allergic contact dermatitis to cosmetics].	2009 Jan-Feb	19268112
Identifying the optimal patch test concentration for methylchloroisothiazolinone and methylisothiazolinone.	2009 May	19397621
Methylisothiazolinone, an emerging allergen in cosmetics?	2010 Aug	20629674
Analysis of isothiazolinone biocides in paper for food packaging by ultra-high-performance liquid chromatography-tandem mass spectrometry.	2010 Dec	20960358
Concomitant contact allergy to methylchloroisothiazolinone/methylisothiazolinone and formaldehyde-releasing preservatives.	2010 Jan	20136882
Final report of the safety assessment of methylisothiazolinone.	2010 Jul	20634507
Methylchloroisothiazolinone / methylisothiazolinone and moist wipe dermatitis.	2010 May 15	20492831
Moist toilet paper: allergy to the nonhalogenated derivative methylisothiazolinone preservative alone.	2010 Oct	20956669
Prevalence and cause of methylisothiazolinone contact allergy.	2010 Sep	20690940
Methylisothiazolinone: dermal and respiratory immune responses in mice.	2015 Jun 15	25907379
Chemical allergens stimulate human epidermal keratinocytes to produce lymphangiogenic vascular endothelial growth factor.	2015 Mar 1	25617811
Effect of cosmetic chemical preservatives on resident flora isolated from healthy facial skin.	2019 Apr	30548758
Methylchloroisothiazolinone and/or methylisothiazolinone in cosmetic products-A market survey.	2019 Feb	30426516
Contact allergy to methylchloroisothiazolinone/methylisothiazolinone in north-eastern Italy: a temporal trend from 1996 to 2016.	2019 May	30697834

Patents

Sample Use Guides

In Vitro Use Guide

Methylisothiazolinone (150 uM) was able to trigger the three main key events (KE1, KE2, and KE3) of the sensitization phase of ACD in THP-1 cells.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:28:18 UTC 2023` Edited by `admin` on `Fri Dec 15 15:28:18 UTC 2023`
Record UNII	229D0E1QFA
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

METHYLISOTHIAZOLINONE

Official Name

English

METHYLISOTHIAZOLINONE [INCI]

Common Name

English

2-METHYL-3(2H)-ISOTHIAZOLONE

Systematic Name

English

METHYLISOTHIAZOLINONE [MART.]

Common Name

English

METHYLISOTHIAZOLINONE [II]

Common Name

English

METHYLISOTHIAZOLINONE [MI]

Common Name

English

METHYLISOTHIAZOLINONE [VANDF]

Common Name

English

2-METHYL-4-ISOTHIAZOLIN-3-ONE

Systematic Name

English

MIT

Common Name

English

Classification Tree Code System Code

EPA PESTICIDE CODE

107104