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Details

Stereochemistry ACHIRAL
Molecular Formula C4H10O2S
Molecular Weight 122.186
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of THIODIGLYCOL

SMILES

OCCSCCO

InChI

InChIKey=YODZTKMDCQEPHD-UHFFFAOYSA-N
InChI=1S/C4H10O2S/c5-1-3-7-4-2-6/h5-6H,1-4H2

HIDE SMILES / InChI

Molecular Formula C4H10O2S
Molecular Weight 122.186
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Thiodiglycol is the organosulfur structurally similar to diethylene glycol used as a solvent in a variety of applications ranging from dyeing textiles to inks in some ballpoint pens. In chemical synthesis, it is used as a building block for protection products, dispersants, fibers, plasticizers, rubber accelerators, pesticides, dyes, and various other organic chemicals. In the manufacture of polymers, it is used as a chain transfer agent. Thiodiglycol is a precursor in the production of Sulfur mustard and it is also considered as a “Schedule 2” compound (dual-use chemicals with low to moderate commercial use and high-risk precursors) within the terms of the Chemical Weapons Convention treaty.

Approval Year

Targets

Targets

PubMed

PubMed

TitleDatePubMed
Dithiothreitol causes HIV-1 integrase dimer dissociation while agents interacting with the integrase dimer interface promote dimer formation.
2011-03-15
Amino acid availability controls TRB3 transcription in liver through the GCN2/eIF2α/ATF4 pathway.
2010-12-21
New reagents for enhanced liquid chromatographic separation and charging of intact protein ions for electrospray ionization mass spectrometry.
2010-09-01
Point scanning confocal microscopy facilitates 3D human hair follicle imaging in tissue sections.
2010-07-01
Capsaicinoids, chloropicrin and sulfur mustard: possibilities for exposure biomarkers.
2010
Modified titania nanotubes for decontamination of sulphur mustard.
2009-08-15
Biodegradation of thiodiglycol, a hydrolyzate of the chemical weapon Yperite, by benzothiophene-desulfurizing bacteria.
2009-08-15
Microbial responses to mustard gas dumped in the Baltic Sea.
2009-08
Reactions of sulphur mustard and sarin on V 1.02 O 2.98 nanotubes.
2009-07-30
Comparison of metal-dependent catalysis by HIV-1 and ASV integrase proteins using a new and rapid, moderate throughput assay for joining activity in solution.
2009-06-29
Optimization of codon composition and regulatory elements for expression of human insulin like growth factor-1 in transgenic chloroplasts and evaluation of structural identity and function.
2009-04-03
Screening hydrolysis products of sulfur mustard agents by high-performance liquid chromatography with inductively coupled plasma mass spectrometry detection.
2009-04
New insights into the biodegradation of thiodiglycol, the hydrolysis product of Yperite (sulfur mustard gas).
2009-04
Kinetics of the degradation of sulfur mustard on ambient and moist concrete.
2009-02-15
Water-induced hydrophobicity of soy protein materials containing 2,2-diphenyl-2-hydroxyethanoic acid.
2008-09
Sulfur mustard research--strategies for the development of improved medical therapy.
2008-06-10
The effect of mustard gas on the biological activity of soil.
2008-03
Gas chromatographic-mass spectrometric analysis of sulfur mustard-plasma protein adducts: validation and use in a rat inhalation model.
2008-02-14
Improvements in the methodology of monitoring sulfur mustard exposure by gas chromatography-mass spectrometry analysis of cleaved and derivatized blood protein adducts.
2008-02-14
Analysis of urinary metabolites of sulfur mustard in two individuals after accidental exposure.
2008-02-14
Chronic health effects of sulphur mustard exposure with special reference to Iranian veterans.
2008
Sulfur mustard toxicity following dermal exposure: role of oxidative stress, and antioxidant therapy.
2007-10-30
Destruction of chemical agent simulants in a supercritical water oxidation bench-scale reactor.
2007-08-17
Soil bacterium Pseudomonas sp.: destroyer of mustard gas hydrolysis products.
2007-08
Developmental toxicity of thiodiglycol in Sprague-Dawley rats.
2007-07-31
Differential affinity of mammalian histone H1 somatic subtypes for DNA and chromatin.
2007-05-11
Analysis of the sulphur mustard metabolites thiodiglycol and thiodiglycol sulphoxide in urine using isotope-dilution gas chromatography-ion trap tandem mass spectrometry.
2007-01-01
2,2'-thiodiethanol: a new water soluble mounting medium for high resolution optical microscopy.
2007-01
Thiodiglycol, the hydrolysis product of sulfur mustard: analysis of in vitro biotransformation by mammalian alcohol dehydrogenases using nuclear magnetic resonance.
2006-06-15
Toxicity assessment of thiodiglycol.
2006-01-06
NMR analysis of thiodiglycol oxidation by Mammalian alcohol dehydrogenases.
2006
Contact angle anomalies indicate that surface-active eluates from silicone coatings inhibit the adhesive mechanisms of fouling organisms.
2006
Electrospray ionization tandem mass spectral analysis of oxidation products of precursors of sulfur mustards.
2006
Mercury transformations in chemical agent simulant as characterized by X-ray absorption fine spectroscopy.
2005-10-15
Quantitative analysis of the sulfur mustard hydrolysis product thiodiglycol (2,2'-sulfobisethanol) in in vivo microdialysates using gas chromatography coupled with pulsed flame photometric detection.
2005-07
Kinetics of degradation of sulphur mustard on impregnated carbons.
2005-05-20
Reactions of sulphur mustard on impregnated carbons.
2004-12-31
Determination of thiodiglycol, a mustard gas hydrolysis product by gas chromatography-mass spectrometry after tert-butyldimethylsilylation.
2004-12-24
Packed capillary liquid chromatography-electrospray ionization (tandem) mass spectrometry of mustard hydrolysis products in soil.
2004-11-26
Ring-opening reactions induced by gold(I) of five- and four-coordinate palladium(II) and platinum(II) complexes containing tripodal or linear polyphosphines.
2004-08-21
Oxoammonium salts. 9. Oxidative dimerization of polyfunctional primary alcohols to esters. An interesting beta oxygen effect.
2004-07-23
Quantitation of the sulfur mustard metabolites 1,1'-sulfonylbis[2-(methylthio)ethane] and thiodiglycol in urine using isotope-dilution Gas chromatography-tandem mass spectrometry.
2004-07-09
Monitoring sulfur mustard exposure by gas chromatography-mass spectrometry analysis of thiodiglycol cleaved from blood proteins.
2004-07-09
[Thiodiglycol metabolism in Alcaligenes xylosoxydans subsp. denitrificans].
2002-11-27
Percutaneous absorption of explosives and related compounds: an empirical model of bioavailability of organic nitro compounds from soil.
2002-07-15
[The bioutilization of thiodiglycol (a breakdown product of mustard gas): isolation of degraders and investigation of degradation conditions].
2002-05-25
Transformation of thiodiglycol by resting cells of Alcaligenes xylosoxydans PGH10.
2002-04-06
Analysis of the degradation compounds of chemical warfare agents using liquid chromatography/mass spectrometry.
2001-12
Overalkylation of a protein digest with iodoacetamide.
2001-08-01
Capillary gas chromatography-atomic emission spectroscopy-mass spectrometry analysis of sulphur mustard and transformation products in a block recovered from the Baltic Sea.
2001-06-01
Patents

Sample Use Guides

NOAEL (rat) 500 mg/kg/day for 90 days
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:08:41 GMT 2025
Edited
by admin
on Mon Mar 31 18:08:41 GMT 2025
Record UNII
9BW5T43J04
Record Status Validated (UNII)
Record Version
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Name Type Language
NSC-6289
Preferred Name English
THIODIGLYCOL
HSDB   INCI   INN  
INN   INCI  
Official Name English
thiodiglycol [INN]
Common Name English
THIODIGLYCOL [HSDB]
Common Name English
2,2'-THIODIETHANOL [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1590
Created by admin on Mon Mar 31 18:08:41 GMT 2025 , Edited by admin on Mon Mar 31 18:08:41 GMT 2025
Code System Code Type Description
NCI_THESAURUS
C75295
Created by admin on Mon Mar 31 18:08:41 GMT 2025 , Edited by admin on Mon Mar 31 18:08:41 GMT 2025
PRIMARY
ChEMBL
CHEMBL444480
Created by admin on Mon Mar 31 18:08:41 GMT 2025 , Edited by admin on Mon Mar 31 18:08:41 GMT 2025
PRIMARY
MERCK INDEX
m10753
Created by admin on Mon Mar 31 18:08:41 GMT 2025 , Edited by admin on Mon Mar 31 18:08:41 GMT 2025
PRIMARY Merck Index
HSDB
7482
Created by admin on Mon Mar 31 18:08:41 GMT 2025 , Edited by admin on Mon Mar 31 18:08:41 GMT 2025
PRIMARY
EPA CompTox
DTXSID6026878
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PRIMARY
INN
199
Created by admin on Mon Mar 31 18:08:41 GMT 2025 , Edited by admin on Mon Mar 31 18:08:41 GMT 2025
PRIMARY
EVMPD
SUB10977MIG
Created by admin on Mon Mar 31 18:08:41 GMT 2025 , Edited by admin on Mon Mar 31 18:08:41 GMT 2025
PRIMARY
MESH
C047519
Created by admin on Mon Mar 31 18:08:41 GMT 2025 , Edited by admin on Mon Mar 31 18:08:41 GMT 2025
PRIMARY
NSC
6289
Created by admin on Mon Mar 31 18:08:41 GMT 2025 , Edited by admin on Mon Mar 31 18:08:41 GMT 2025
PRIMARY
FDA UNII
9BW5T43J04
Created by admin on Mon Mar 31 18:08:41 GMT 2025 , Edited by admin on Mon Mar 31 18:08:41 GMT 2025
PRIMARY
CAS
111-48-8
Created by admin on Mon Mar 31 18:08:41 GMT 2025 , Edited by admin on Mon Mar 31 18:08:41 GMT 2025
PRIMARY
CHEBI
75184
Created by admin on Mon Mar 31 18:08:41 GMT 2025 , Edited by admin on Mon Mar 31 18:08:41 GMT 2025
PRIMARY
WIKIPEDIA
THIODIGLYCOL
Created by admin on Mon Mar 31 18:08:41 GMT 2025 , Edited by admin on Mon Mar 31 18:08:41 GMT 2025
PRIMARY
SMS_ID
100000082420
Created by admin on Mon Mar 31 18:08:41 GMT 2025 , Edited by admin on Mon Mar 31 18:08:41 GMT 2025
PRIMARY
ECHA (EC/EINECS)
203-874-3
Created by admin on Mon Mar 31 18:08:41 GMT 2025 , Edited by admin on Mon Mar 31 18:08:41 GMT 2025
PRIMARY
PUBCHEM
5447
Created by admin on Mon Mar 31 18:08:41 GMT 2025 , Edited by admin on Mon Mar 31 18:08:41 GMT 2025
PRIMARY
Related Record Type Details
ACTIVE MOIETY