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thiodiglycol
ethanol, 2,2'-thiobis-

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Name:2-(2-hydroxyethylsulfanyl)ethanol
CAS Number: 111-48-8Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:203-874-3
FDA UNII: 9BW5T43J04
Nikkaji Web:J1.988G
Beilstein Number:1236325
MDL:MFCD00002910
XlogP3:-0.60 (est)
Molecular Weight:122.18710000
Formula:C4 H10 O2 S
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:antioxidants
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
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Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Appearance:colorless liquid (est)
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Specific Gravity:1.22100 @ 25.00 °C.
Melting Point: -10.20 °C. @ 760.00 mm Hg (est)
Boiling Point: 282.00 °C. @ 760.00 mm Hg
Vapor Pressure:0.003230 mmHg @ 25.00 °C.
Vapor Density:4.21 ( Air = 1 )
Flash Point:> 230.00 °F. TCC ( > 110.00 °C. )
logP (o/w): -0.630
Soluble in:
 water, 1.00E+06 mg/L @ 20 °C (exp)
 water, 1e+006 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
CosIng:cosmetic data
Cosmetic Uses: antioxidants
 
Suppliers:
BOC Sciences
For experimental / research use only.
Thiodiglycol 98%
Odor: characteristic
Use: Thiodiglycol, the hydrolysis product of sulfur mustard, is useful in textile dyeing and sorts of pen ink manufacturing. It could produce mustard gas reacted with hydrochloric acid and is widely used as a solvent. Thiodiglycol is useful in textile dyeing and sorts of pen ink manufacturing.
Sigma-Aldrich: Aldrich
For experimental / research use only.
2,2'-Thiodiethanol ≥99%
sds
TCI AMERICA
For experimental / research use only.
2,2'-Thiodiethanol >96.0%(GC)
sds
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-guinea pig LD50 3960 mg/kg
KIDNEY, URETER, AND BLADDER: OTHER CHANGES BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) GASTROINTESTINAL: OTHER CHANGES
Journal of Industrial Hygiene and Toxicology. Vol. 23, Pg. 259, 1941.

intravenous-rabbit LD50 3000 mg/kg
Journal of Pharmacology and Experimental Therapeutics. Vol. 93, Pg. 1, 1948.

oral-rat LD50 6610 mg/kg
Journal of Industrial Hygiene and Toxicology. Vol. 23, Pg. 259, 1941.

Dermal Toxicity:
subcutaneous-mouse LD50 4000 mg/kg
LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), DIFFUSE" GASTROINTESTINAL: OTHER CHANGES ENDOCRINE: OTHER CHANGES
Journal of Pharmacology and Experimental Therapeutics. Vol. 93, Pg. 1, 1948.

skin-rabbit LD50 20 mL/kg
Union Carbide Data Sheet. Vol. 11/3/1971

subcutaneous-rat LD50 4000 mg/kg
Journal of Pharmacology and Experimental Therapeutics. Vol. 93, Pg. 1, 1948.

Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
antioxidants
Recommendation for thiodiglycol usage levels up to:
 not for fragrance use.
 
Recommendation for thiodiglycol flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
NIOSH International Chemical Safety Cards:search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):111-48-8
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :5447
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:1
2-(2-hydroxyethylsulfanyl)ethanol
Chemidplus:0000111488
RTECS:111-48-8
 
References:
 2-(2-hydroxyethylsulfanyl)ethanol
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:111-48-8
Pubchem (cid):5447
Pubchem (sid):134975177
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
HMDB (The Human Metabolome Database):Search
Export Tariff Code:2930.90.5050
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
 antioxidants
 
Occurrence (nature, food, other):note
 not found in nature
 
Synonyms:
 dihydroxyethyl sulfide
 ethanol, 2,2'-thiobis-
 ethanol, 2,2'-thiodi-
 glyecine A
bis(2-hydroxyethyl) sulfide
bis(b-hydroxyethyl) sulfide
bis(2-hydroxyethyl) sulphide
2-[(2-hydroxyethyl)sulfanyl]ethan-1-ol
bis(hydroxyethyl)sulfide
bis(2-hydroxyethyl)sulfide
2-[(2-hydroxyethyl)thio]ethanol
2-(2-hydroxyethylsulfanyl)ethanol
2-(2-hydroxyethylthio)ethan-1-ol
2-(2-hydroxyethylthio)ethanol
 kromfax solvent
2,2'-sulfanediyldiethanol
 tedegyl
2,2'-thiobis(ethanol)
2,2'-thiobis[ethanol]
2,2'-thiobisethanol
2,2-thiodiethanol
2,2'-thiodiethanol
 thiodiethylene glycol
2,2'-thiodiglycol
 tiodiglicolo
 

Articles:

PubMed:Demonstration of spread-on peel-off consumer products for sampling surfaces contaminated with pesticides and chemical warfare agent signatures.
PubMed:Determination of mustard gas hydrolysis products thiodiglycol and thiodiglycol sulfoxide by gas chromatography tandem-mass spectrometry after trifluoroacetylation.
PubMed:Abundance of four sulfur mustard-DNA adducts ex vivo and in vivo revealed by simultaneous quantification in stable isotope dilution-ultrahigh performance liquid chromatography-tandem mass spectrometry.
PubMed:On-matrix derivatization extraction of chemical weapons convention relevant alcohols from soil.
PubMed:Historical perspective on effects and treatment of sulfur mustard injuries.
PubMed:[Strain Alcaligenes xylosoxydans subsp. Denitrificans TD2 as a biosensor basis for determination of thiodiglycol].
PubMed:Detection and identification of hydrolysis products of sulfur mustards at trace levels in environmental samples using liquid chromatography solid phase extraction combined with off-line nuclear magnetic resonance analysis.
PubMed:Simultaneous quantification of seven plasma metabolites of sulfur mustard by ultra high performance liquid chromatography-tandem mass spectrometry.
PubMed:On-matrix derivatization for dynamic headspace sampling of nonvolatile surface residues.
PubMed:Soil biotransformation of thiodiglycol, the hydrolysis product of mustard gas: understanding the factors governing remediation of mustard gas contaminated soil.
PubMed:[Destruction of mustard gas hydrolysis products by marine and soil bacteria].
PubMed:Subgross breast pathology in the twenty-first century.
PubMed:The reactivity of quaternary ammonium- versus potassium-fluorides supported on metal oxides: paving the way to an instantaneous detoxification of chemical warfare agents.
PubMed:Analysis of hazardous organic residues from sodium hydrosulfite industry and utilization as raw materials in a novel solid lubricant production.
PubMed:Dispersive derivatization liquid-liquid extraction of degradation products/precursors of mustards and V-agents from aqueous samples.
PubMed:New reagents for enhanced liquid chromatographic separation and charging of intact protein ions for electrospray ionization mass spectrometry.
PubMed:Locus-specific microemulsion catalysts for sulfur mustard (HD) chemical warfare agent decontamination.
PubMed:Microbial responses to mustard gas dumped in the Baltic Sea.
PubMed:Modified titania nanotubes for decontamination of sulphur mustard.
PubMed:Screening hydrolysis products of sulfur mustard agents by high-performance liquid chromatography with inductively coupled plasma mass spectrometry detection.
PubMed:New insights into the biodegradation of thiodiglycol, the hydrolysis product of Yperite (sulfur mustard gas).
PubMed:Biodegradation of thiodiglycol, a hydrolyzate of the chemical weapon Yperite, by benzothiophene-desulfurizing bacteria.
PubMed:Reactions of sulphur mustard and sarin on V 1.02 O 2.98 nanotubes.
PubMed:Mercury transformations in chemical agent simulant as characterized by X-ray absorption fine spectroscopy.
PubMed:Kinetics of the degradation of sulfur mustard on ambient and moist concrete.
PubMed:Improvements in the methodology of monitoring sulfur mustard exposure by gas chromatography-mass spectrometry analysis of cleaved and derivatized blood protein adducts.
PubMed:Analysis of urinary metabolites of sulfur mustard in two individuals after accidental exposure.
PubMed:Developmental toxicity of thiodiglycol in Sprague-Dawley rats.
PubMed:The effect of mustard gas on the biological activity of soil.
PubMed:Soil bacterium Pseudomonas sp.: destroyer of mustard gas hydrolysis products.
PubMed:Application of in vivo microdialysis for studying the efficacy of protective preparations against sulfur mustard penetrating the skin.
PubMed:Destruction of chemical agent simulants in a supercritical water oxidation bench-scale reactor.
PubMed:Contact angle anomalies indicate that surface-active eluates from silicone coatings inhibit the adhesive mechanisms of fouling organisms.
PubMed:Analysis of the sulphur mustard metabolites thiodiglycol and thiodiglycol sulphoxide in urine using isotope-dilution gas chromatography-ion trap tandem mass spectrometry.
PubMed:NMR analysis of thiodiglycol oxidation by Mammalian alcohol dehydrogenases.
PubMed:Electrospray ionization tandem mass spectral analysis of oxidation products of precursors of sulfur mustards.
PubMed:Thiodiglycol, the hydrolysis product of sulfur mustard: analysis of in vitro biotransformation by mammalian alcohol dehydrogenases using nuclear magnetic resonance.
PubMed:Toxicity assessment of thiodiglycol.
PubMed: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.
PubMed:Kinetics of degradation of sulphur mustard on impregnated carbons.
PubMed:Determination of thiodiglycol, a mustard gas hydrolysis product by gas chromatography-mass spectrometry after tert-butyldimethylsilylation.
PubMed:Reactions of sulphur mustard on impregnated carbons.
PubMed:Packed capillary liquid chromatography-electrospray ionization (tandem) mass spectrometry of mustard hydrolysis products in soil.
PubMed:Ring-opening reactions induced by gold(I) of five- and four-coordinate palladium(II) and platinum(II) complexes containing tripodal or linear polyphosphines.
PubMed:Quantitation of the sulfur mustard metabolites 1,1'-sulfonylbis[2-(methylthio)ethane] and thiodiglycol in urine using isotope-dilution Gas chromatography-tandem mass spectrometry.
PubMed:Monitoring sulfur mustard exposure by gas chromatography-mass spectrometry analysis of thiodiglycol cleaved from blood proteins.
PubMed:[Thiodiglycol metabolism in Alcaligenes xylosoxydans subsp. denitrificans].
PubMed:[The bioutilization of thiodiglycol (a breakdown product of mustard gas): isolation of degraders and investigation of degradation conditions].
PubMed:Transformation of thiodiglycol by resting cells of Alcaligenes xylosoxydans PGH10.
PubMed:Analysis of the degradation compounds of chemical warfare agents using liquid chromatography/mass spectrometry.
PubMed:Capillary gas chromatography-atomic emission spectroscopy-mass spectrometry analysis of sulphur mustard and transformation products in a block recovered from the Baltic Sea.
PubMed:Reactions of VX, GB, GD, and HD with nanosize Al(2)O(3). Formation of aluminophosphonates.
PubMed:Diagnosis and dosimetry of exposure to sulfur mustard: development of a standard operating procedure for mass spectrometric analysis of haemoglobin adducts: exploratory research on albumin and keratin adducts.
PubMed:A cutaneous full-thickness liquid sulfur mustard burn model in weanling swine: clinical pathology and urinary excretion of thiodiglycol.
PubMed:Determination of thiodyglycol in groundwater using solid-phase extraction followed by gas chromatography with mass spectrometric detection in the selected-ion mode.
PubMed:Extraction of thiodiglycol from soil using pressurised liquid extraction.
PubMed:Oxidation of thiodiglycol (2,2'-thiobis-ethanol) by alcohol dehydrogenase: comparison of human isoenzymes.
PubMed:Biocatalytic transformation of [(2-Hydroxyethyl)thio]acetic acid and thiodiglycolic acid from thiodiglycol by Alcaligenes xylosoxydans ssp. xylosoxydans (SH91).
PubMed:Determination of hydrolysis products of sulfur mustards by reversed-phase microcolumn liquid chromatography coupled on-line with sulfur flame photometric detection and electrospray ionization mass spectrometry using large-volume injections and peak compression
PubMed:The sources, fate, and toxicity of chemical warfare agent degradation products.
PubMed:Determination of the sulfur mustard hydrolysis product thiodiglycol by microcolumn liquid chromatography coupled on-line with sulfur flame photometric detection using large-volume injections and peak compression.
PubMed:Estimation of the Surface Properties of Styrene-Acrylonitrile Random Copolymers from Contact Angle Measurements.
PubMed:Characterization of the Batl (Bacteroides aerotolerance) operon in Bacteroides fragilis: isolation of a B. fragilis mutant with reduced aerotolerance and impaired growth in in vivo model systems.
PubMed:In vitro oxidation of the hydrolysis product of sulfur mustard, 2,2'-thiobis-ethanol, by mammalian alcohol dehydrogenase.
PubMed:Recovery of an oligonucleotide using silver ions immobilized onto paramagnetic particles.
PubMed:Fungal cleavage of thioether bond found in Yperite.
PubMed:Observations of metabolite formation and variable yield in thiodiglycol biodegradation process : impact on reactor design.
PubMed:Effect of sulphur mustard on the expression of urokinase in cultured 3T3 fibroblasts.
PubMed:Bioreactor strategies for the treatment of growth-inhibitory waste: an analysis of thiodiglycol degradation, the main hydrolysis product of sulfur mustard.
PubMed:The role of a liquid matrix in controlling FAB-induced fragmentation.
PubMed:Reactor comparisons for the biodegradation of thiodiglycol, a product of mustard gas hydrolysis.
PubMed:[Scientific principles of complex ecologically-safe technology of mustard gas destruction].
PubMed:Detection of sulfur mustard bis (2-chloroethyl) sulfide and metabolites after topical application in the isolated perfused porcine skin flap.
PubMed:Improved methodology for the detection and quantitation of urinary metabolites of sulphur mustard using gas chromatography-tandem mass spectrometry.
PubMed:Biological fate of sulphur mustard, 1,1'-thiobis(2-chloroethane): identification of beta-lyase metabolites and hydrolysis products in human urine.
PubMed:Application of gas chromatography-mass spectrometry and gas chromatography-tandem mass spectrometry to the analysis of chemical warfare samples, found to contain residues of the nerve agent sarin, sulphur mustard and their degradation products.
PubMed:Metabolism of thiodiglycol (2,2'-thiobis-ethanol): isolation and identification of urinary metabolites following intraperitoneal administration to rat.
PubMed:Biological fate of sulphur mustard, 1,1'-thiobis(2-chloroethane): isolation and identification of urinary metabolites following intraperitoneal administration to rat.
PubMed:Biological fate of sulfur mustard, 1,1'-thiobis(2-chloroethane). Urinary excretion profiles of hydrolysis products and beta-lyase metabolites of sulfur mustard after cutaneous application in rats.
PubMed:Development of an antibody that binds sulfur mustard.
PubMed:N1-(2-hydroxyethylthioethyl)-4-methyl imidazole (4-met-1-imid-thiodiglycol) in plasma and urine: a novel metabolite following dermal exposure to sulphur mustard.
PubMed:Methods for the analysis of thiodiglycol sulphoxide, a metabolite of sulphur mustard, in urine using gas chromatography-mass spectrometry.
PubMed:Biosynthesis and urinary excretion of methyl sulfonium derivatives of the sulfur mustard analog, 2-chloroethyl ethyl sulfide, and other thioethers.
PubMed:Quantification of thiodiglycol in urine by electron ionization gas chromatography-mass spectrometry.
PubMed:[Evaluation of the critical surface tension (gc) of composite resins].
PubMed:Detection of trace levels of thiodiglycol in blood, plasma and urine using gas chromatography-electron-capture negative-ion chemical ionisation mass spectrometry.
PubMed:Analysis of thiodiglycol in urine of victims of an alleged attack with mustard gas, Part II.
PubMed:Determination of ascorbic acid in human urine by high-performance liquid chromatography coupled with fluorimetry after post-column derivatization with benzamidine.
PubMed:Analysis of thiodiglycol in urine of victims of an alleged attack with mustard gas.
PubMed:Separation of ascorbic acid, dehydroascorbic acid, diketogulonic acid and glucose by isocratic elution from a column of a hydrophilic gel.
PubMed:The analysis of acyl-coenzyme A derivatives by reverse-phase high-performance liquid chromatography.
PubMed:Cerebrospinal fluid protein electrophoresis without prior concentration.
PubMed:Cerebrospinal fluid proteins electrophoresis without prior concentration.
PubMed:The effect of thiodiglycol and dithiothreitol on the alkaline hydrolysis products of certain amino acid phenylthiohydantoins.
PubMed:The respiratory metabolism of Mycobacterium lepraemurium.
PubMed:Stabilization of the final product in the Sakaguchi reaction by thiodiglycol.
PubMed:Utilization of sulfur compounds by Streptococcus bovis.
PubMed:[Use of a derivative from the hydrolysis of yperite: thiodiglycol in cancerology].
PubMed:The rate of oxidation of thiodiglycol and triethylamine by hydrogen peroxide.
 
Notes:
product of yperite hydrolysis; a hydrolysis product opf mustard gas; strongly stimulates differentiation of chick embryo myogenic cells.
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