Dithioerythritol (HCID 439352)

Overview

Dithioerythritol is the meso-diastereomer of 1,4-dimercaptobutane-2,3-diol; a sulfur-containing sugar derived from the monosaccharide erythrose; and an epimer of dithiothreitol. It has a role as a reducing agent.

Names & identifiers

Preferred name: Dithioerythritol
IUPAC: (2R,3S)-1,4-bis(sulfanyl)butane-2,3-diol
English name: Dithioerythritol
Molecular formula: C4H10O2S2
Molecular weight: 154.25

Names & synonyms

Dithioerythritol6892-68-81,4-DithioerythritolDithioerythreitol(2R,3S)-1,4-DIMERCAPTOBUTANE-2,3-DIOL2,3-Butanediol, 1,4-dimercapto-, (2R,3S)-rel-(2R,3S)-1,4-disulfanylbutane-2,3-diolerythro-1,4-Dimercapto-2,3-butanediolR4SVL81GQIDTXSID40884341(2R*,3S*)-1,4-dimercapto-2,3-butanediol2,3-Butanediol, 1,4-dimercapto-, (R*,S*)-

Show more names

Cleland's reagentCLELAND REAGENT1,4-DIMERCAPTO-2,3-BUTANEDIOLRHODOVIOL 25/140DL-DITHIOERYTHRITOLDTE, Reducing agent

CHEBI:17456RefChem:135200GlyTouCan:G15985JFDTXCID801023788G15985JF229-998-8DTE(2R,3S)-1,4-bis(sulfanyl)butane-2,3-diol

Database identifiers

CAS: 6892-68-8
PubChem CID: 439352
DTXSID: DTXSID40884341
ChEMBL: CHEMBL1232391
ChEBI: CHEBI:17456
UNII: R4SVL81GQI
EC Number: 229-998-8
Nikkaji: J136.609B

Properties

Computed structural properties

XLogP: -0.4
Topological polar surface area: 42.5 Å²
Hydrogen bond donors: 4
Hydrogen bond acceptors: 4
Rotatable bonds: 3
Heavy atoms: 8
Formal charge: 0
Complexity: 52

Experimental & physicochemical properties

Chemical ClassesBiological Agents -> Monosaccharides and Derivatives

DrugsPharmaceuticals -> Listed in ZINC15

Physical DescriptionWhite powder; [Sigma-Aldrich MSDS]

Physicochemical properties

Melting point: 82 · 82-84 °C(lit.)
Boiling point: 247.65 °C · 247.65°C (rough estimate)
Density: 1.156 · 1.156 (estimate)
refractive index: 1.52 · 1.5200 (estimate)
storage temp.: 2 · 2-8°C
solubility: 2 O: · H2O: 10 mg/mL, clear, colorless
form: Powder
pka: 1 · pK1:9.5 (25°C)
color: White to pale yellow or beige
PH: 4 · 4.0-6.0 (25℃, 0.1M in H2O)
Water Solubility: Soluble
Sensitive: Air Sensitive
λmax: 260 nm · λ: 260 nm Amax: 0.400λ: 280 nm Amax: 0.050
BRN: 1719756 · 1719756
Stability: Stable. Combustible. Incompatible with strong oxidizing agents.
InChI: 1S/C4H10O2S2/c5-3(1-7)4(6)2-8/h3-8H,1-2H2/t3-,4+
InChIKey: VHJLVAABSRFDPM-ZXZARUISSA-N
SMILES: SC[C@H](O)[C@H](O)CS
CAS DataBase Reference: 6892 · 6892-68-8(CAS DataBase Reference)
FDA UNII: 4 SVL81GQI · R4SVL81GQI
EPA Substance Registry System: 1 · 1,4-Dithioerythritol (6892-68-8)
Absorption: 0.4 at · ≤0.4 at 280 in H2O at 0.1M≤0.6 at 260 in H2O at 0.1M
UNSPSC Code: 12352201 · 12352201
NACRES: 31 · NA.31
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302-H412
Precautionary statements: 273 · P273-P301+P312+P330
Hazard Codes: Xi,Xn
Risk Statements: 36 · 36/37/38-22
Safety Statements: 26 · 26-36-37/39
RIDADR: 3335 · UN 3335
WGK Germany: 3 · 3
RTECS: 2410000 · KF2410000
F: 3 · 3-10-13-23
TSCA: TSCA listed
HazardClass: 9 · 9
HS Code: 29309070 · 29309070
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 4 OralAquatic · Acute Tox. 4 OralAquatic Chronic 3

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H315 (98.1%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 54 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 2 items

Chemical: 2,3-Butanediol, 1,4-dimercapto-, (R*,S*)-

2,3-Butanediol, 1,4-dimercapto-, (2R,3S)-rel-: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryCauses convulsions in intramuscular lethal-dose studies of mice (LD50 = 309 mg/kg); [RTECS] A skin and strong eye irritant; May cause CNS depression; [Sigma-Aldrich MSDS]

Hazard Classes and CategoriesSkin Irrit. 2 (98.1%)

Safety & protection

Protective Action Criteria (PAC) · 3 items

1.5 [mg/m3]

17 [mg/m3]

99 [mg/m3]

Safety data

F: 3-10-13-23
wgk: 3
tsca: TSCA listed
rtecs: KF2410000
ridadr: UN 3335
hs_code: 29309070
risk_code: 36/37/38-22
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi,Xn
safety_code: 26-36-37/39
hazard_class: 9
Storage Class: 11 - Combustible Solids
Hazard statements: H302-H412
Hazard Classifications: Acute Tox. 4 OralAquatic Chronic 3
Precautionary statements: P273-P301+P312+P330

Chemistry & industry

Pharmacology

MeSH Pharmacological ClassificationChemical agents that react with SH groups. This is a chemically diverse group that is used for a variety of purposes. Among these are enzyme inhibition, enzyme reactivation or protection, and labelling.

Uses & manufacturing

UsesUsed as a reagent to prevent oxidation of sulfhydryl groups and to reduce disulfides to sulfhydryl groups; [ChemIDplus]

General Manufacturing Information2,3-Butanediol, 1,4-dimercapto-, (2R,3S)-rel-: ACTIVE

Applications · 3 items

UsesReagent for the reduction of disulfide group. Prevents oxidation of sulfhydryl-containing proteins during SDS-polyacrylamide gel electrophoresis. Cleavage of disulfide bonds in proteins

Uses1,4-Dithioerythritol is a Michael reaction acceptor; inducers of enzymes that protect against carcinogenesis: reactivity with sulfhydryl groups.

UsesReagent for maintaining SH groups in the reduced state; quantitatively reduces disulfides.

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]

北京华美互利生物化工010-56205725 · [email protected]

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

湖南韵邦生物科技股份有限公司85561037 15386497078 · [email protected]

Additional notes

DefinitionChEBI: The meso-diastereomer of 1,4-dimercaptobutane-2,3-diol; a sulfur-containing sugar derived from the monosaccharide erythrose; and an epimer of dithiothreitol.