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DL-Dithiothreitol (DTT)

CAS 3483-12-3 ≥95%

DL-Dithiothreitol (DTT) | CAS 3483-12-3 | ≥95%

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Technical Specifications

CAS Number 3483-12-3
EC / EINECS Number 222-468-7
MDL Number MFCD00004877
RTECS Number EK1610000
SMILES C([C@@H]([C@H](CS)O)O)S
InChI InChI=1S/C4H10O2S2/c5-3(1-7)4(6)2-8/h3-8H,1-2H2/t3-,4-/m0/s1
InChIKey VHJLVAABSRFDPM-IMJSIDKUSA-N
PubChem CID 439196
Molecular Formula C₄H₁₀O₂S₂
Molecular Weight 154.25 g/mol
Melting Point 41–44 °C
Solubility Highly soluble in water (50 mg/mL), ethanol, chloroform, diethyl ether, ethyl acetate
Log Pow 0.07 at pH 5.0 and 25 °C
Purity ≥95%
Physical Form White crystalline powder
HS Code 2930.90
Shelf Life Retest period: 12 months from date of manufacture
Storage Conditions Store refrigerated (2–8 °C) in a tightly sealed container under inert atmosphere, protected from moisture

Product Description & Scientific Applications

DL-Dithiothreitol (DTT; Cleland's reagent) is a water-soluble dithiol that reduces disulfide bonds to the corresponding thiols. Reduction proceeds by two sequential thiol–disulfide exchanges. The first opens the substrate disulfide to a mixed disulfide. The second closes intramolecularly to give oxidised DTT, the six-membered cyclic disulfide trans-4,5-dihydroxy-1,2-dithiane. Producing two products from one reactant displaces the equilibrium toward reduction, particularly in dilute solution. DTT has a redox potential of −0.33 V at pH 7.

pH and thiolate dependence. Only the deprotonated thiolate is nucleophilic. DTT therefore reduces fastest above pH 7, and is sluggish near neutrality, where most of its thiol groups are protonated. Disulfide reduction finishes within a few minutes at pH 8 but is far slower at pH 7.

Advantage over monothiols. The ring-closing step is faster than the initial intermolecular exchange, so the mixed-disulfide intermediate does not accumulate. Monothiol reductants such as glutathione, cysteine and 2-mercaptoethanol have exchange equilibria near unity and must be used in large excess.

Disulfide reduction. In the laboratory DTT is the standard reagent for this reduction, used on disulfides in both small molecules and proteins. Reduction of cystine runs to completion even when oxidised DTT is present in tenfold excess.

Protecting thiols. DTT also keeps thiol groups in the reduced state. It protects the sulfhydryl groups of coenzyme A and of enzymes against air oxidation to disulfides.

Solubility, odour and stability. DTT is a highly water-soluble solid of little odour. Its reduced solutions resist air oxidation better than glutathione, though oxidation is catalysed by monothiols such as cysteine. Oxidised DTT absorbs near 283 nm, allowing the extent of oxidation to be checked spectrophotometrically.

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Safety Information

GHS Pictograms
GHS07 Harmful/Irritant
Signal Word Warning
Hazard Class None — not subject to transport regulations
Transport Category Not classified as dangerous goods for transport (ADR/IATA/IMDG)
H-Statements H302 - H315 - H319
P-Statements P264 - P270 - P280 - P301+P312 - P302+P352 - P305+P351+P338 - P332+P313 - P337+P313 - P501

Documentation

Safety Data Sheet Download PDF
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