27565-41-9

Basic information

• Product Name: DL-Dithiothreitol
• Synonyms: DTT-MBG;DTT (RACEMIC);DL-THREO-2,3-DIHYDROXY-1,4-DITHIOLBUTANE;DL-THREO-1,4-DIMERCAPTO-2,3-BUTANEDIOL;DL-DITHIOTHREITOL;DL-DTT;DITHIOTHREITOL, 1,4-;DITT
• CAS NO: 27565-41-9
• Molecular Formula: C₄H₁₀O₂S₂
• Molecular Weight: 154.25
• EINECS: 222-468-7
• Product Categories: Biochemistry;O-Substituted Sugars;Sugar Alcohols;Sugars;Reagents for Electrophoresis
• Mol File: 27565-41-9.mol
• Article Data: 19

Chemical Properties

• Melting Point: 41-44 °C(lit.)
• Boiling Point: 125-130 °C (2 mmHg)
• Flash Point: >230 °F
• Appearance: White/Liquid
• Density: 1.04 g/mL at 20 °C
• Refractive Index: 1.5200 (estimate)
• Storage Temp.: 2-8°C
• Solubility: H2O: 50 mg/mL, clear, colorless
• Water Solubility: Soluble
• Merck: 3376
• CAS DataBase Reference: DL-Dithiothreitol(CAS DataBase Reference)
• NIST Chemistry Reference: DL-Dithiothreitol(27565-41-9)
• EPA Substance Registry System: DL-Dithiothreitol(27565-41-9)

Safety Data

• Hazard Codes: Xn
• Statements: 25-36/37/38-22
• Safety Statements: 26-45-36
• WGK Germany: 3
• RTECS: EK1610000
• F: 3-10-16-23
• Hazardous Substances Data: 27565-41-9(Hazardous Substances Data)

Usage

Chemical Properties

White solid

Uses

Different sources of media describe the Uses of 27565-41-9 differently. You can refer to the following data:
1. Reagent for the quantitative reduction of disulfide group. Prevents the oxidation of cholecystokinin during its extraction from brain and duodenal tissues. Cleavage of disulfide bonds in proteins.
2. DTT is a cell permeable protective agent for Thiol groups.

Preparation

The preparation of DL-Dithiothreitol is as follows:To a round bottom flask was charged THPP (23mg, 0.11mmol, 1.10eq) and the basic buffer solution [tris-(hydroxymethyl)-aminomethane-CaCl2 based buffer; pH 8.00; 1.0mL]. The reaction mixture was stirred at room temperature for about 5 min and then to this homogenous solution was charged trans-4,5-Dihydroxy-1,2-dithiane (15.2mg, 0.10 mmol, 1.00eq.). The reaction mixture was stirred at room temperature until the reaction was complete (about 30 min). The product was readily identified by 1H-NMR analysis.

Purification Methods

Crystallise DTT from ether and sublime it at 37o/0.005mm. It should be stored at 0o. [Beilstein 1 III 2360.]

InChI:InChI=1/C4H10O2S2/c1-2(5)3(6)4(7)8/h2-8H,1H3

Upstream product

• 462-20-4 dihydrolipoic acid 
• 16096-98-3 trans-1,2-dithiane-4,5-diol 
• 930-22-3 epoxybutene 
• 564-00-1 1,2:3,4-Diepoxybutane 
• 40227-25-6 cis-4,5-dihydroxy-1,2-dithiane 
• 60-24-2 2-hydroxyethanethiol 
• 145626-88-6 N,N'-Dicarbomethoxy-N,N'-bis(mercaptomethyl)ethylenediamine 
• 145626-91-1 N,N'-Dicarbethoxy-N,N'-bis(mercaptomethyl)hydrazine 
• 145626-89-7 N,N'-Bis(2-mercaptoacetyl)hexahydropyridazine 
• 145626-92-2 1,2-Bis(mercaptomethyl)-4-methylurazole 
• 145626-90-0 N,N'-Bis(2-mercaptoacetyl)-N-tert-butylhydrazine 
• 145626-87-5 Bis(2-mercaptoethyl) Sulfone 
• 38705-47-4 2-Mercaptoethyl Thioglycolate 
• 93464-95-0 d(-Cys-Gly) 

Downstream Products

• 74185-01-6 4,5-dihydroxy-1,2-dithiane 
• 108-98-5 thiophenol 
• 116504-33-7 <2>(2,6)Naphthalino<2>paracyclophan-1,11-dien 
• 882-33-7 diphenyldisulfane 
• 462-20-4 dihydrolipoic acid 
• 16096-98-3 trans-1,2-dithiane-4,5-diol 
• 106991-84-8 2-(2-oxo-1,2-diphenyl-ethylsulfanyl)-1,2-diphenyl-ethanone 
• 70-18-8 glutathion 
• 109759-02-6 1-(2-Chloro-phenyl)-1-(2,3-dihydroxy-4-mercapto-butylsulfanyl)-nonan-3-one 
• 109770-04-9 1,4-Bis<1-(2-Chlorophenyl)-3-oxo-nonylthio>-2,3-dihydroxybutane 
• 135598-55-9 (2-{(2S,3S)-2,3-Dihydroxy-4-[2-(4-methoxy-benzyloxycarbonylamino)-ethyldisulfanyl]-butyldisulfanyl}-ethyl)-carbamic acid 4-methoxy-benzyl ester 
• 14193-38-5 C₄H₈O₂S₂^(1-) 
• 108-95-2 phenol 
• 60-24-2 2-hydroxyethanethiol 

Relevant articles and documents

Syntheses and Structural Characterization of Water-Soluble Selenium Reagents for the Redox Control of Protein Disulfide Bonds

A new class of water-soluble redox reagents (1-4) that contain selenium as the active site was developed for the purpose of the redox control of protein structures. The X-ray crystallographic analyses revealed that trans-3,4-dihydroxy-1-selenolane (DHSred) (1) and its Se-oxide (DHSox) (2) have two axial hydroxy groups on the selenolane five-membered ring, whereas trans-1,2-diselenane-4,5-diol (DSTox) (3), a selenium analog of oxidized dithiotreiotol (DDTox), has two equatorial hydroxy groups on the diselenane six-membered ring. According to the vicinal 3JHH coupling constants observed for 1-3, it was suggested that they adopt similar structures in solution to those in the solid state. Diselenothreitol (DSTred (4), a selenium analog of dithiothreitol (DTTred), was also synthesized, but it was too air sensitive to be isolated. The reactions of 1-4 with DTTox and DTTred indicated that the oxidizing power of DHSox (2) exceeds by far that of DTTox, while the reducing power of DSTred (4) exceeds that of DTTred.

Charge Accumulation and Multi-Electron Photoredox Chemistry with a Sensitizer–Catalyst–Sensitizer Triad

Photoinduced electron transfer in donor–sensitizer–acceptor compounds usually leads to simple electron–hole pairs, and photoredox catalysis typically relies on single-electron transfer (SET) events. This work reports on a molecular triad able to accumulate two electrons on a central dibenzo[1,2]dithiin moiety flanked by two peripheral RuII photosensitizers. Under continuous illumination, the doubly reduced form of the dibenzo[1,2]dithiin undergoes thiolate–disulfide exchange with an aliphatic disulfide substrate, thereby acting as a two-electron catalyst after two initial SET events with triethylamine at the RuII sensitizers. The use of a relatively simple triad for coupling two separate SET processes to a subsequent two-electron reduction is an important conceptual advance from photoinduced SET and light-driven charge accumulation towards multi-electron photoredox catalysis. This is relevant for artificial photosynthesis and light-driven multi-electron chemistry in general.

Thiols and selenols as electron-relay catalysts for disulfide-bond reduction

Pass them on! Dithiobutylamine immobilized on a resin is a useful reagent for the reduction of disulfide bonds. Its ability to reduce a disulfide bond in a protein is enhanced greatly if used along with a soluble strained cyclic disulfide or mixed diselenide that relays electrons from the resin to the protein. This electron-relay catalysis system provides distinct advantages over the use of excess soluble reducing agent alone. Copyright