6892-68-8

Usage

Uses

Used in Biochemistry Research:
Dithioerythritol is used as a reagent for the reduction of disulfide groups in proteins, which is essential for studying protein structure and function. It prevents the oxidation of sulfhydryl-containing proteins during SDS-polyacrylamide gel electrophoresis, ensuring accurate protein separation and analysis.
Used in Enzyme Induction:
Dithioerythritol acts as a Michael reaction acceptor and can induce enzymes that protect against carcinogenesis. Its reactivity with sulfhydryl groups allows it to modulate cellular processes and potentially contribute to cancer prevention.
Used in Protein Modification:
Dithioerythritol is used as a reagent for maintaining thiol (-SH) groups in the reduced state, which is crucial for the proper folding and function of proteins. It can quantitatively reduce disulfide bonds, enabling researchers to study and manipulate protein structure and function.
Used in Pharmaceutical Development:
Due to its ability to cleave disulfide bonds in proteins, Dithioerythritol may have potential applications in the development of drugs targeting protein misfolding and aggregation, which are associated with various diseases, including neurodegenerative disorders and certain cancers.

Purification Methods

Crystallise DTE from ether/hexane and store it in the dark at 0o. [Beilstein 1 III 2360.]

InChI:InChI=1/C4H10O2S2/c5-3(1-7)4(6)2-8/h3-8H,1-2H2/t3-,4+

Synthetic route

2,3-diacetylthiomethyl ethylene oxide → 1,4-dithio-erythritol (6892-68-8)

Conditions	Yield
With sodium hydroxide In water at 50℃; for 5h; Reagent/catalyst;	83%

C4H10O8S2 → 1,4-dithio-erythritol (6892-68-8)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 25℃; for 18h;	79%

cis-4,5-dihydroxy-1,2-dithiane (40227-25-6) → 1,4-dithio-erythritol (6892-68-8)

Conditions	Yield
With tris-(2-carboxyethyl)-phosphine hydrochloride; potassium carbonate In methanol; chloroform; water at 20℃; for 6h;	70%

Dithiothreitoltetraacetat (1194723-61-9) → 1,4-dithio-erythritol (6892-68-8)

Conditions	Yield
With hydrogenchloride In methanol at 25℃; for 5h; Inert atmosphere;	70%

tetraacetyl derivative of erythro-1.4-dimercapto-butanediol-(2.3) → 1,4-dithio-erythritol (6892-68-8)

Conditions	Yield
With hydrogenchloride

epoxybutene (930-22-3) + 1,2:3,4-Diepoxybutane (564-00-1, 1464-53-5, 30031-64-2, 30419-67-1, 34897-03-5, 298-18-0) → 1,4-dithio-erythritol (6892-68-8) + 1,4-dithio-D,L-threitol (27565-41-9)

Conditions	Yield
With sodium hydroxide; water In methanol; water at 20 - 35℃; under 4500.45 Torr; for 14h;

1,4-dithio-erythritol (6892-68-8) → cis-4,5-dihydroxy-1,2-dithiane (40227-25-6)

Conditions	Yield
With 2-(4-nitrophenyl)-1,2-benzoisoselenazole-3(2H)-one; dihydrogen peroxide In d(4)-methanol for 2h; Reagent/catalyst;	100%
In dimethyl sulfoxide at 110℃; for 3h;	92%
With potassium hydroxide; oxygen In methanol at 20℃; for 60h;	65%
With oxygen; potassium hydroxide In methanol; water for 48h;

1,4-dithio-erythritol (6892-68-8) + bicyclopropylidene (27567-82-4) → (2R,3S)-1,4-Bis-(bicyclopropyl-1-ylsulfanyl)-butane-2,3-diol

Conditions	Yield
In benzene-d6 at 75℃; for 2h; in dark;	99%

1,4-dithio-erythritol (6892-68-8) + 4-tert-butyl-2,6-bis[(2,2'',6,6''-tetramethyl-m-terphenyl-2'-yl)methyl]benzenesulfenic acid (186256-53-1) → (2R,3S)-1-[4-tert-Butyl-2,6-bis-(2,6,2'',6''-tetramethyl-[1,1';3',1'']terphenyl-2'-ylmethyl)-phenyldisulfanyl]-4-mercapto-butane-2,3-diol

Conditions	Yield
In dichloromethane Ambient temperature;	81%

1-bromoglycerol + ((2-p-methoxybenzyloxycarbonyl)ethyl)disulfide (167767-80-8) + 1,4-dithio-erythritol (6892-68-8) → 6,7-dihydroxy-4-thiaheptanoic acid p-methoxybenzyl ester (167767-81-9)

Conditions	Yield
With sodium bicarbonate; triethylamine; citric acid In N-methyl-acetamide; chloroform; nitrogen; water	67%

1,4-dithio-erythritol (6892-68-8) → cis-4,5-dihydroxy-1,2-dithiane (40227-25-6) + (1R,2S,7R,8S)-1,2,7,8-tetrahydroxy-4,5,10,11-tetrathiacyclododecane

Conditions	Yield
With AcOH-NaOH buffer; potassium hexacyanoferrate(III) for 24h; pH = 4.0;	A 60% B 15%

1,4-dithio-erythritol (6892-68-8) + 2-<<(2-hydroxyethyl)sulfonyl>methyl>-m-nitro-2(Z)-pentadienophenone (115321-58-9) → ((E)-(3S,4R)-3,4-Dihydroxy-1,6-dithia-cycloundec-9-en-8-yl)-(3-nitro-phenyl)-methanone (115321-74-9, 115403-95-7)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; hydroquinone In methanol at -40℃;

1,4-dithio-erythritol (6892-68-8) → C4H9O2S2 (59177-12-7, 66460-22-8, 66460-23-9)

Conditions	Yield
In water pH 3.75 (phosphate buffer), pulse radiolysis, N2O;

1,4-dithio-erythritol (6892-68-8) → C4H8O2S2(1-) (14193-38-5, 16096-98-3, 37031-12-2, 40227-25-6, 74185-01-6, 86023-22-5, 89825-28-5)

Conditions	Yield
In water pH 6.9 (phosphate buffer), pulse radiolysis, N2O;

1,4-dithio-erythritol (6892-68-8) → Octahydrodithieno<3,4-b:3',4'-e>-1,4-dithiin (81197-94-6)

Conditions	Yield
With hydrogenchloride at 75℃; Yield given;

1,4-dithio-erythritol (6892-68-8) + 3-methyl-7,8-dimethyl-10-(1'-D-ribityl)isoalloxazine (28721-76-8) → 4,5-dihydroxy-1,2-dithiane (74185-01-6) + C18H23N4O6(1-)

Conditions	Yield
With potassium chloride; acetic acid at 25℃; Rate constant; other acids;

1,4-dithio-erythritol (6892-68-8) → C4H9NO3S2

Conditions	Yield
With sodium nitrite Ambient temperature; pH 1-2;

1,4-dithio-erythritol (6892-68-8) → C4H8N2O4S2

Conditions	Yield
With sodium nitrite Ambient temperature; pH 1-2;

1,4-dithio-erythritol (6892-68-8) + C4H9NO3S2 → (2S,3R)-1-((2R,3S)-2,3-Dihydroxy-4-mercapto-butyldisulfanyl)-4-mercapto-butane-2,3-diol

Conditions	Yield
In water at 25℃; Rate constant;

1,4-dithio-erythritol (6892-68-8) + C56H58OSe (380305-91-9) → C60H66O2S2Se

Conditions	Yield
In chloroform-d1 at 20℃;	100 % Spectr.

1-bromo-butane (109-65-9) + 1,4-dithio-erythritol (6892-68-8) + shikimic acid (138-59-0) + N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine (35661-39-3) → (1R,2S,3S,4S,5R)-2-(4-Butylsulfanyl-2,3-dihydroxy-butylsulfanyl)-3,4,5-trihydroxy-cyclohexanecarboxylic acid ((S)-1-carbamoyl-ethyl)-amide

Conditions	Yield
Multistep reaction;

1-bromo-butane (109-65-9) + 1,4-dithio-erythritol (6892-68-8) + shikimic acid (138-59-0) + Fmoc-(tBu)Asp-OH (71989-14-5) → (S)-3-{[(1R,2S,3S,4S,5R)-2-(4-Butylsulfanyl-2,3-dihydroxy-butylsulfanyl)-3,4,5-trihydroxy-cyclohexanecarbonyl]-amino}-succinamic acid

Conditions	Yield
Multistep reaction;

1-bromo-butane (109-65-9) + 1,4-dithio-erythritol (6892-68-8) + shikimic acid (138-59-0) + Fmoc-Glu(OtBu)-OH (71989-18-9) → (S)-4-{[(1R,2S,3S,4S,5R)-2-(4-Butylsulfanyl-2,3-dihydroxy-butylsulfanyl)-3,4,5-trihydroxy-cyclohexanecarbonyl]-amino}-4-carbamoyl-butyric acid

Conditions	Yield
Multistep reaction;

o-fluorobenzyl bromide (446-48-0) + 1,4-dithio-erythritol (6892-68-8) + shikimic acid (138-59-0) + N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine (35661-39-3) → (1R,2S,3S,4S,5R)-2-[4-(2-Fluoro-benzylsulfanyl)-2,3-dihydroxy-butylsulfanyl]-3,4,5-trihydroxy-cyclohexanecarboxylic acid ((S)-1-carbamoyl-ethyl)-amide

Conditions	Yield
Multistep reaction;

o-fluorobenzyl bromide (446-48-0) + 1,4-dithio-erythritol (6892-68-8) + shikimic acid (138-59-0) + Fmoc-(tBu)Asp-OH (71989-14-5) → (S)-3-({(1R,2S,3S,4S,5R)-2-[4-(2-Fluoro-benzylsulfanyl)-2,3-dihydroxy-butylsulfanyl]-3,4,5-trihydroxy-cyclohexanecarbonyl}-amino)-succinamic acid

Conditions	Yield
Multistep reaction;

o-fluorobenzyl bromide (446-48-0) + 1,4-dithio-erythritol (6892-68-8) + shikimic acid (138-59-0) + Fmoc-Glu(OtBu)-OH (71989-18-9) → (S)-4-Carbamoyl-4-({(1R,2S,3S,4S,5R)-2-[4-(2-fluoro-benzylsulfanyl)-2,3-dihydroxy-butylsulfanyl]-3,4,5-trihydroxy-cyclohexanecarbonyl}-amino)-butyric acid

Conditions	Yield
Multistep reaction;

1,4-dithio-erythritol (6892-68-8) + 1-bromo-octane (111-83-1) + shikimic acid (138-59-0) + N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine (35661-39-3) → (1R,2S,3S,4S,5R)-2-(2,3-Dihydroxy-4-octylsulfanyl-butylsulfanyl)-3,4,5-trihydroxy-cyclohexanecarboxylic acid ((S)-1-carbamoyl-ethyl)-amide

Conditions	Yield
Multistep reaction;

1,4-dithio-erythritol (6892-68-8) + 1-bromo-octane (111-83-1) + shikimic acid (138-59-0) + Fmoc-(tBu)Asp-OH (71989-14-5) → (S)-3-{[(1R,2S,3S,4S,5R)-2-(2,3-Dihydroxy-4-octylsulfanyl-butylsulfanyl)-3,4,5-trihydroxy-cyclohexanecarbonyl]-amino}-succinamic acid

Conditions	Yield
Multistep reaction;

1,4-dithio-erythritol (6892-68-8) + 1-bromo-octane (111-83-1) + shikimic acid (138-59-0) + Fmoc-Glu(OtBu)-OH (71989-18-9) → (S)-4-Carbamoyl-4-{[(1R,2S,3S,4S,5R)-2-(2,3-dihydroxy-4-octylsulfanyl-butylsulfanyl)-3,4,5-trihydroxy-cyclohexanecarbonyl]-amino}-butyric acid

Conditions	Yield
Multistep reaction;

1,4-dithio-erythritol (6892-68-8) + bromoacetic acid tert-butyl ester (5292-43-3) + shikimic acid (138-59-0) + N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine (35661-39-3) → {4-[(1S,2S,3S,4R,6R)-6-((S)-1-Carbamoyl-ethylcarbamoyl)-2,3,4-trihydroxy-cyclohexylsulfanyl]-2,3-dihydroxy-butylsulfanyl}-acetic acid tert-butyl ester

Conditions	Yield
Multistep reaction;

Upstream product

• 40227-25-6 cis-4,5-dihydroxy-1,2-dithiane 
• 930-22-3 epoxybutene 
• 564-00-1 1,2:3,4-Diepoxybutane 
• 1194723-61-9 Dithiothreitoltetraacetat 
• 16096-98-3 trans-1,2-dithiane-4,5-diol 

Downstream Products

• 115321-74-9 ((E)-(3S,4R)-3,4-Dihydroxy-1,6-dithia-cycloundec-9-en-8-yl)-(3-nitro-phenyl)-methanone 
• 14193-38-5 C₄H₈O₂S₂^(1-) 

Relevant academic research and scientific papers

Preparation method of 1, 4-dithiothreitol

The invention discloses a preparation method of 1, 4-dithiothreitol, and the method comprises the following steps of: carrying out oxidation reaction on 1, 4-disulfonic acid-2-butene serving as an initial raw material and an oxidant to obtain a first intermediate; hydrolyzing the first intermediate obtained in the S1 in alkali liquor to obtain a second intermediate; and carrying out reduction reaction on the second intermediate obtained in the S2 and a reducing agent to prepare the 1, 4-dithiothreitol. According to the method, 1, 4-disulfonic acid-2-butene is used as the initial raw material,the dithiothreitol is synthesized through the three steps of oxidation, hydrolysis and reduction, the preparation method is simple in process and high in yield, the yield is 77% or above, and the application performance of the obtained product is consistent with that of a conventional product.

Intermediate compound for synthesizing dithioerythritol, application of intermediate compound and synthesis method of dithioerythritol

The invention discloses an intermediate compound for synthesizing dithioerythritol, an application of the intermediate compound and a synthesis method of the dithioerythritol. The intermediate compound is 2, 3-diacetyl thiomethylethylene oxide, and the chemical formula of the intermediate compound is shown in the specification, and the intermediate compound can be prepared by performing substitution reaction on 2, 3-dibromomethylethylene oxide and thioacetate. The synthesis method of the dithioerythritol comprises the step of carrying out hydrolysis reaction on the intermediate compound. The 2, 3-diacetyl thiomethylethylene oxide can be directly hydrolyzed to obtain the dithioerythritol, the preparation of the 2, 3-diacetyl thiomethyl ethylene oxide is simple, a new synthesis idea is provided for the synthesis of the dithioerythritol, the synthesis route is short, the operation is simple and convenient, and the yield is high.

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.

METHOD FOR THE PRODUCTION OF BISEPOXIDES AND DITHIOLS

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Micellar systems

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Phosphine-assisted rearrangement of 4,5-dihydroxy-1,2-dithianes to 4-hydroxy-3-mercaptotetrahydrothiophenes

Treatment of 4,5-dihydroxy-1,2-dithianes with trialkylphosphines and triphenylphosphine under neutral and moderately basic conditions led to the efficient and stereospecific production of 4-hydroxy-3-mercaptotetrahydrothiophenes. The reaction is projected

4-hydroxyquinoline-3-carboxamides and hydrazides as antiviral agents

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Interleukin-2/viral antigen protein chimers

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BIOLOGICALLY ACTIVE COMPOUNDS ISOLATED FROM AEROBIC FERMENTATION OF TRICHODERMA VIRIDE

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Process for reconfiguring keratin fibre

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