4775-93-3

Usage

Uses

Used in Pharmaceutical Industry:
2,2'-Dithiodipropionic acid is used as a pharmaceutical ingredient for its antioxidant properties, which can be beneficial in the development of medications that require protection against oxidative stress.
Used in Personal Care Products:
In the personal care industry, 2,2'-dithiodipropionic acid is used as an ingredient in cosmetic and skincare products, where its ability to form disulfide bonds can contribute to the formulation's stability and effectiveness.
Used in Rubber Industry:
2,2'-Dithiodipropionic acid is used as a curing agent in the rubber industry, where it helps in the cross-linking process that strengthens the rubber material, enhancing its durability and performance.
Despite its extensive use, it is important to handle 2,2'-dithiodipropionic acid with caution due to potential health and environmental hazards associated with its use.

InChI:InChI=1/C6H10O4S2/c1-3(5(7)8)11-12-4(2)6(9)10/h3-4H,1-2H3,(H,7,8)(H,9,10)

Upstream product

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• 1206518-35-5 3-[(2R,3S)-1-hydroxy-2,4-dimethylpentan-3-yl]-5-methyl-thiazolidine-2,4-dione 
• 1206518-32-2 3-[(1S,2S)-3-hydroxy-2-methyl-1-phenylpropyl]-5-methyl-thiazolidine-2,4-dione 
• 1206518-34-4 3-[(2S,3S)-4-hydroxy-3-methyl-1-phenylbutan-2-yl]-5-methylthiazolidine-2,4-dione 
• 1206518-38-8 3-[(2S,3R)-4-hydroxy-3-methyl-1-phenylbutan-2-yl]-5-methylthiazolidine-2,4-dione 

Downstream Products

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• 21793-77-1 (+)-2,2'-dithiobispropionic acid 
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• 7783-06-4 hydrogen sulfide 
• 64-19-7 acetic acid 
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• 1313496-28-4 C₁₈H₃₂N₂O₆S₂ 
• 1313496-26-2 C₁₄H₂₄N₂O₆S₂ 
• 1313496-30-8 C₁₄H₂₄N₂O₈S₂ 
• 1822-43-1 2,2'-disulfanediyl-bis-propionyl chloride 

Relevant academic research and scientific papers

METAL-CATALYZED OXIDATIVE COUPLING OF THIOLS

Disclosed are methods for preparing disulfide compounds through oxidative coupling of thiol compounds. Thiols are oxidized to the corresponding disulfide compound in high yield in presence of a base and a metal salt. The method uses low catalyst loadings and provides organic disulfide compounds with little to no byproducts.

METHODS OF TREAT1NG CANCER AND OTHER DISEASES

Disclosed are a method of treating cancer in a cell, a method of enhancing the chemotherapeutic treatment of a cancer treatment agent, a method of reducing resistance of a cancer cell to a chemotherapeutic agent, a method of reducing the amount or activity of an ABC-family mRNA and/or protein, a method of reducing the amount or activity of the ABCB1 mRNA and/or protein or the ABCC1 mRNA and/or protein in an animal cell undergoing cancer treatment, a method of reducing the amount or activity of glutathione and/or Bcl2 in the cancer cell, a method of treating other multidrug resistant diseases, and a method of treating a multidrug resistant cell such as a bacterial multidrug resistant Staphylococcus aureus (MRSA), tuberculosis, fungal infection, or MDR malaria, by administering a compound of the Formula (I): a diastereoisomer thereof, or a pharmaceutically acceptable salt thereof, wherein R1-R4 are as described herein. Also disclosed are pharmaceutical compositions comprising a compound of formula (I), a diastereoisomer thereof, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier

RETRACTED ARTICLE: Collateral sensitivity of multidrug-resistant cells to the orphan drug tiopronin

A major challenge in the treatment of cancer is multidrug resistance (MDR) that develops during chemotherapy. Here we demonstrate that tiopronin (1), a thiol-substituted N-propanoylglycine derivative, was selectively toxic to a series of cell lines expressing the drug efflux pump P-glycoprotein (P-gp, ABCB1) and MRP1 (ABCC1). Treatment of MDR cells with 1 led to instability of the ABCB1 mRNA and consequently a reduction in P-gp protein, despite functional assays demonstrating that tiopronin does not interact with P-gp. Long-term exposure of P-gp-expressing cells to 1 sensitized them to doxorubicin and paclitaxel, both P-gp substrates. Treatment of MRP1-overexpressing cells with tiopronin led to a significant reduction in MRP1 protein. Synthesis and screening of analogues of tiopronin demonstrated that the thiol functional group was essential for collateral sensitivity while substitution of the amino acid backbone altered but did not destroy specificity, pointing to future development of targeted analogues. This article not subject to U.S. Copyright. Published 2011 by the American Chemical Society.

Rearrangement of oxazolidinethiones to thiazolidinediones or thiazinanediones and their application for the synthesis of chiral allylic ureas and α-methyl-β-amino acids

A novel rearrangement has been found between oxazolidinethiones and acyl halides under N-acylation reaction conditions to afford N-substituted 2,4-thiazolidinediones and N-substituted 1,3-thiazinane-2,4-diones. These heterocycles were used for the synthesis of chiral allylic ureas and α-methyl-β-amino acids.

Oxidation of some thioacids by tetraethylammonium chlorochromate: A kinetic and mechanistic study

The oxidation of thioglycollic, thiolactic and thiomalic acids by tetraethylammonium chlorochromate (TEACC) is first order both in TEACC and thioacids. The reaction is catalysed by hydrogen ions. The hydrogen ion dependence has taking the form : kobs = a + b [H+]. The oxidation of thiolactic acid has been studied in nineteen different organic solvents. The solvent effect has been analysed by using Kamlet's and Swain's multiparametric equations. A mechanism involving the formation of a thioester and its decomposition in slow step has been proposed.

Kinetics and mechanism of oxidation of some thioacids by morpholinium chlorochromate

Oxidation of thioglycollic, thiolactic and thiomalic acids by morpholinium chlorochromate is first order both in MCC and thioacids. The reaction is catalysed by hydrogen ions. The hydrogen ion dependence takes the form k obs=a+b [H+]. Oxidation of the thiolactic acid has been studied in nineteen different organic solvents. The solvent effect has been analysed by using Kamlet's and Swain's multiparametric equations. A mechanism involving the formation of a thioester and its decomposition in slow step is also proposed.

Kinetics and mechanism of oxidation of some thioacids by benzyltrimethylammonium chlorobromate

The oxidation of some thioacids, viz., thioplycollic, thiolactic and thiomalic acids by benzyltrimethylammonium chlorobromate (BTMACB) has been studied in acetic acid. The reaction is first order with respect to BTMACB. Michaelis-Menten type of 'kinetics have been observed with respect to the reductants. The reaction has been studied in solvents of different compositions of acetic acid and water. The solvent composition effect has been analysed using Grunwald-Weinstein equation. A mechanism involving the formation of an intermediate complex in the pre-equilibrium and its subsequent decomposition in slow step has been proposed.

Dynamic kinetic resolution of amines involving biocatalysis and in situ free radical mediated racemization

(Chemical Equation Presented) The association of lipase-catalyzed enzymatic resolution with in situ racemization mediated with the thiyl radical enables the dynamic kinetic resolution of non-benzylic amines. It leads to (R)-amides with high enantioselectivities. It can be applied either to the conversion of racemic mixtures or to the inversion of (S)-enantiomers.

Kinetics and mechanism of the oxidation of some thioacids by tetrabutylammonium tribromide

The oxidation of some thioacids viz. thioglycollic, thiolactic and thiomalic acids by tetrabutylammonium tribromide (TBATB) has been studied in acetic acid. The reaction is first order with respect to TBATB. Michaelis-Menten type of kinetics were observed with respect to the reductants. The reaction has been studied in solvents of different compositions of acetic acid and water. The solvent composition effect has been analysed using Grunwald-Weinstein equation. A mechanism involving the formation of an intermediate complex in the pre-equilibrium and its subsequent decomposition in slow step has been proposed.

Kinetics and mechanism for reduction of the anticancer prodrug trans,trans,trans-[PtCl2(OH)2(c-C6H11NH2)(NH3)] (JM335) by thiols.

The reduction of the platinum(IV) prodrug trans,trans,trans-[PtCl2(OH)2(c-C6H11NH2)(NH3)] (JM335) by L-cysteine, DL-penicillamine, DL-homocysteine, N-acetyl-L-cysteine, 2-mercaptopropanoic acid, 2-mercaptosuccinic acid, and glutathione has been investigated at 25 degrees C in a 1.0 M aqueous perchlorate medium with 6.8 a reductive elimination process through an attack by sulfur at one of the mutually trans chloride ligands, yielding trans-[Pt(OH)2(c-C6H11NH2)(NH3)] and RSSR as the reaction products, as confirmed by 1H NMR. Second-order rate constants for the reduction of JM335 by the various protolytic species of the thiols span more than 3 orders of magnitude. Reduction with RS- is approximately 30-2000 times faster than with RSH. The linear correlation log(kRS) = (0.52 +/- 0.06)-pKRSH--(2.8 +/- 0.5) is observed, where kRS denotes the second-order rate constant for reduction of JM335 by a particular thiolate RS- and KRSH is the acid dissociation constant for the corresponding thiol RSH. The slope of the linear correlation indicates that the reactivity of the various thiolate species is governed by their proton basicity, and no significant steric effects are observed. The half-life for reduction of JM335 by 6 mM glutathione (40-fold excess) at physiologically relevant conditions of 37 degrees C and pH 7.30 is 23 s. This implies that JM335, in clinical use, is likely to undergo in vivo reduction by intracellular reducing agents such as glutathione prior to binding to DNA. Reduction results in the immediate formation of a highly reactive platinum(II) species, i.e., the bishydroxo complex in rapid protolytic equilibrium with its aqua form.