1119-62-6

Usage

Uses

Used in Chemical Synthesis:
3,3'-Dithiodipropionic acid is used as a precursor substrate in the synthesis of 3-mercaptopropionic acid-containing polythioesters. Its reactivity and structural properties make it a valuable component in creating these types of polymers.
Used in Electrochemistry:
In the field of electrochemistry, 3,3'-dithiodipropionic acid is employed to form self-assembled monolayers on a polycrystalline gold electrode. This results in the creation of a gold 3,3'-dithiodipropionic acid self-assembled monolayer modified electrode, which has potential applications in sensing and other electrochemical processes.
Used in Nanotechnology:
3,3'-Dithiodipropionic acid is used as a capping agent for introducing charge on gold nanoparticle surfaces. This application is crucial in the development of nanoparticles with specific properties and functionalities, which can be utilized in various industries, including electronics, medicine, and environmental science.
Used in Microbiology:
In the field of microbiology, 3,3'-dithiodipropionic acid is added as a primary carbon supplement in the culture medium of a novel betaproteobacterium, strain DPN7. This application highlights its role in supporting the growth and metabolism of specific microorganisms, which can be beneficial for biotechnological and environmental applications.
Overall, 3,3'-dithiodipropionic acid is a versatile compound with a wide range of applications across different industries, including chemical synthesis, electrochemistry, nanotechnology, and microbiology. Its unique properties and reactivity make it a valuable asset in the development of new materials, technologies, and biological processes.

Synthesis Reference(s)

Tetrahedron, 41, p. 2903, 1985 DOI: 10.1016/S0040-4020(01)96614-1Chemical and Pharmaceutical Bulletin, 34, p. 486, 1986 DOI: 10.1248/cpb.34.486

Upstream product

• 56-23-5 tetrachloromethane 
• 41345-70-4 3-acetylsulfanyl-propionic acid 
• 57-57-8 β-Propiolactone 
• 6302-95-0 xanthate carboxylic acid 
• 6414-69-3 ethyl 3-iodopropanoate 
• 292638-85-8 acrylic acid methyl ester 
• 447-31-4 Desyl chloride 
• 107-96-0 3-mercaptopropionic acid 
• 107106-61-6 3-propionic acid 
• 49670-47-5 3,4-Dihydro-4-oxo-1,2-benzoxathiin-2,2-dioxid 
• 1986-38-5 2-thioxo-[1,3]thiazinan-4-one 
• 156-57-0 2-mercaptoethylamine hydrochloride 
• 2127-03-9 2,2'-dipyridyldisulphide 
• 7553-56-2 iodine 

Downstream Products

• 15441-06-2 dimethyl 3,3'-dithiodipropionate 
• 4938-00-5 3-((carboxymethyl)thio)propanoic acid 
• 107-96-0 3-mercaptopropionic acid 
• 44826-45-1 3-sulfopropanoic acid 
• 1609-40-1 3,3'-Dithiobis(propansaeure-diethylester) 
• 29271-33-8 3-(trifluoromethylthio)propanoic acid 
• 167767-93-3 (S)-2-[4-(3-{2-[4-((S)-1,3-Bis-tert-butoxycarbonyl-propylcarbamoyl)-phenylcarbamoyl]-ethyldisulfanyl}-propionylamino)-benzoylamino]-pentanedioic acid di-tert-butyl ester 
• 105158-29-0 3,3-Dithiopropionic acid di-p-nitrophenyl ester 
• 196806-22-1 C₅₀H₅₂N₄O₁₀P₂S₂ 
• 57757-57-0 3,3'-dithiodipropionic acid, bis(succinimido) ester 

Relevant academic research and scientific papers

Vis/NIR light driven mild and clean synthesis of disulfides in the presence of Cu2(OH)PO4 under aerobic conditions

A highly efficient one-pot strategy has been developed for the synthesis of disulfide in the presence of air under the irradiation of Vis/NIR light. Copper hydroxyphosphate (CHP) Cu2(OH)PO4, has been used as a Vis/NIR active photocatalyst. Disulfide forms on the surface of the catalyst by a radical mechanism. The protocol is useful for solvent free disulfide synthesis from a variety of thiols. This journal is

Design and fabrication of dual-targeted delivery system based on gemcitabine-conjugated human serum albumin nanoparticles

Dual-targeted drug delivery system has established their reputation as potent vehicles for cancer chemotherapies. Herein, gemcitabine (Gem) was conjugated to human serum albumin (HSA) via dithiodipropionic anhydride to fabricate Gem-HSA nanoparticles. It was hypothesized that this system can enhance the low stability of Gem and can improve its intracellular delivery. Furthermore, folate was applied as targeting agent on HSA nanoparticles for increasing the tumor selectivity of Gem. To evaluate the structural properties of synthesized products, 1H NMR and FT-IR were performed. Moreover, HPLC was implemented for confirming the conjugation between HSA and Gem. Nanoparticles have shown spherical shape with negative charge. The release rate of Gem was dependent to the concentration of glutathione and pH. Folate-targeted HSA nanoparticles have shown higher cytotoxicity, cellular uptake, and apoptosis induction on folate receptor overexpressing MDA-MB-231 cells in comparison to non-targeted nanoparticles. Finally, it is considered that the developed dual-targeted nanoparticles would be potent in improving the stability and efficacy of intracellular delivery of Gem and its selective delivery to cancer cells.

Efficient and selective oxidation of thiols to disulfides by 1,4-diazabicyclo[2.2.2]octane-di-N-oxide-diperhydrate under neutral and heterogeneous conditions

1,4-Diazabicyclo[2.2.2]octane-di-N-oxide-di-perhydrate selectively oxidizes thiols to disulfides in acetonitrile in good yields. The method is generally useful for a wide variety of thiols.

Tribromoisocyanuric acid (TBCA) and oxone-MX systems as oxidizing agents: Oxidative coupling of thiols to their corresponding disulfides under mild and heterogeneous conditions

Tribromoisocyanuric acid (TBCA) and Oxone-MX systems were used as effective oxidizing agents for the oxidation of thiols to their corresponding disulfides under mild conditions at room temperature with good to excellent yields.

Photocatalytic transformation of organic and water-soluble thiols into disulfides and hydrogen under aerobic conditions using Mn(CO)5Br

The photolysis of Mn(CO)5Br with thiols under aerobic conditions at room temperature produces the corresponding disulfides in high yields, accompanied by the evolution of hydrogen as the only other product. This transformation is a greener route toward the synthesis of disulfides and exhibits 100% atom economy. The catalytic system possesses high chemoselectivity, as evidenced by high disulfide yields even in the presence of numerous functional groups. A mechanism has been proposed to involve free radical species and is based on fac-Mn(CO)3(RSH)2Br being an important catalytic intermediate. Mn(CO)5Br is also able to catalyze the conversion of naturally occurring water-soluble thiols such as cysteine and glutathione. Coupled with suitable enzymes that regenerate thiols from disulfides using proton sources, it is possible to envisage a combined catalytic cycle that is able to reduce protons to hydrogen efficiently.

Silica chloride/NaNO2 as a novel heterogeneous system for production of thionitrites and disulfides under mild conditions

Thiols can be readily converted to their corresponding thionitrites with a combination of silica chloride (I), wet SiO2 and sodium nitrite in dichloromethane at room temperature. Disulfides result from the homolytic cleavage of the sulfur-nitrogen bond of the unstable thionitrite and subsequent coupling of the resultant thiyl radicals.

Oxidation of thiols with metal nitrates supported on TAFF

Twelve thiols were readily oxidized to the corresponding disulfides by means of four metal nitrates supported on TAFF, a bentonitic clay, under mild conditions. However, in some cases, thioethers and other interesting by-products were detected. Some of the disulfides showed antimicotical activities against Aspergillus fumigatus, Aspergillus niger, Aspergillus candidus, Microsporum gypseum, Candida albicans, and Cryptococcus neoformans.

Oxidation of thiols to disulfides with molecular oxygen in subcritical water

Molecular oxygen is used as an efficient oxidant for the oxidative coupling of thiols to disulfides in subcritical water in the absence of catalysts. The procedure utilizes water and does not require support materials and metal salts providing high yields (>90%). Springer-Verlag 2006.

Poly(N-bromobenzene-1,3-disulfonylamide), N,N,N′,N′- tetrabromobenzene-1,3-disulfonylamide and DABCO-bromine complex: As novel reagents for the oxidative coupling of thiols to disulfides

An efficient method for the oxidative coupling of thiols to their corresponding disulfides by new reagents poly(N-bromobenzene-1,3- disulfonylamide) PBBS, N,N,N′,N′-tetrabromobenzene-1,3- disulfonylamide TBBDA and DABCO-bromine complex is described. The reaction was applicable to a variety of thiols with high chemoselectivity.

SERS surfaces modified with a 4-(2-pyridylazo)resorcinol disulfide derivative: Detection of copper, lead, and cadmium

We have developed a surface-enhanced Raman spectroscopic technique for the determination of Pb2+, Cd2+, and Cu2+ concentration using a 4-(2-pyridylazo)resorcinol (PAR) coating modified with a disulfide. The disulfide provided a strong anchor to a roughened silver substrate. Atomic specificity was demonstrated by the distinct spectral changes that occurred through the interaction of Pb2+, Cd2+, and Cu2+ ions with the indicator. The absorption of these metals by the coating was followed with SERS and could be fit to a Frumkin isotherm. Langmuirian behavior was not observed; this is most likely due to the electrostatic repulsions as the metal cations are absorbed. The detection limits at pH 6 for Pb2+, Cd2+, and Cu2+ were 522, 50.3, and 1.49 ppb, respectively. Flow experiments using an optical fiber probe indicated instantaneous response to changes in metal concentration.