3H-1,2-Dithiole-3-thione

Base Information

• Chemical Name: 3H-1,2-Dithiole-3-thione
• CAS No.: 534-25-8
• Molecular Formula: C3H2S3
• Molecular Weight: 134.247
• Hs Code.: 2930909090
• European Community (EC) Number: 208-595-0
• UNII: WT2QF220RR
• DSSTox Substance ID: DTXSID7037052
• Nikkaji Number: J150.687K
• Wikidata: Q26840878
• NCI Thesaurus Code: C63644
• Metabolomics Workbench ID: 47016
• ChEMBL ID: CHEMBL368700
• Mol file: 534-25-8.mol

Synonyms:1,2-dithiol-3-thione;1,2-dithiole-3-thione;3H-1,2-dithiole-3-thione;D3T compound

Chemical Property of 3H-1,2-Dithiole-3-thione

Chemical Property:

• Vapor Pressure: 0.0763mmHg at 25°C
• Melting Point: 79-81°C
• Refractive Index: 1.806
• Boiling Point: 235.5 °C at 760 mmHg
• Flash Point: 96.2 °C
• PSA: 88.57000
• Density: 1.56g/cm³
• LogP: 2.53910
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 133.93186358
• Heavy Atom Count: 6
• Complexity: 94.2

Purity/Quality:

99% ^*data from raw suppliers

3H-1,2-Dithiole-3-thione ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CSSC1=S
• General Description: 3H-1,2-Dithiole-3-thione, also known as 1,2-dithiole-3-thione, is a heterocyclic compound featuring a five-membered ring with two sulfur atoms and a thione group. It serves as a key moiety in hydrogen sulfide (H2S)-releasing compounds, such as ADT-COOH, which exhibit antioxidant properties and neuroprotective effects by mitigating oxidative stress and enhancing dopamine levels, as demonstrated in Parkinson's disease models. 3H-1,2-Dithiole-3-thione's ability to release H2S in a controlled manner makes it valuable for therapeutic applications targeting neurodegenerative conditions. 3H-1,2-Dithiole-3-thione is a biologically active scaffold that contributes to the controlled release of H2S, offering potential therapeutic benefits in reducing oxidative stress and supporting dopaminergic neuron function.

Technology Process of 3H-1,2-Dithiole-3-thione

There total 12 articles about 3H-1,2-Dithiole-3-thione which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 69.6%

malonaldehydebis(dimethylacetal) (102-52-3) → 1,2-dithiole-3-thione (534-25-8)

Guidance literature:

With pyridine; sulfur; tetraphosphorus decasulfide; at 130 ℃;

DOI:10.1021/acs.jafc.9b06360

Reference yield: 58.0%

carbon disulfide (75-15-0,12122-00-8) + acetylene (74-86-2,25067-58-7) → 1,2-dithiole-3-thione (534-25-8)

Guidance literature:

acetylene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 0.5h;

carbon disulfide; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 1h;

With sulfur; isopropylamine; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 1h;

DOI:10.1016/j.tetlet.2014.07.104

Reference yield: 52.0%

1,4-di(n-propyl)tetrasulfane (52687-98-6) → 1,2-dithiole-3-thione (534-25-8)

Guidance literature:

at 350 ℃;

upstream raw materials:

propene

dipropyl trisulfide

1,4-di(n-propyl)tetrasulfane

malonaldehydebis(dimethylacetal)

Refernces

Controlled release of hydrogen sulfide significantly reduces ROS stress and increases dopamine levels in transgenic: C. elegans

10.1039/c9cc05153h

The study focuses on the controlled release of hydrogen sulfide (H2S), an endogenous signaling molecule with antioxidant properties that can ameliorate dopaminergic neuronal degeneration, particularly in Parkinson's disease models. The researchers designed and synthesized novel peptide constructs that self-assemble into nanostructures in aqueous medium and release H2S in a controlled manner. The chemicals used in the study include 2-(2-methoxy-4-(5-thioxo-5H-1,2-dithiol-3-yl)phenoxy)acetic acid (ADT-COOH), which contains an H2S-releasing dithiolethione (DTT) moiety, and aromatic dipeptides such as Phe-Phe, Dopa-Phe, and Trp-Trp. These peptides were conjugated with ADT-COOH to form conjugates I, II, and III, respectively. The purpose of these chemicals was to create peptide-based self-assembled structures that could serve as delivery systems for H2S, with the aim of reducing oxidative stress and increasing dopamine levels in transgenic Caenorhabditis elegans (C. elegans), a model organism used to study human diseases. The study demonstrated that these conjugates could significantly reduce ROS-induced oxidative stress and enhance dopamine levels, with conjugate III showing the most promising effects.