38521-06-1

Basic information

• Product Name: 2-Mercaptopyrazine
• Synonyms: 2-Mercaptopyrazine;pyrazine-2(1H)-thione;2-Mercaptopyrazine 97% (HPLC)
• CAS NO: 38521-06-1
• Molecular Formula: C₄H₄N₂S
• Molecular Weight: 112.15
• Product Categories: API intermediates;Pyrazines
• Mol File: 38521-06-1.mol
• Article Data: 13

Chemical Properties

• Melting Point: 207-213°C
• Boiling Point: 191.3oC at 760 mmHg
• Flash Point: 69.5oC
• Appearance: /
• Density: 1.3g/cm3
• Vapor Pressure: 0.519mmHg at 25°C
• Refractive Index: 1.662
• Storage Temp.: 2-8°C
• PKA: 8.44±0.20(Predicted)
• CAS DataBase Reference: 2-Mercaptopyrazine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Mercaptopyrazine(38521-06-1)
• EPA Substance Registry System: 2-Mercaptopyrazine(38521-06-1)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 38521-06-1(Hazardous Substances Data)

Usage

General Description

2-Mercaptopyrazine is a chemical compound with a molecular formula C4H6N2S. It is a heterocyclic organic compound that contains both nitrogen and sulfur atoms in its structure. 2-Mercaptopyrazine is commonly used as a flavoring agent in the food and beverage industry, adding a savory, roasted, and nutty aroma. It is also used as an additive in the production of perfumes and fragrances, providing a unique and distinctive odor. Additionally, it has been studied for its potential use in pharmaceutical applications, specifically for its antimicrobial and antioxidant properties. Overall, 2-Mercaptopyrazine is a versatile chemical with various applications in different industries.

InChI:InChI=1/C4H4N2S/c7-4-3-5-1-2-6-4/h1-3H,(H,6,7)

Upstream product

• 14508-49-7 2-chloropyrazin 
• 147032-16-4 2-(4-Methoxybenzylthio)pyrazine 

Downstream Products

• 96129-41-8 2-(2-phenylethynyl)pyrazine 
• 164352-89-0 2-(allylthio)pyrazine 
• 21948-70-9 2-(methylthio)pyrazine 

Relevant articles and documents

Metalation of t-Butyl Sulfoxides, Sulfones and Sulfonamides of Pyridazine and Pyrazine. Metalation of Diazines. XX

In the pyridazine series, the use of tert-butylsulfinyl and tert-butylsulfonyl as ortho directing groups for metalation has been tested. Various functionalized products were obtained in good yields. In the case of 3-tert-burylsulfinyl-6-methoxypyridazine, the metalation was regioselective in ortho to the sulfinyl group. The metalation of 2-tert-butylsulfinyl and 2-tert-butylsulfonylpyrazine gave low to moderate yields. Synthesis of diazinesulfonamides were improved and the metalation of N-tert-butylsulfonamidopyrazine was achieved.

Inhibition of lipopolysaccharide-induced inducible nitric oxide synthase expression by a novel compound, mercaptopyrazine, through suppression of nuclear factor-kappaB binding to DNA

Macrophage cells in response to cytokines and endotoxins produced a large amount of nitric oxide (NO) by expression of inducible nitric oxide synthase (iNOS), resulting in acute or chronic inflammatory disorders including septic hypotension and atherosclerosis. In the present study, we investigated the effect and the mechanism of mercaptopyrazine (MP) in the induction of iNOS and NO production as a culminating factor for several inflammatory disorders. Pretreatment of MP alleviated the mortality of endotoxemic mice receiving a lethal bolus of lipopolysaccharide (LPS), which was associated with the reduced levels of serum nitrite/nitrate and IL-1β. In RAW264.7 mouse macrophage cells, MP (300 μM) inhibited both protein and mRNA levels of iNOS stimulated by LPS/interferon-γ (IFNγ) up to 50%. The nuclear factor-kappa B (NF-κB)-driven transactivation was also suppressed by MP to the same degree. Treatment of MP reduced the binding of NF-κB to the oligonucleotides containing NF-κB consensus sequence, while it did not affect the translocation of NF-κB to nuclear. Suppression of NF-κB activity by MP was completely reversed by a reducing agent, dithiothreitol, implying that MP might oxidize the sulfhydryl group(s) of DNA binding domain of NF-κB. In conclusion, MP would be one of interesting candidates or chemical moieties of iNOS expression inhibitor via specific suppression of NF-κB binding to DNA, and be useful as a chemopreventive agent or a therapeutic against iNOS-associated inflammatory diseases.

IMPROVED MODULATORS OF HEC1 ACTIVITY AND METHODS THEREFOR

Compounds, compositions, and methods for modulation of Hec1/Nek2 interaction are provided. Such compounds disrupt Nek2/Hec1 binding and may be useful as chemotherapeutic agents for neoplastic diseases