86335-59-3

Basic information

• Product Name: purine-6-sulfenic acid
• Synonyms: purine-6-sulfenic acid
• CAS NO: 86335-59-3
• Molecular Formula: C5H4 N4 O S
• Molecular Weight: 168.18
• Mol File: 86335-59-3.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 624.3°C at 760 mmHg
• Flash Point: 331.4°C
• Appearance: /
• Density: 1.78g/cm³
• Vapor Pressure: 1.89E-16mmHg at 25°C
• Refractive Index: 1.827
• CAS DataBase Reference: purine-6-sulfenic acid(CAS DataBase Reference)
• NIST Chemistry Reference: purine-6-sulfenic acid(86335-59-3)
• EPA Substance Registry System: purine-6-sulfenic acid(86335-59-3)

Safety Data

• Hazardous Substances Data: 86335-59-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C5H4N4OS/c10-11-5-3-4(7-1-6-3)8-2-9-5/h1-2,10H,(H,6,7,8,9)

Upstream product

• 157930-09-1 6-Mercaptopurine 

Relevant articles and documents

Synthesis and pH-Dependent Stability of Purine-6-sulfenic Acid, a Putative Reactive Metabolite of 6-Thiopurine

Previous studies have shown that 6-thiopurine is metabolically activated by hepatic cytochrome P-450 to an intermediate capable of binding to proteins by a mixed disulfide linkage.The identity of the active metabolite was postulated to be purine-6-sulfenic acid.In the present report, we describe the synthesis of the sulfenic acid derivatives of 6-thiopurine and two structurally similar compounds, 9-methyl-6-thiopurine and 4-mercapto-1H-pyrazolopyrimidine.The unusual pH-dependent stability profiles of these compounds in buffered aqueous media are presented and explained on the basis of a disproportionation mechanism of sulfenic acid decomposition.Studies with radiolabeled purine-6-sulfenic acid demonstrate that this species binds directly to hepatic microsomal protein.These results support the proposed involvement of purine-6-sulfenic acid in the metabolic activation and tissue binding of 6-thiopurine.