64808-90-8

Basic information

• Product Name: 2-[bis(ethylsulfanyl)methyl]tetrahydrofuran-3,4-diol (non-preferred name)
• CAS NO: 64808-90-8
• Molecular Formula: C₉H₁₈O₃S₂
• Molecular Weight: 238.3674
• Mol File: 64808-90-8.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 402.2°C at 760 mmHg
• Flash Point: 197°C
• Density: 1.276g/cm³
• Vapor Pressure: 3.84E-08mmHg at 25°C
• Refractive Index: 1.582
• CAS DataBase Reference: 2-[bis(ethylsulfanyl)methyl]tetrahydrofuran-3,4-diol (non-preferred name)(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[bis(ethylsulfanyl)methyl]tetrahydrofuran-3,4-diol (non-preferred name)(64808-90-8)
• EPA Substance Registry System: 2-[bis(ethylsulfanyl)methyl]tetrahydrofuran-3,4-diol (non-preferred name)(64808-90-8)

Safety Data

• Hazardous Substances Data: 64808-90-8(Hazardous Substances Data)

Usage

Also known as

Dithiomaltol

Structure

Tetrahydrofuran ring with two ethylsulfanyl groups attached and a diol functional group

Potential applications

Chelating agent, antioxidant, and in other chemical processes
Considered a non-preferred name
Use may be limited due to sulfur content and potential toxicity

Upstream product

• 1114-34-7 D-lyxose 
• 6838-08-0 (2R,3S,4S)-5,5-bis(ethylthio)pentane-1,2,3,4-tetraol 

Relevant articles and documents

2,5-ANHYDRO-1-DEOXY-D-LYXITOL, 2,5-ANHYDRO-1-DEOXY-D-MANNITOL, AND 2,5-ANHYDRO-1-DEOXY-D-TALITOL. SYNTHESIS AND ENZYMIC STUDIES

2,5-Anhydro-1-deoxy-D-mannitol (4), 2,5-anhydro-1-deoxy-D-talitol (8), and 2,5-anhydro-1-deoxy-D-lyxitol (12) were prepared by Raney-nickel desulfurization of 2,5-anhydro-D-mannose dihexyl dithioacetal (3), 2,5-anhydro-D-talose dihexyl dithioacetal (7), and 2,5-anhydro-D-lyxose diethyl dithioacetal (11), respectively, in 64percent yield based on starting thioacetal.Compounds 3 and 7 were prepared in 42percent yield, by the acid-catalyzed condensation of 2,5-anhydro-D-mannose and 2,5-anhydro-D-talose, respectively, with hexanethiol.Compound 11 was prepared in 66percent yield, by treatment of D-lyxose diethyl dithioacetal with p-toluenesulfonyl chloride-pyridine.Compounds 4,8,and 12 were examined as substrates and inhibitors for yeast hexokinase and bovine-liver fructokinase.Hexokinase and fructokinase phosphorylated 4 with Km values of 25 and 1.94 mM, and Vmax (4)/Vmax (D-fructose) 0.007 and 0.13, respectively.Fructokinase was competitively inhibited by 8 and 12, with Ki values of 17 and 99 mM, respectively.