2,5-Dihydroxy-1,4-dithiane

Chemical properties

white to yellowish crystalline powder

Chemical properties

2,5-Dihydroxy-1,4-dithiane has a sulfurous, meaty, toasted bread-like odor

The Uses of 2,5-Dihydroxy-1,4-dithiane

1,4-Dithiane-2,5-diol is a hydroxylated dithiane derivative with phytogrowth-inhibitory and antibacterial activities.

The Uses of 2,5-Dihydroxy-1,4-dithiane

1,4-Dithiane-2,5-diol was used in the synthesis of:

• substituted tetrahydrothiophene derivatives
• 2-amino-3-(arylsulfonyl)thiophenes, potential antiviral and antitumor agents

Definition

ChEBI: 1,4-Dithiane-2,5-diol is a member of dithianes.

Aroma threshold values

Aroma characteristics at 0.1% EtoH: sulfurous, grilled meaty, pungent, brothy, eggy, heavy and rich, toasted bread, tomato

Taste threshold values

Taste characteristics at 0.25 to 10 ppm: metallic, meaty savory chicken and beef, sulfurous, egg-yolk-like

Synthesis Reference(s)

Synthetic Communications, 14, p. 483, 1984 DOI: 10.1080/00397918408059569

General Description

1,4-Dithiane-2,5-diol undergoes bifunctional squaramide catalyzed sulfa-Michael/aldol cascade reaction with chalcones to afford trisubstituted tetrahydrothiophenes. It participates in diastereoselective [3+3] cycloaddition with azomethine imines catalyzed by 1,4-diazabicyclo[2.2.2]octane. It is a mercaptoacetaldehyde dimer and an efficient synthon for incorporating a thiol group to in situ generated nitroalkenes.