Isolation and Characterization of a Coupled Compound of Thiamin with Catechol

Abstract

Equimolecular amounts of thiamin and catechol incubated under suitable conditions produced an unknown reaction product isolated as a light yellow powder from the reaction mixture by reverse-phase ODS column chromatography.
Elemental analysis of the purified powder showed the molecular formula to be C₁₈H₂₂N₄O₄S-HCl-H₂O in agreement with a molecular ion peak found at m/e 390 in the mass spectrum. These results together with the data of IR and NMR spectrometry possibly show that this material consists of an isomeric mixture of S-3, 4 and S-2, 3-dihydroxyphenylthiamin (I and II) which probably arise as a result of oxidative addition of the thiol group of thiamin to catechol.