Isolation and characterization of a coupled compound of thiamin with catechol.
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 X HCl X 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.
D002396:Catechols; D055598:Chemical Phenomena; D002621:Chemistry; D002627:Chemistry, Physical; D002845:Chromatography / Q000379:methods; D002851:Chromatography, High Pressure Liquid; D006863:Hydrogen-Ion Concentration; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D010084:Oxidation-Reduction; D013055:Spectrophotometry, Infrared; D013831:Thiamine
D002396:Catechols; C034221:catechol; D013831:Thiamine