Synthesis of isothiocyanate-derived mercapturic acids
article
Twelve mercapturic acids derived from saturated and unsaturated aliphatic and aromatic isothiocyanates were synthesised, by adding isothiocyanate to a solution of N-acetyl-L-cysteine and sodium bicarbonate, in a typical yield of 77%. Isothiocyanates were synthesised first by adding the corresponding alkyl bromide to phthalimide potassium salt. The obtained N-alkyl-phthalimide was hydrazinolysed yielding the alkyl amine, which subsequently was reacted with thiophosgene yielding the isothiocyanate with an overall yield of 16%. Mercapturic acids in urine can serve as a biomarker of intake to determine the health promoting potential of isothiocyanates present in cruciferous vegetables. © 2003 Éditions scientifiques et médicales Elsevier SAS. All rights reserved.
Topics
Analytical researchBiomarkerGlucosinolatesIsothiocyanatesMercapturic acidsNucleophilic additionAcetylcysteineAcetylcysteine derivativeAmineBicarbonateBiological markerIsothiocyanic acid derivativePhosgenePhthalimide derivativeSynthesisVegetableAcetylcysteineBiological MarkersChromatography, High Pressure LiquidDietGlucosinolatesHumansIsothiocyanatesMagnetic Resonance SpectroscopyMass SpectrometryThiocyanatesVegetables
TNO Identifier
237161
ISSN
02235234
Source
European Journal of Medicinal Chemistry, 38(7-8), pp. 729-737.
Pages
729-737
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