Title
Synthesis of isothiocyanate-derived mercapturic acids
Author
Vermeulen, M.
Zwanenburg, B.
Chittenden, G.J.F.
Verhagen, H.
Publication year
2003
Abstract
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.
Subject
Packaging
Analytical research
Biomarker
Glucosinolates
Isothiocyanates
Mercapturic acids
Nucleophilic addition
acetylcysteine
acetylcysteine derivative
amine
bicarbonate
biological marker
isothiocyanic acid derivative
phosgene
phthalimide derivative
article
synthesis
vegetable
Acetylcysteine
Biological Markers
Chromatography, High Pressure Liquid
Diet
Glucosinolates
Humans
Isothiocyanates
Magnetic Resonance Spectroscopy
Mass Spectrometry
Thiocyanates
Vegetables
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DOI
https://doi.org/10.1016/s0223-5234(03)00141-7
TNO identifier
237161
ISSN
0223-5234
Source
European Journal of Medicinal Chemistry, 38 (7-8), 729-737
Document type
article