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Mass spectrometric characterization of some human metabolites of flumecinol
Author(s) -
Tamás József,
Mák Marianna,
Klebovich Imre,
Vereczkey László,
Tóth Edit
Publication year - 1988
Publication title -
biomedical and environmental mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 0887-6134
DOI - 10.1002/bms.1200150407
Subject(s) - chemistry , electron ionization , mass spectrum , hydroxylation , trifluoromethyl , primary (astronomy) , molecule , mass spectrometry , characterization (materials science) , silylation , molecular mass , ionization , stereochemistry , organic chemistry , medicinal chemistry , computational chemistry , chromatography , alkyl , enzyme , ion , nanotechnology , physics , materials science , astronomy , catalysis
The mass spectrometric behaviour of six human metabolites formed by hydroxylation in various positions of the α‐ethyl group or/and on the phenyl ring of 3‐trifluoromethyl‐α‐ethyl‐benzyhydrol (flumecinol) and seven related compounds has been studied. The electron impact mass (EI) spectra of these compounds show significant and characteristic effects of substituents, but many of them suffer from weakness or even from absence of the M + ˙ peak owing to the very facile primary loss of the α‐aliphatic chain, i.e. no direct information can be obtained about the size of the molecule and that of this chain. It is demonstrated for derivatives possessing a hydroxylated α‐ethyl group that the difficulties in structural characterization due to the lack or weakness of M + ˙ and [M + H] + peaks in their EI and chemical ionization mass spectra, respectively, can be overcome by studying their silylated or boronated derivatives. Furthermore, silylation enables us to obtain a clear base for distinction of the primary and secondary alcohols of this type.