Formation of Bis(hydroxyalkyl)N-nitrosamines as products of the nitrosation of spermidine Public Deposited

http://ir.library.oregonstate.edu/concern/graduate_thesis_or_dissertations/m900nw73d

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  • The purpose of this study was to characterize the nonvolatile, water soluble, bis(hydroxyalkyl)N-nitrosamines produced from the reaction of spermidine and nitrite. The biologically occurring polyamine spermidine was reacted with nitrite in the presence of acid. The reaction products were isolated and converted to trimethylsilyl (TMS) derivatives. The derivatized products were separated by gas-liquid chromatography using an all glass, wall coated, capillary column. Mass spectral data were collected on the chromatographic effluent. Four isomers of bis(hydroxyalkyl)N-nitrosamine were synthesized by combining the appropriate aminopropanol with the appropriate chlorobutanol. Infrared, nuclear magnetic resonance, mass spectral, and thin-layer chromatographic data were collected on the synthetic compounds to assure their structure. Kovat's indices were collected on the TMS derivative of each authentic compound and compared to the retention data collected on the TMS derivatives of the reaction products of spermidine and nitrite. A comparison of the mass spectra of the TMS derivatives of the authentic compounds to the spectra of the reaction products having the same retention time allowed structural assignments to four compounds. The compounds identified, in order of decreasing amounts were: 4-hydroxybutyl(3-hydroxypropyl)N-nitrosamine, 3-hydroxybutyl(3-hydroxypropyl)N-nitrosamine, 4-hydroxybutyl(2- hydroxypropylJN-nitrosamine, and 3-hydroxybutyl(2-hydroxypropyl)N-nitrosamine.
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