| Summary: | 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. === Graduation date: 1977
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