Metabolism of 2,4-dinitrotoluene and 2,6-dinitrotoluene, and their dinitrobenzyl alcohols and dinitrobenzaldehydes by Wistar and Sprague-Dawley rat liver microsomal and cytosol fractions

Chem Pharm Bull (Tokyo). 1989 Jul;37(7):1904-8. doi: 10.1248/cpb.37.1904.

Abstract

The metabolism of 2,4-dinitrotoluene (2,4-DNT), 2,4-dinitrobenzyl alcohol (2,4-DNB), 2,4-dinitrobenzaldehyde (2,4-DNBAl), 2,6-DNT, 2,6-DNB and 2,6-DNBAl in the microsomal and cytosol fractions prepared from unfortified male Wistar and male Sprague-Dawley (S.D.) rat livers was investigated. Data obtained by high-performance liquid chromatography (HPLC) indicated that the products of dinitrotoluenes (2,4-DNT and 2,6-DNT), dinitrobenzyl alcohols (2,4-DNB and 2,6-DNB), and dinitrobenzaldehydes (2,4-DNBAl and 2,6-DNBAl) in the microsomal and cytosol preparations containing nicotinamide adenine dinucleotide phosphate (NAD(P] and reduced NAD(P)(NAD(P)H) were dinitrobenzyl alcohols (2,4-DNB and 2,6-DNB), dinitrobenzaldehydes (2,4-DNBAl and 2,6-DNBAl), and dinitrobenzoic acids (2,4-DNBA and 2,6-DNBA), and dinitrobenzyl alcohols (2,4-DNB and 2,6-DNB), respectively. From these results, it was concluded that the dinitrobenzaldehydes (2,4-DNBAl and 2,6-DNBAl) were intermediates in the oxidations of dinitrobenzyl alchols (2,4-DNB and 2,6-DNB) to dinitrobenzoic acids (2,4-DNBA and 2,6-DNBA), and that the oxidations of dinitrobenzyl alcohols (2,4-DNB and 2,6-DNB) to dinitrobenzaldehydes (2,4-DNBAl and 2,6-DNBAl) and the reductions of dinitrobenzaldehydes to dinitrobenzyl alcohols (2,4-DNB and 2,6-DNB) were reversible.(ABSTRACT TRUNCATED AT 250 WORDS)

Publication types

  • Comparative Study

MeSH terms

  • Animals
  • Benzaldehydes / analysis
  • Benzyl Alcohols / analysis
  • Cytosol / metabolism*
  • Dinitrobenzenes / metabolism*
  • In Vitro Techniques
  • Male
  • Microsomes, Liver / metabolism*
  • Nitrobenzenes / metabolism*
  • Rats
  • Rats, Inbred Strains

Substances

  • Benzaldehydes
  • Benzyl Alcohols
  • Dinitrobenzenes
  • Nitrobenzenes
  • 2,4-dinitrotoluene
  • 2,6-dinitrotoluene