Solvolysis of Pyridoxal Hydrochloride in Alcohols

Yoshiko Nagata, Reiko Yoda, Yoshikazu Matsushima

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

HPLC, 1H-NMR, MS and product analysis showed that pyridoxal hydrochloride was solvolyzed in methanol to form pyridoxal monomethylacetal. The reaction followed first order kinetics with the rate constant of 1.45 x 10-4 s-1 at 40 °C. The rate was not appreciably enhanced in the presence of an excess amount of HC1. The reaction was greatly retarded by addition of an equimolar amount of KOH. The results showed that the pyridinium-phenol species of pyridoxal hemiacetal is reactive. The reaction is responsible for the “aging” of alcoholic solutions of pyridoxal, which has caused poor reproducibility of the kinetic data for the formation of Schiff bases with amino acids.

Original languageEnglish
Pages (from-to)1019-1022
Number of pages4
JournalChemical and Pharmaceutical Bulletin
Volume41
Issue number6
DOIs
Publication statusPublished - 1993

Keywords

  • Keywords pyridoxal
  • acetal
  • aldimine
  • methanol
  • solvolysis

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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