Synthesis of pyrraline reference material

Z Lebensm Unters Forsch. 1996 Jan;202(1):72-4. doi: 10.1007/BF01229689.

Abstract

A simplified and improved method is described for the preparation of pyrraline, a lysine derivative from the advanced Maillard reaction and potential indicator for heat treatment of foods. The compound was obtained in a high degree of purity and with a yield of 31% from N alpha-t-butyloxycarbonyl-L-lysine after heating with 3-deoxy-D-erythro-hexos-2-ulose for 2 h at 70 degrees C in the dry state, preparative fractionation of the resulting N alpha-t-butyloxycarbonyl pyrraline with reverse-phase liquid chromatography and final deprotection of the intermediate compound with acetic acid.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cooking
  • Food Analysis / standards*
  • Hot Temperature
  • Indicators and Reagents
  • Maillard Reaction*
  • Molecular Structure
  • Norleucine / analogs & derivatives*
  • Norleucine / analysis
  • Norleucine / chemical synthesis
  • Pyrroles / analysis*
  • Pyrroles / chemical synthesis*
  • Reference Standards

Substances

  • Indicators and Reagents
  • Pyrroles
  • 2-formyl-5-(hydroxymethyl)pyrrole-1-norleucine
  • Norleucine