Preparation of 1-Amino-1-deoxyfructose Derivatives by Stepwise Increase of Temperature in Aqueous Medium and Their Flavor Formation Compared with Maillard Reaction Products

Abstract

A novel method of Maillard reaction performed under stepwise increase of temperature was proposed for the preparation of Maillard reaction intermediate (MRI) derived from fructose (Fru) and phenylalanine (Phe). The optimal formation conditions of MRI in aqueous medium were determined as follows: pH 7.4 and heating for 100 min at 100 °C. The purified MRI was characterized to be 1-amino-1-deoxyfructose derivative (C₁₅H₂₁NO₇, 327 Da) by mass spectrometry and NMR. The methodological effectiveness of this new developed method was further verified. Although almost similar types of volatile compounds were identified in the three heated solutions of Fru-Phe mixture, Maillard reaction products (MRPs) and 1-amino-1-deoxyfructose derivatives, the concentration of total volatile compounds was 118.30 μg/L relative to the internal standard for Fru-Phe mixture and increased by 64.49 and 1024.64 μg/L for MRPs and 1-amino-1-deoxyfructose derivative, respectively. The results showed that more fresh flavors were controlled formed from 1-amino-1-deoxyfructose derivative compared with those from MRPs or Fru-Phe mixture during the subsequent heating treatment; thus, the 1-amino-1-deoxyfructose derivatives could be a great potential substitute of unstable MRPs or Fru-Phe mixture in preparation of flavoring.