Key Aspects of Amadori Rearrangement Products as Future Food Additives.

Yue Luo,Shiming Li,Chi-Tang Ho

doi:10.3390/molecules26144314

Abstract

Flavor is one of the most important factors in attracting consumers and maximizing food quality, and the Maillard reaction (MR) is highly-involved in flavor formation. However, Maillard reaction products have a big drawback in their relatively low stability in thermal treatment and storage. Amadori rearrangement products (ARPs), MR intermediates, can alternatively act as potential flavor additives for their better stability and fresh flavor formation ability. This review aims to elucidate key aspects of ARPs’ future application as flavorings. The development of current analytical technologies enables the precise characterization of ARPs, while advanced preparation methods such as synthesis, separation and drying processes can increase the yield of ARPs to up to 95%. The stability of ARPs is influenced by their chemical nature, pH value, temperature, water activity and food matrix. ARPs are associated with umami and kokumi taste enhancing effects, and the flavor formation is related to amino acids/peptides of the ARPs. Peptide-ARPs can generate peptide-specific flavors, such as: 1,6-dimethy-2(1H)-pyrazinone, 1,5-dimethy-2(1H)-pyrazinone, and 1,5,6-trimethy-2(1H)-pyrazinone. However, further research on systematic stability and toxicology are needed.

Highlights

The Maillard reaction has been one of the most important reactions in flavor generation since its first discovery by French chemist Louis-Camille Maillard in 1912 [1]
The Schiff base goes through Amadori rearrangement with a nucleophilic catalyst and forms a more stable 1-amino-1-deoxy-2ketose, called Amadori rearrangement products (ARPs) [2]
The stability of ARPs is influenced by their chemical nature, pH value, temperature, water activity and food matrix

Summary

Introduction

The Maillard reaction has been one of the most important reactions in flavor generation since its first discovery by French chemist Louis-Camille Maillard in 1912 [1]. The Schiff base goes through Amadori rearrangement with a nucleophilic catalyst and forms a more stable 1-amino-1-deoxy-2ketose, called Amadori rearrangement products (ARPs) [2]. While ARPs are specific for a Schiff base derived from aldose sugar, Heyns rearrangement products (HRPs, 2-amino2-deoxyaldose) are derived from ketose sugar [3]. The Maillard reaction is commonly seen in thermally processed food with attractive and complex flavors, such as bread, cereal, coffee, roasted meat. These flavors mainly come from the formation of pyrazines, pyrroles, alkylpyridines, acylpyridines, furanones, furans, oxazoles, and thiophenes [5].

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