Abstract
The increasing demand for healthier food products, with reduced levels of table salt, sugar, and mono sodium glutamate, reinforce the need for novel taste enhancers prepared by means of food-grade kitchen-type chemistry. Although several taste modulating compounds have been discovered in processed foods, their Maillard-type ex food production is usually not exploited by industrial process reactions as the yields of target compounds typically do not exceed 1–2%. Natural deep eutectic solvents (NADES) are reported for the first time to significantly increase the yields of the taste enhancers 1-deoxy-d-fructosyl-N-β-alanyl-l-histidine (49% yield), N-(1-methyl-4-oxoimidazolidin-2-ylidene) aminopropionic acid (54% yield) and N2-(1-carboxyethyl) guanosine 5′-monophosphate (22% yield) at low temperature (80–100 °C) within a maximum reaction time of 2 h. Therefore, NADES open new avenues to a “next-generation culinary chemistry” overcoming the yield limitations of traditional Maillard chemistry approaches and enable a food-grade Maillard-type generation of flavor modulators.
Highlights
The complex series of chemical reactions between reducing carbohydrates and free amino groups of proteins, peptides or amino acids that constitute the Maillard reaction is one of the most important sources for coloration of thermally treated foods, and for the formation of aroma and taste [1,2]
The objective of the present study was, to investigate for the first time the suitability of selected Natural deep eutectic solvents (NADES) systems to promote the ex food production of taste enhancers (2, 3, and 5) in comparison to current aqueous reaction systems, and to identify reaction conditions leading to increased yields of the target compounds
To better compare the yields of the Amadori product, generated in aqueous systems, with those in candidate NADES systems, first, the influence of the reaction time, temperature and the pH value was investigated in aqueous solution of carnosine and glucose
Summary
The complex series of chemical reactions between reducing carbohydrates and free amino groups of proteins, peptides or amino acids that constitute the Maillard reaction is one of the most important sources for coloration of thermally treated foods, and for the formation of aroma and taste [1,2]. Besides molecules that pronounce a characteristic odor in heated food, the Maillard reaction brings molecules that contribute to taste sensations such as bitterness [3,4], cooling effects [5,6] or umami-like taste [7], respectively. N-(1-Carboxyethyl)-6-(hydroxymethyl)pyridinium-3-ol inner salt (1; Figure 1), coined alapyridaine, has been reported as the first taste enhancing Maillard reaction product in beef broth, and was found to be thermally generated from alanine and glucose [12,13]. Derived from a Maillard-type carboxyethylation of guanosine 50 -monophosphate (50 -GMP) upon reaction with glyceraldehyde or dihydroxyacetone, respectively, the diastereomeric pair (R)- and (S)-N2 -(1-carboxyethyl)-guanosine 50 -monophosphate (2) was identified as potent umami taste enhancers in processed yeast extracts [16]. N-(1-methyl-4-oxoimidazolidin-2-ylidene) aminopropionic acid (3) was found to be generated upon carboxyethylation of creatine/creatinine
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