Browning reaction products, flavor

MaillardReaction (Nonenzymatic Glycation), Browned reaction products ate formed by heating amino acid and simple sugar. This reaction is important in food science relating to coloring, taste, and flavor enhancement (79), and is iUustrated as follows ... 

Non-enzymatic browning reactions play a central role in the formation of food aroma and flavor, especially in heat-treated foods. The purpose of this work is to present sensory data, scattered in the literature, for volatile non-enzymatic browning reaction products and related compounds. The compilation has no pretensions to completeness and only a small part of the extensive patent literature has been covered. Anyhow, it is felt that a compilation of this kind, which has not been available hitherto, would be useful to workers in the field. 

Thus, the potential role of DMHF as a flavor impact compound and as an intermediate to form additional flavor compounds in heat-abused citrus products should be carefully considered. 2,3-Dihydro-3,5-dihydroxy-6-methyl-4-H-pyran-4-one was also isolated from dehydrated orange juice (37) and is known as a novel nonenzymic browning reaction product. This pyranone has a high threshold value, over 200 ppm (38), and appears to possess negligible odor character. 

Flavor notes of products of amino compounds-sugars reaction were reviewed with emphasis on amino-ribose system. Meat-like flavor was imparted by browning reaction products of camosine-, citrul-line-, histidine-, glutamic-, 2-pyrrolidone-5-carboxylic-, methionine-, cysteine-, cysteic-, and taurine-ribose. Recent advancements in nitrogen-, oxygen- and sulfur hetercyclics and lipid browning were presented. 

Figure 9. Effects of browning reaction products for the autoxidation of potato chips at 50°C. Potatoes were sliced with deep-fat-fried in soybean oil with our without browning reaction products. Symbols are o — o, POV and o — o, CV of soybean oil in potato chips (control), — , POV and -—, CV of soybean oil browning reaction products (10%) in potato chips. Arrows indicate the development of oxidized flavor.

Mabrouk, A.F. Flavor of browning reaction products. In Food Taste Chemistry, Boudreau, J.C., Eds. ACS Symp. Ser. 115, American Chemical Society Washington D.C., 1979 pp 205-245. 

Bassette and Keeney (1960) ascribed the cereal-type flavor in dry skim milk to a homologous series of saturated aldehydes resulting from lipid oxidation in conjunction with products of the browning reaction. The results of Parks and Patton (1961) suggest that saturated and unsaturated aldehydes at levels near threshold may impart an off-flavor suggestive of staleness in dry whole milk. Wishner and Keeney (1963) concluded from studies on milk exposed to sunlight that C6 to Cn alk-2-enals are important contributors to the oxidized flavor in this product. Parks et al. (1963) concluded, as a result of quantitative carbonyl analysis and flavor studies, that alk-2-4-dienals, especially... 

Maiilard Reaction. In amino acids, the amino group tends to form condensation products with aldehydes. This reaction is regarded as the cause of the browning reaction when an amino acid and a sugar coexist. A characteristic flavor, useful in food preparations, is evolved along with the color in this reaction,... 

The sugars, which contribute much to the acceptability of citrus juices, under adverse conditions can play a major role in the formation of off flavors that reduce the acceptability of the citrus juices and their products. The sugars, primarily the hexoses, can participate in "browning" reactions that cause darkening of the juice and these reactions give rise to components that are described generally as apricot-like or pineapple-like in flavor. In general,the more processed flavor that a citrus product exhibits, the less acceptable it becomes to the consumer. 

The studies reviewed demonstrate that browning products produced on retorting of meat inhibit development of WOF, so that canned meat products are not subject to this flavor defect. The flavor of canned meat is less desirable, however, than that of freshly cooked meat. Nevertheless, the strong inhibitory action of the Maillard reaction products against WOF suggests that they could be useful in preventing development of WOF, so further research in this area could be fruitful. 

Heterocyclic compounds are primarily formed through non-enzymatic browning reactions. Recent studies of deep-fat fried food flavors led to the identification of pyrazines, pyridines, thiazole, oxazoles and cyclic polysulfides which had long-chain alkyl substitutions on the heterocyclic ring. The involvement of lipid or lipid decomposition products in the formation of these compounds could account for the long-chain alkyl substitutions. Model systems were used to study the participation of lipids in the formation of pyrazines, pyridines, thiophenes and cyclic polysulfides. 

A maltol-ammonia browning reaction produced thirteen pyrazines, two pyrroles, two oxazoles, and one pyridine (12). The major products of this system were 2-ethyl-3-hydroxy-6-methylpyridine and 2-ethyl-3,6-dimethylpyrazine. It is difficult to construct possible formation mechanisms for these compounds from maltol and ammonia. All the carbon atoms must come from maltol. It is possible, then, that maltol degrades into smaller carbon units and that these fragments recombine to form larger carbon units, producing these compounds. Recently, the formation of thiophenones and thiophenes from the reaction of 2,5-dimethyl-4-hydroxy-3(2H)-furanone and cysteine or cystine was reported (13. 14). All these reaction mixtures were reported to possess a cooked meat-like flavor. 

---