Heyns compound

When the carbonyl compound is a ketose (e.g. fructose) rather than an aldose, the fructosylamine precursor (an N-alkyl fructoside) undergoes a Heyns rearrangement to form a 2-alkylamino-2-deoxy-D-glucose (15). These Heyns compounds are precursors of the browning phenonema. 

Retroaldolisation of the Heyns compound or a-cleavage of 1-DH can give acetaldehyde, which could lead to ethylmethyl or ethyldimethylpyrazines, but significant amounts of these were not observed however, see Rizzi.237... 

The origin of meat flavor has been shown to arise from the combination of two primary sources. The first is the tissue fat, both extracellular and intracellular, which produces carbonyl and other lipid and lipid-oxidation products. The fat component of meat flavor is viewed as being responsible for the species specific flavor in meat (9). The second major component of meat flavor is the lean portion. The proteins, peptides, and amino acids of the lean, add not only to the muscle food s general meaty flavor, but also undergo Maillard reactions with sugars to produce Amadori and Heyns compounds having meat flavor characteristics. 

Amino acids react readily with aldoses and ketoses upon heating to yield l-(N-carboxyalkyl(aryl)-amino)-l-deoxy-2-keto-D-hexoses (Amador1 compounds) and 2-(N-carboxyalkyl(aryl)-amino)-2-deoxy-aldo-D-hexoses (Heyns compounds), respectively (Paulsen... 

Amadori compounds with different amino acid residues have been detected in many heated and stored foods, e. g., in dried fruit and vegetables, milk products, cocoa beans or soy sauce. Amadori compounds are also found in the blood serum, especially of patients suffering from Diabetes mel-litus. As secondary amino acids, Amadori and Heyns compounds can be analytically detected by amino acid analysis (cf. protein section). 

As in the case of the deoxyosones, the concentrations of Amadori and Heyns compounds vary, depending on the reaction conditions (pH value, temperature, time, type and concentration of the educts). As a result, there is a change in the product spectrum and, consequently, in the color, taste, odor, and other properties of the food in each case. 

Wong MW (2003) Quantum-Chemical Calculations of Sulfur-Rich Compounds. 231 1-29 Wrodnigg TM, Eder B (2001) The Amadori and Heyns Rearrangements Landmarks in the History of Carbohydrate Chemistry or Unrecognized Synthetic Opportunities 215 115-175 Wyttenbach T, Bowers MT (2003) Gas-Phase Confirmations The Ion Mobility/Ion Chromatography Method. 225 201-226... 

The first group contains compounds produced in the early stages of the reaction by the breakdown of the Amadori or Heynes intermediates, and includes similar compounds to those found in the caramelisation of sugars. Many of these compounds possess aromas that could contribute to food flavour, but they are also important intermediates for other compounds. The second group comprises simple aldehydes, hydrogen sulphide or amino compounds that result from the Strecker degradation occurring between amino acids and dicarbonyl compounds. 

The complete diagram has not been worked out, but E. Heyn and 0. Bauer discussed the diagram for the case of a system of two elements, A and R, which form two compounds, Vj and V2> which give a complete homogeneous series of solid soln. y. V is supposed to boil without decomposition at 6, while V2 does not boil without... 

Only recently have N -nitroso Amadori compounds been characterized chemically. The first description of an -nltroso derivative of an Amadori compound reported the formation of 1-deoxy-l-(N -nitroso-3,4-xylidino)-D-f ructose to confirm that a secondary amino group had been formed in an Amadori compound ( 6). Coughlin et al. ( 7) and Heyns et al. ( 8) described the formation of nitrosated Amadori compounds. Since Amadori compounds are weakly basic secondary amines and occur widely in Maillard browned foods and beverages ( 5) and unburned tobacco ( ), the genotoxic potential of these compounds is of interest. 

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