Characterization of Volatile Compounds from the Reaction of 3-Hydroxy-2-butanone and Ammonium Sulfide Model System

Abstract

The reactions between 3-hydroxy-2-butanone and ammoniun sulfide at 25, 50, 75, 100, 125, and 150 degrees C were studied. Four well-known flavor compounds, 2,4,5-trimethyloxazole, 2,4, 5-trimethyl-3-oxazoline, 2,4,5-trimethylthiazole, and 2,4, 5-trimethyl-3-thiazoline, were identified. Another four interesting intermediate compounds, 2-(1-hydroxyethyl)-2,4, 5-trimethyl-3-oxazoline, 2-(1-mercaptoethyl)-2,4, 5-trimethyl-3-oxazoline, 2-(1-hydroxyethyl)-2,4, 5-trimethyl-3-thiazoline, and 2-(1-mercaptoethyl)-2,4, 5-trimethyl-3-thiazoline, were also identified by GC-EIMS and GC-CIMS. All these intermediate compounds were formed at 25 degrees C. On the other hand, tetramethylpyrazine was the major product with a reaction temperature higher than 100 degrees C.

Effect of fermentation and postcooking procedure on quality parameters and volatile compounds of beef jerky

“…The I‐F group contained higher acetoin levels than those of all other groups ( p < .001), likely because lactic acid bacteria in starter cultures can produce acetoin via pyruvate metabolism (Montanari et al, 2016). Acetoin can form at low temperatures (e.g., 80°C) and react with ammonia to form heterocyclic aroma compounds (Liu, Liu, He, Song, & Chen, 2015; Xi, Huang, & Ho, 1998). Levels of 2,3‐octanedione were highest in the N‐F group ( p < .001) due to pyruvate metabolism in the starter culture (Montanari et al, 2016).…”

Generation of Acetoin and Its Derivatives in Foods

“…10 If sulfide is present in acetoin/ammonium reaction systems, similar sulfur-containing heterocyclic compounds will be produced. 80 HE-TM-oxazoline was manifested to be relatively unstable, and TTMP would be the main product either under an elevated reaction temperature 79 or in a prolonged storage time. 78 The dynamics of TTMP and its precursors during the industrial production process of a Chinese vinegar were investigated using GC-MS. 73 The results indicated that the main precursor of TTMP, that is, acetoin, was accumulated in the fermentation process, and then it condensed to TTMP during the subsequent storage period.…”

“…Le Quéré et al also hypothesized a chemical synthesis route of 2-alkyl-2,4,5-trimethyl-2,5-dihydrooxazole homologues in cheese from the precursors including acetoin, ammonia, and methyl ketones, which are abundant in cheeses . If sulfide is present in acetoin/ammonium reaction systems, similar sulfur-containing heterocyclic compounds will be produced …”

Influence of Deamidation on the Formation of Pyrazines and Proline-Specific Compounds in Maillard Reaction of Asparagine and Proline with Glucose

“…For example, the formation pathway of oxazolines and thiazolines was revealed via model reaction of 3-hydroxy-2-butanone and ammonium sulfide. 3 Schieberle used the Carbon Module Labeling (CAMOLA) technique in model systems to identify transient intermediates in the formation of Maillard flavor products. 4 Overall, Maillard model reactions offer a significant way to achieve varieties of flavor compounds and specific desired flavors.…”

“…However, specific flavor compounds or intermediates derived from Maillard reaction could also be involved in the model system. For example, the formation pathway of oxazolines and thiazolines was revealed via model reaction of 3-hydroxy-2-butanone and ammonium sulfide . Schieberle used the Carbon Module Labeling (CAMOLA) technique in model systems to identify transient intermediates in the formation of Maillard flavor products .…”