Gaschromatographisch-massenspektrometrische Untersuchung der im Modellsystem Cystein/Methionin/Furfural unter R�stbedingungen gebildeten Aromastoffe

Silwar, Reinhard; Tressl, Roland

doi:10.1007/bf01028064

Cited by 25 publications

(8 citation statements)

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“…This compound is likely to be formed from the selfcondensation of 2-furfural (Shibamoto 1977). The remaining dimeric furans identified (apart from 5-(2-furfuryl)-2-furfural) have also been reported in model systems containing 2-furfural as an initial reactant (Shibamoto 1977;Silwar and Tressl 1989) and it seems likely that they are formed from 2-furfural in this study. However, some compounds were identified in greater amounts from the pH 5.0 system.…”

Section: Dimeric Furansmentioning

confidence: 78%

“…2-Furfural may itself act as a precursor for at least some of the Type I11 furans. For example, 2-acetylfuran has been identified among the reaction products of a model system of 2-furfural, hydrogen sulphide and ammonia (Shibamoto 1977) and, together with 5-methyl-2furfural, in a 2-furfural-cysteine-methionine mixture (Silwar and Tressl 1989). The second explanation for a lower yield of Type I11 furans in the isolate prepared from the pH 5.0 system is that some of the compounds formed may have taken part in further reactions to give non-volatile compounds, some of which may be col-oured.…”

Section: Monocyclic Furansmentioning

confidence: 99%

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Xylose‐lysine model systems: The effect of pH on the volatile reaction products

Apriyantono

Ames

1993

J Sci Food Agric

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Aqueous molal solutions of xylose and lysine (initial pH 4.9) were refluxed either with control of the pH at 5.0 or without pH control (final pH 2.6). Analysis by gas chromatography (GC) and GC-mass spectrometry resulted in the identification of 58 and 28 compounds, respectively, from the two systems. Furans were the main reaction products in both systems and 2-furfural alone comprised 522 and 999 g kg-' of the volatiles, respectively, from the systems with final pH values of 5.0 and 2.6. Maintaining the pH at 5.0 resulted in a higher yield and greater numbers of nitrogen-containing compounds, and monocyclic pyrroles, pyridines and 2,3-dihydro-1 H-pyrrolizines were identified only in that system. Aliphatic compounds, alicyclic compounds, benzene derivatives, 1-(2-furfury1)pyrroles and pyrazines were also identified. This investigation is the first report of the formation of 2,3-dihydro-lH-pyrrolizines in a model system containing lysine as the amino compound ; a possible mechanism is proposed.

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Section: Dimeric Furansmentioning

confidence: 78%

Section: Monocyclic Furansmentioning

confidence: 99%

Xylose‐lysine model systems: The effect of pH on the volatile reaction products

Apriyantono

Ames

1993

J Sci Food Agric

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“…Studies on the cysteine−ribose model reaction have elucidated that furfural (aldehyde) is considered to be involved in the formation of FFT and MFT through its reaction with either hydrogen sulfide or sulfur-containing amino acids ( , ). Recently quantitative studies, using stable isotope dilution analysis, confirmed that FFT is indeed the major product formed during thermal treatment of furfural in the presence of cysteine ().…”

Section: Introductionmentioning

confidence: 99%

Furfural−Cysteine Model Reaction in Food Grade Nonionic Oil/Water Microemulsions for Selective Flavor Formation

Yaghmur

Aserin

Garti

2002

J. Agric. Food Chem.

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The thermal reaction between cysteine and furfural was investigated at 65 degrees C in five-component food grade oil/water (O/W) microemulsions of R-(+)-limonene/ethanol, EtOH/water/propylene glycol, PG/Tween 60 as apart of a systematic study on the generation of aroma compounds by utilizing structured W/O and O/W fluids. The furfural-cysteine reaction led to the formation of unique aroma compounds such as 2-furfurylthiol (FFT), 2-(2-furanyl)thiazolidine (main reaction product), 2-(2-furanyl)thiazoline, and N-(2-mercaptovinyl)-2-(2-furanyl)thiazolidine. These products were determined and characterized by GC-MS. Enhancement in flavor formation is termed "microemulsion catalysis". The chemical reaction occurs preferably at the interfacial film, and therefore a pseudophase model was assumed to explain the enhanced flavor formation. The product internal composition is dictated by process conditions such as temperature, time, pH, and mainly the nature of the interface. Increasing water/PG ratio leads to a dramatic increase in the initial reaction rate (V(0)). V(0) increased linearly as a function of the aqueous phase content, which could be due to the increase in the interfacial concentration of furfural. Microemulsions offer a new reaction medium to produce selective aroma compounds and to optimize their formation.

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“…The thiols shown in Figure 1 are formed by the Maillard reaction of cysteine and might contribute to the flavors of heated foods and beverages, due to their low odor thresholds (Whitfield et al, 1992). Actually, 2-methyl-3-furanthiol (MFT) and 2-furfurylthiol (FFT) have been detected as character impact odorants of roasted coffee (Tressl, 1981(Tressl, , 1989(Tressl, , 1990Tressl et al, 1983;Holscher et al, 1990;Blank et al, 1992), cooked meat Grosch, 1988, 1990a;Farmer and Patterson, 1991;Grosch and Zeiler-Hilgart, 1992), and wheat bread (Baltes and Song, 1994).…”

Section: Introductionmentioning

confidence: 99%

“…It is well-known that thiols oxidize easily to disulfides. For this reason it is not surprising that the 15 disulfides or mixed disulfides (Table 1) resulting from the oxidation of the 5 thiols listed in Figure 1 have been identified in commercial meat flavorings (Gasser and Grosch, 1990b;Ruther and Baltes, 1994a,b) as well as in model Maillard reaction systems (Tressl et al, 1983(Tressl et al, , 1990Hartmann et al, 1984;Reineccius and Liardon, 1985;Silwar and Tressl, 1989;Farmer and Mottram, 1990;Gu ¨ntert et al, 1990Gu ¨ntert et al, , 1992aWerkhoff et al, 1990;Zhang and Wo, 1991;Farmer and Patterson, 1991;Whitfield et al, 1992;Mottram and Whitfield, 1994;Hofmann and Schieberle, 1995). FFT-FFT and MFT-MFT (nomenclature in Table 1) were found in cooked meat Grosch, 1988, 1990a;Farmer and Patterson, 1991;Grosch and Zeiler-Hilgart, 1992), and FFT-FFT was found in roasted coffee (Tressl, 1981) as well as in wheat bread (Baltes and Song, 1994).…”

Section: Introductionmentioning

confidence: 99%

Model Studies on the Oxidative Stability of Odor-Active Thiols Occurring in Food Flavors

Hofmann

Schieberle

Grosch

1996

J. Agric. Food Chem.

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Dilute ethereal solutions of mercaptoacetone (MA), 2-mercapto-3-butanone (MB), 3-mercapto-2pentanone (MP), 2-methyl-3-furanthiol (MFT), and 2-furfurylthiol (FFT), either alone or in pairs, were stored at 6 °C. During a period of 10 days the oxidation of the thiols to the corresponding disulfides or mixed disulfides was followed by high-resolution gas chromatography/mass spectrometry. In diethyl ether MFT showed the highest oxidation rate, which decreased in the order MFT . MA > MB ) MP ) FFT. After 1 day, mixed disulfides (e.g. MFT-FFT, FFT-MB) were detectable when pairs of the five thiols dissolved in diethyl ether were stored at 6 °C. MFT oxidized more slowly in dichloromethane than in diethyl ether, and it was stable in pentane. However, a heat treatment increased the oxidation rate of MFT dissolved in dichloromethane or pentane.

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Gaschromatographisch-massenspektrometrische Untersuchung der im Modellsystem Cystein/Methionin/Furfural unter R�stbedingungen gebildeten Aromastoffe

Cited by 25 publications

References 16 publications

Xylose‐lysine model systems: The effect of pH on the volatile reaction products

Xylose‐lysine model systems: The effect of pH on the volatile reaction products

Furfural−Cysteine Model Reaction in Food Grade Nonionic Oil/Water Microemulsions for Selective Flavor Formation

Model Studies on the Oxidative Stability of Odor-Active Thiols Occurring in Food Flavors

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