Volatile Chemicals Formed in the Headspace of a Heated D-Glucose/L-Cysteine Maillard Model System

Umano, Katsumi; Hagi, Yukio; Nakahara, Kazuaki; Shyoji, Akihiro; Shibamoto, Takayuki

doi:10.1021/jf00056a046

Cited by 61 publications

(48 citation statements)

References 19 publications

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“…Numerous sulphur containing heterocycles were formed from the precursors (93 compounds were identified in a heated cysteine-glucose mixture), which would otherwise react to form pyrazines [32]. Our results were similar to those reported in extruded wheat flour containing the added cysteine [33,34].…”

Section: Composition Of the Pyrazine Fractionsupporting

confidence: 88%

Effect of amino acids on the composition and properties of extruded mixtures of wheat flour and glucose

Farouk

Pudil

Janda

et al. 2000

Nahrung

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Wheat flour was extruded at 100-120 degrees C with 5% D-glucose or mixtures of 5% D-glucose and 0.5% or 2.0% of L-alanine, L-leucine, L-lysine, L-threonine or L-cysteine. The extent of browning was only moderate, and yellow and red pigments were produced. The odour intensity increased with the addition of either glucose or a mixture of glucose and amino acids; the odour was not significantly intensive according to sensory acceptancy analysis. The odour profile was influenced by the structure of amino acid present in the extruded material. The addition of D-glucose increased the production of furan derivatives, and in lesser degree, of pyrazines in the extruded product. The pyrazine content increased with the addition of amino acids, except cysteine which enhanced the production of sulphur compounds instead of pyrazines. The composition of the pyrazine fraction varied depending on the amino acid added. Pretreatment of D-glucose with an amino acid in aqueous solution affected the composition of volatiles, but it did not significantly enhance the pyrazine production.

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Section: Composition Of the Pyrazine Fractionsupporting

confidence: 88%

Effect of amino acids on the composition and properties of extruded mixtures of wheat flour and glucose

Farouk

Pudil

Janda

et al. 2000

Nahrung

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“…Dry heating of L-cysteine systems seems to favour the formation of thiazolines. Umano et al (1995) observed 2-methylthiazolidine as the major volatile in a dry-heated L-cysteine/glucose mixture, although this most probably has only a minor impact on the flavour. Possibly it is formed via a reaction of the intermediate acetaldehyde with cysteamine originating from L-cysteine decarboxylation.…”

Section: The Maillard Reaction Of Cysteinementioning

confidence: 94%

The role of sulfur chemistry in thermal generation of aroma

Cerny

2015

Flavour Development, Analysis and Perception in Food and Beverages

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“…Acetaldehyde derived from cysteine in the Maillard reaction (Vernin and Metzger 1981; Vernin and others 1992; Perez Locas and Yaylayan 2004) has been postulated as the source of the C(2) fragment in the thermal degradation of cysteine alone (Shu and others 1985). Cysteine alone at 180 °C for 2 h gave mostly 2‐methylthiazolidine and measurable amounts of 2‐ethylthiazolidine, 2‐methylthiazole, 2‐ethylthiazole, 2‐methyl‐2‐thiazoline among other heterocyclic products (Umano and others 1995). In another thermal study, cysteine alone gave 2‐methylthiazole, 2‐methyl‐2‐thiazoline, and 2‐methylthiazolidine.…”

Section: Introductionmentioning

confidence: 99%

The Cysteine Reaction with Diacetyl under Wine‐Like Conditions: Proposed Mechanisms for Mixed Origins of 2‐Methylthiazole, 2‐Methyl‐3‐thiazoline, 2‐Methylthiazolidine, and 2,4,5‐Trimethyloxazole

Marchand¹,

Almy²,

Revel³

2011

Journal of Food Science

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A part of the "bouquet of wines" can be caused by the presence of odorous heterocycles produced by chemical reactions between S-amino acids and α-dicarbonyl compounds. Under wine ageing physic-chemical conditions (20 ± 2 °C, ethanol/water 12% v/v, pH 3.5), products of the diacetyl (DI) reaction with cysteine include a number of 1,3-N,S and 1-3-N,O 5 member heterocycles having methyl groups attached at C(2). The origin of this methyl-C(2) fragment was not clear; it could be supplied from DI or from cysteine. To explore this question, a parallel reaction was run in which DI was replaced by 3,4-hexanedione. With the C(1) and C(4) carbons of DI thus marked with methyl groups, the product distribution demonstrated that in the DI and cysteine reaction, both DI and cysteine provided the methyl-C(2) to varying degrees in the formation of 2-methylthiazole, 2-methyl-3-thiazoline and 2,4,5-trimethyloxazole but only cysteine supplied this fragment for 2-methylthiazolidine. The results are interpreted in terms of reaction paths appropriate for the mild conditions. These pathways shed light on the mechanisms leading from dicarbonyls to heterocyclic compounds. Like all the chemical pathways, they anticipate the impact of other compounds and physicochemical parameters on heterocyclic generations the generation of heterocyclics. They also suggest the presence of unexplored odorous compounds.

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Volatile Chemicals Formed in the Headspace of a Heated D-Glucose/L-Cysteine Maillard Model System

Cited by 61 publications

References 19 publications

Effect of amino acids on the composition and properties of extruded mixtures of wheat flour and glucose

Effect of amino acids on the composition and properties of extruded mixtures of wheat flour and glucose

The role of sulfur chemistry in thermal generation of aroma

The Cysteine Reaction with Diacetyl under Wine‐Like Conditions: Proposed Mechanisms for Mixed Origins of 2‐Methylthiazole, 2‐Methyl‐3‐thiazoline, 2‐Methylthiazolidine, and 2,4,5‐Trimethyloxazole

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