On the formation of 2,3-dihydroxyacetophenone from pentoses or hexuronic acids

Ahmad, Tania; Andersson, Ronnie; Olsson, Kjell; Theander, Olof

doi:10.1016/0008-6215(93)84253-3

Cited by 6 publications

(10 citation statements)

References 6 publications

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“…The occurrence of α-ketoglutaraldehyde was postulated in 1944 by Isbell and proven by Bornik. , Accordingly, higher concentrations of 6 can be measured in uronic acid model systems. This assumption is supported by considerations of Ahmad et al, who postulated a possible formation mechanism for 2,3-dihydroxyacetophenone in which an unsaturated aldehyde reacts with acetol . Both products occur during the degradation of d -GalA.…”

Section: Resultsmentioning

confidence: 66%

“…α-Ketoglutaraldehyde, in particular, moves into focus, since it is one of the compounds that is not found during the degradation of hexoses and is found only in very small concentrations in pentoses . Ahmad et al postulated a formation pathway that uses an unsaturated aldehyde and an enediol as educts, similar to those of 6 . These degradation intermediates of d -GalA can also be found in the postulated formation mechanisms of norfuraneol and furfural, which underscores the aforementioned assumption.…”

Section: Resultsmentioning

confidence: 99%

“…They assumed that the polyphenolic compounds may have an influence on the formation of color within the model systems but did not explore the matter further. Later, the same group postulated that the phenolic compounds were intermediates of the temperature-induced degradation of uronic acids and that unsaturated aldehydes take part in their formation mechanism …”

Section: Introductionmentioning

confidence: 99%

“…Later, the same group postulated that the phenolic compounds were intermediates of the temperature-induced degradation of uronic acids and that unsaturated aldehydes take part in their formation mechanism. 9 The aim of the present paper is to attempt a more in depth analysis of the reaction variety of uronic acids. GC-MS measurements were conducted to reveal the product spectrum and kinetics during the heat treatment of D-GalA and oligo-or polymer representatives, such as pectin and polygalacturonic acid, under different reaction conditions.…”

Section: ■ Introductionmentioning

confidence: 99%

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Formation of Phenolic Compounds from d-Galacturonic Acid

Urbisch

Einhorn-Stoll

Kastner

et al. 2018

J. Agric. Food Chem.

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Aqueous D-galacturonic acid (D-GalA) model systems treated at 130 °C at different pH values show an intense color formation, whereas other reducing sugars, such as D-galactose (D-Gal), scarcely react. GC-MS measurements revealed the presence of several phenolic compounds: e.g., 3,8-dihydroxy-2-methyl-4H-chromen-4-one (chromone) and 2,3-dihydroxybenzaldehyde (2,3-DHBA). These phenolic compounds, especially 2,3-DHBA, possess an intense browning potential and cannot be found within heated model solutions of reducing sugars. Investigations regarding the formation of these substances show that α-ketoglutaraldehyde plays an important role as an intermediate product. In addition, MS analysis of model systems of norfuraneol in combination with 2,3-DHBA showed the formation of oligomers that could also be detected in D-GalA model systems, leading to the assumption that, in addition to reductic acid, these compounds are jointly responsible for the strong color formation during the heat treatment of D-GalA.

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Section: Resultsmentioning

confidence: 66%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

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Formation of Phenolic Compounds from d-Galacturonic Acid

Urbisch

Einhorn-Stoll

Kastner

et al. 2018

J. Agric. Food Chem.

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“…The heat treatment of aqueous model systems of d -galacturonic acid, for example, resulted in browning that was 10 times higher than that of d -galactose or d -arabinose. − The higher reactivity of d -galacturonic acid during heat treatment, compared to neutral sugars, leads to the formation of several degradation products. These products include furfural and norfuraneol, which are also generated during the degradation of reducing sugars like d -galactose or d -glucose, as well as 2-furoic acid, 5-formyl-2-furoic acid, and reductic acid, which are specific to uronic acids. ,− …”

Section: Introductionmentioning

confidence: 99%

Influence of the Carboxylic Function on the Degradation of d-Galacturonic Acid and Its Polymers

Fatouros

Einhorn-Stoll

Kastner

et al. 2021

J. Agric. Food Chem.

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Past investigations have shown high browning potential during the caramelization of sugar acids in comparison to reducing sugars. However, no approaches to elucidate the chemical mechanisms have been made. Therefore, this study aims to clarify the reasons for the high browning potential by measuring the mutarotation velocity and the elimination of CO2 during the heat treatment of uronic acids. Performed polarimetric experiments show that the mutarotation velocity of d-galacturonic acid exceeds that of d-galactose by a factor of nearly 4.5. However, the ring opening velocity is not the only parameter that differs between the two carbohydrate structures. Measurements of the release of CO2 of heated d-galacturonic acid at 60 °C show a steady increase, and after 48 h, 6% of degraded d-galacturonic acid has eliminated CO2. CO2 release was also found during the heating of pectin, indicating a decarboxylation reaction during thermal degradation. One of the degradation reactions postulated for the release of CO2 leads to α-ketoglutaraldehyde, which is responsible for the formation of several chromophoric substances.

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