On the formation of reductic acid from pentoses or hexuronic acids

Ahmad, Tania; Andersson, Ronnie; Olsson, Kjell; Westerlund, Eric

doi:10.1016/0008-6215(93)84254-4

Cited by 9 publications

(7 citation statements)

References 8 publications

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“…Isbell proposed DHCP as the main precursor in the formation of reductic acid, 13 but Ahmad et al determined that DHCP is only an isomer but not a tautomer of reductic acid, and therefore there have to be different formation pathways. 14 We observed that DHCP is preferably formed at pH 3, but according to Ahmad et al 5 we also suppose that it is not the precursor or a tautomer of reductic acid but an alternative degradation product of Dgalacturonic acid.…”

Section: ■ Results and Discussionsupporting

confidence: 48%

d-Galacturonic Acid as a Highly Reactive Compound in Nonenzymatic Browning. 1. Formation of Browning Active Degradation Products

Bornik

Kroh

2013

J. Agric. Food Chem.

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Thermal treatment of an aqueous solution of D-galacturonic acid at pH 3, 5, and 8 led to rapid browning of the solution and to the formation of carbocyclic compounds such as reductic acid (2,3-dihydroxy-2-cyclopenten-1-one), DHCP (4,5-dihydroxy-2-cyclopenten-1-one), and furan-2-carbaldehyde, as degradation products in weak acidic solution. Studies on their formation revealed 2-ketoglutaraldehyde as their common key intermediate. Norfuraneol (4-hydroxy-5-methyl-3-(2H)-furanone) is a typical alkaline degradation product and formed after isomerization. Further model studies revealed reductic acid as an important and more browning active compound than furan-2-carbaldehyde, which led to a red color of the model solution. This red-brown color is also characteristic of thermally treated uronic acid solutions.

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Section: ■ Results and Discussionsupporting

confidence: 48%

d-Galacturonic Acid as a Highly Reactive Compound in Nonenzymatic Browning. 1. Formation of Browning Active Degradation Products

Bornik

Kroh

2013

J. Agric. Food Chem.

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“…Uronic acids are abundant in nature and consequently play a very important role in the formation of browning and volatile products in groceries. For d -galacturonic acid ( d -GalA), which is present in the backbone of the pectin molecule, a drastic influence on the color formation was already reported in several studies: e.g., Hodge et al − Uronic acids in general show a stronger browning potential in comparison to reducing sugars, such as d -galactose ( d -Gal). ,− It was observed that one of the major chromophore-developing substances in model systems of these sugar acids is reductic acid. It is formed after decarboxylation of d -GalA and further dehydration reactions that lead to the reactive α-ketoglutaraldehyde.…”

Section: Introductionmentioning

confidence: 94%

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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“…Three peaks migrating before the EOF, with m/z 113 (t m about 2.7 min), 175 (t m about 2.8 min) and 181 (t m about 2.7 min) were found. The peak with m/z 113 could correspond to 2,3-dihydroxycyclopent-2-en-1-one (reductic acid), as it has been shown to originate from pentoses and hexuronic acids [36,37]. The peak with m/z 175 could be glucuronolactone, although in alkaline medium, the equilibrium between lactone and the parent straight-chain hydroxy acid is shifted towards the acid form (see peak with m/z 193 below).…”

Section: Application To Aged Papersmentioning

confidence: 99%

Capillary electrophoresis with electrospray ionisation-mass spectrometry for the characterisation of degradation products in aged papers

Dupont¹,

Seemann²,

Lavédrine³

2012

Talanta

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A methodology for capillary electrophoresis/electrospray ionisation mass spectrometry (CE/ESI-MS) was developed for the simultaneous analysis of degradation products from paper among two families of compounds: low molar mass aliphatic organic acids, and aromatic (phenolic and furanic) compounds. The work comprises the optimisation of the CE separation and the ESI-MS parameters for improved sensitivity with model compounds using two successive designs of experiments. The method was applied to the analysis of lignocellulosic paper at different stages of accelerated hygrothermal ageing. The compounds of interest were identified. Most of them could be quantified and several additional analytes were separated.

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On the formation of reductic acid from pentoses or hexuronic acids

Cited by 9 publications

References 8 publications

d-Galacturonic Acid as a Highly Reactive Compound in Nonenzymatic Browning. 1. Formation of Browning Active Degradation Products

d-Galacturonic Acid as a Highly Reactive Compound in Nonenzymatic Browning. 1. Formation of Browning Active Degradation Products

Formation of Phenolic Compounds from d-Galacturonic Acid

Capillary electrophoresis with electrospray ionisation-mass spectrometry for the characterisation of degradation products in aged papers

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