669-90-9

Basic information

• Product Name: 2-oxogluconic acid
• Synonyms: 2-oxogluconic acid;D-Arabino-2-hexulosonic acid;2-Oxo-2-deoxy-D-gluconic acid;2-Oxo-D-gluconic acid;2-dehydro-D-gluconic acid
• CAS NO: 669-90-9
• Molecular Formula: C₆H₁₀O₇
• Molecular Weight: 194.1394
• EINECS: 211-574-9
• Mol File: 669-90-9.mol
• Article Data: 10

Chemical Properties

• Melting Point: 152 °C
• Boiling Point: 528.6°C at 760 mmHg
• Flash Point: 225°C
• Appearance: /
• Density: 1.941g/cm³
• Vapor Pressure: 2.21E-13mmHg at 25°C
• Refractive Index: 1.663
• PKA: 2.10±0.54(Predicted)
• CAS DataBase Reference: 2-oxogluconic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-oxogluconic acid(669-90-9)
• EPA Substance Registry System: 2-oxogluconic acid(669-90-9)

Safety Data

• Hazardous Substances Data: 669-90-9(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
2-oxogluconic acid is used as a versatile building block in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and specialty chemicals. Its ability to undergo a wide range of chemical reactions, such as oxidation, reduction, and condensation, makes it a valuable starting material for the production of complex molecules.
Used in Analytical Chemistry:
2-oxogluconic acid is employed as a reagent in analytical chemistry for the determination of metal ions, particularly transition metals, through the formation of colored complexes. This property allows for the development of sensitive and selective methods for metal ion analysis in various samples.
Used in Food Industry:
In the food industry, 2-oxogluconic acid is used as a flavor enhancer and a precursor for the synthesis of other food additives. Its ability to chelate metal ions can also improve the stability and shelf life of food products by preventing oxidation and spoilage.
Used in Environmental Applications:
2-oxogluconic acid can be utilized in environmental applications, such as the bioremediation of heavy metal-contaminated soils and water. Its metal-chelating properties enable the sequestration and removal of toxic metal ions, thus reducing their environmental impact.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-oxogluconic acid is used as an active pharmaceutical ingredient or as an intermediate in the synthesis of various drugs. Its unique chemical properties and ability to form complexes with metal ions make it a promising candidate for the development of new therapeutic agents.
Used in Material Science:
2-oxogluconic acid can be employed in the development of novel materials, such as metal-organic frameworks (MOFs) and coordination polymers, which have potential applications in gas storage, catalysis, and sensing. Its ability to form stable coordination complexes with metal ions contributes to the formation of these advanced materials.

InChI:InChI=1/C6H10O7/c7-1-6(12)4(9)2(8)3(13-6)5(10)11/h2-4,7-9,12H,1H2,(H,10,11)/t2-,3+,4+,6?/m1/s1

Upstream product

• 57-48-7 D-Fructose 
• 643-71-0 D-glucosone 
• 32746-79-5 δ-D-mannonolactone 
• 90-80-2 D-Glucono-1,5-lactone 
• 2280-44-6 D-Glucose 
• 526-95-4 gluconic acid 
• 2595-33-7 2,5-diketo-D-gluconic acid 
• 7732-18-5 water 
• 7782-50-5 chlorine 
• 50-99-7 D-glucose 
• 7664-93-9 sulfuric acid 
• 7722-84-1 dihydrogen peroxide 
• 492-62-6 alpha-D-glucopyranose 
• 453-17-8 D-Glyceraldehyde 

Downstream Products

• 21063-40-1 D-arabino-[2]hexulosonic acid methyl ester 
• 89-65-6 isoascorbic acid 
• 50-81-7 ascorbic acid 
• 13529-17-4 5-Formyl-2-furancarboxylic acid 
• 3646-68-2 D-glucosaminic acid 
• 127-17-3 2-oxo-propionic acid 

Relevant articles and documents

Expanding the reaction space of aldolases using hydroxypyruvate as a nucleophilic substrate

Aldolases are key biocatalysts for stereoselective C-C bond formation allowing access to polyoxygenated chiral units through direct, efficient, and sustainable synthetic processes. The aldol reaction involving unprotected hydroxypyruvate and an aldehyde offers access to valuable polyhydroxy-α-keto acids. However, this undescribed aldolisation is highly challenging, especially regarding stereoselectivity. This reaction was explored using, as biocatalysts, a collection of aldolases selected from biodiversity. Several enzymes that belong to the same pyruvate aldolase Pfam family (PF03328) were found to produce the desired hexulosonic acids from hydroxypyruvate and d-glyceraldehyde with complementary stereoselectivities. One of them was selected for the proof of concept as a biocatalytic tool to prepare five (3S,4S) aldol adducts through an eco-friendly process.

Monosaccharide-H2O2 reactions as a source of glycolate and their stimulation by hydroxyl radicals

An analysis of the H2O2-induced breakdown and transformation of different keto-monosaccharides at physiological concentrations reveals that glycolate and other short-chained carbohydrates and organic acids are produced. Depletion of monosaccharides and glycolate synthesis occurs at increased rates as the length of the carbohydrate chain is decreased, and is significantly increased in the presence of trace amounts of Fe2+ ions (10 μM). Rates of monosaccharide depletion (initial concentration of 3 mM) observed were up to 1.55 mmol h-1 in the case of fructose, and 2.59 mmol h-1 in the case of dihydroxyacetone, depending upon pH, H2O2 concentration, temperature and the presence or absence of catalytic amounts of Fe2+. Glycolate was produced by dihydroxyacetone cleavage at rates up to 0.45 mmol h-1 in the absence, and up to 1.88 mmol h-1 in the presence of Fe2+ ions (pH 8). Besides glycolate, other sugars (ribose, glyceraldehyde, glucose), glucitol (sorbitol) and organic acids (formic and 2-oxogluconic acid) were produced in such H2O2-induced reactions with fructose or dihydroxyacetone. EPR measurements demonstrated the participation of the {radical dot}OH radical, especially at higher pH. Presence of metal ions at higher pH values, resulting in increased glycolate synthesis, was accompanied by enhanced hydroxyl radical generation. Observed changes in intensity of DEPMPO-OH signals recorded from dihydroxyacetone and fructose reactions demonstrate a strong correlation with changes in glycolate yield, suggesting that {radical dot}OH radical formation enhances glycolate synthesis. The results presented suggest that different mechanisms are responsible for the cleavage or other reactions (isomerisation, auto- or free-radical-mediated oxidation) of keto-monosaccharides depending of experimental conditions.

METHOD FOR SELECTIVE CARBOHYDRATE OXIDATION USING SUPPORTED GOLD CATALYSTS

The invention relates to a method for the selective oxidation of a carbohydrate in the presence of a gold catalyst comprising gold particles distributed in a nanodispersed manner on a metal oxide support, and to a method for the selective oxidation of an oligosaccharide in the presence of a gold catalyst comprising gold particles distributed in a nanodispersed manner on a carbon or metal oxide support. The invention also relates to aldonic acid oxidation products produced using said method.

Non-linear kinetics and mechanism of fructose and bromate reaction in acidic medium

Reaction between fructose [F] and bromate (BrO3-) is an important component of the F+Ce4++BrO3-+H2SO4 oscillatory reaction. Kinetics of this reaction has been experimentally investigated. A reaction mechanism has been proposed which is supported by computer simulation.

Regio- and stereo-selectivity in homogeneous catalytic hydrogenation of 2,5-diketo-D-threo-hexonic acid

2,5-Diketo-D-threo-hexonic acid (2,5-diketo-D-gluconic acid, 1), a crucial intermediate in the microbial production of L-threo-hex-2-enono-1,4-lactone (L-ascorbic acid, vitamin C), was isolated from the fermentation broth of bacterium Erwinia citreus ATCC 31623, and its regio- and stereo-selective hydrogenation, catalyzed by the water-soluble Ru(II) complex of tris(m-sulfophenyl)phosphine (TPPTS), was performed, The effect of hydrogen pressure, temperature, pH, and catalyst-to-substrate ratio on regio- and stereo-selectivity of the process was studied, at low pH, over 90% regioselectivity in favor of the reduction of the 5-keto group in 1 was achieved, affording L-xylo-2-hexulosonic acid (2-keto-L-gulonic acid, 2) as the main product. Maximal diastereoselectivity, i.e. ratio between 2 and 2-keto-n-gulonic acid (3) expressed as diastereomeric excess (d.e.%), amounted to ca. 50% and was not influenced by any of the above reaction parameters.

Oxidation of D-gluconic acid by chromium(IV) in perchloric acid

The oxidation of gluconic acid by chromium(VI) in perchloric acid has been found to follow the rate law: -dVI>/dt=(k'1 + k'2)+>2VI>, where k'1=(7.1+/-0.2)*10-4 M-2 s-1 and k'2=(9.4+/-0.2)*10-2 M-3 s-1.This rate law corresponds to the reaction leading to the formation of 2-ketogluconic acid by C-H cleavage when a 20-fold or higher excess of acid over chromium(VI) is employed.Buildup and decay of chromium(V) intermediates accompany the decay of chromium(VI).Chromium(V) rates of decay are similar or slower than those of chromium(VI), as observed by electron paramagnetic resonance (epr) and visible spectrophotometry.

THE SELECTIVE OXIDATION OF ALDOSES AND ALDONIC ACIDS TO 2-KETOALDONIC ACIDS WITH LEAD-MODIFIED PLATINUM-ON-CARBON CATALYSTS

Aldoses and aldonic acids have been oxidised with oxygen and air at 55 deg in water, using Pt/C catalysts.After oxidation of the reducing group, if available, the primary hydroxyl group is preferentially oxidised using an unmodified catalyst.Addition of a lead(II) salt changes the preference dramatically towards oxidation at the position α to the carboxyl group.Provided that oxygen transfer to the liquid phase is carefully controlled in order to prevent deactivation of the catalyst, 2-ketoaldonic acids can be prepared in high yields.

Process for the preparation of 2-keto-aldonic acids

Preparation of 2-keto-aldonic acids, e.g., 2-keto-gluconic acid, by oxidizing an aldose, e.g. glucose, or aldonic acid in aqueous solution with molecular oxygen. Use is made of a platinum catalyst together with a catalytic amount of lead and/or bismuth and/or a compound thereof. The pH of the solution is in the range of from 4 to 12 and preferably in the range of from 7 to 9. The reaction may be carried out at a temperature in the range of 0° to 200° C. and preferably in the range of from 25° to 80° C.