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

Definition

ChEBI: A ketoaldonic acid that is D-gluconic acid in which the hydroxy group at position 2 has been oxidised to a keto group.

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 
• 453-17-8 D-Glyceraldehyde 
• 1113-60-6 3-hydroxy-2-oxopropionic acid 

Downstream Products

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

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.

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.