534-42-9

Basic information

• Product Name: 4-O-(α-D-Glucopyranosyl)-D-gluco-hexonic acid
• Synonyms: 4-O-(α-D-Glucopyranosyl)-D-gluco-hexonic acid;4-O-α-D-Glucopyranosyl-D-gluconic acid;Maltobionic acid;D-Gluconic acid, 4-o-alpha-D-glucopyranosyl-;4-O-(alpha-D-Glucopyranosyl)-D-gluco-hexonic acid;4-O-alpha-D-Glucopyranosyl-D-gluconic acid
• CAS NO: 534-42-9
• Molecular Formula: C₁₂H₂₂O₁₂
• Molecular Weight: 358.29588
• Mol File: 534-42-9.mol
• Article Data: 10

Chemical Properties

• Melting Point: 155-157 °C (decomp)
• Boiling Point: 864.7±65.0 °C(Predicted)
• Appearance: /
• Density: 1.79±0.1 g/cm3(Predicted)
• PKA: 3.28±0.35(Predicted)
• CAS DataBase Reference: 4-O-(α-D-Glucopyranosyl)-D-gluco-hexonic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-O-(α-D-Glucopyranosyl)-D-gluco-hexonic acid(534-42-9)
• EPA Substance Registry System: 4-O-(α-D-Glucopyranosyl)-D-gluco-hexonic acid(534-42-9)

Safety Data

• Hazardous Substances Data: 534-42-9(Hazardous Substances Data)

Usage

General Description

4-O-(α-D-Glucopyranosyl)-D-gluco-hexonic acid is a chemical compound that consists of a glucose molecule attached to a gluco-hexonic acid moiety at the 4-O position in a glycosidic bond. It is often referred to as glucosylgluconic acid and is used in certain industrial and food applications as a chelating agent, stabilizer, and acidulant. 4-O-(α-D-Glucopyranosyl)-D-gluco-hexonic acid has properties that make it useful for various purposes, including as a complexing agent in metal ion binding, a supplement in animal feed, and a component in pharmaceutical formulations. Additionally, glucosylgluconic acid has been studied for its potential health benefits, such as its antioxidant and antidiabetic effects, suggesting potential applications in the fields of nutrition and medicine.

Upstream product

• 69-79-4 D-maltose 
• 536-11-8 D-melibiose 
• 23103-02-8 O³-α-D-Glucopyranosyl-D-arabinose 
• 5965-65-1 lactobionolactone 
• 63-42-3 D-(+)-lactose 
• 6057-48-3 3-O-β-D-galactopyranosyl-D-arabinose 
• 5965-66-2 LACTOSE 

Downstream Products

• 888616-12-4 N-[1-(dodecylcarbamoyl-2-(trityl)imidazolyl)ethyl]-22-lactobionamido-12,12,13,13,14,14,15,15,16,16,17,17,18,18,19,19-hexadecafluorodocosanamide 
• 3847-29-8 erythromycin lactobionate 
• 148526-30-1 C₂₂H₃₄N₂O₁₃ 
• 918802-82-1 N-galactosylamino-N'-phenylpiperazine 
• 5965-65-1 lactobionolactone 
• 173543-54-9 lactoseamidemethylbenzoic acid 

Relevant articles and documents

Aqueous oxidation of sugars into sugar acids using hydrotalcite-supported gold nanoparticle catalyst under atmospheric molecular oxygen

Hydrotalcite-supported gold nanoparticles show good activity as a heterogeneous catalyst for the oxidation of monosaccharides (xylose, ribose, galactose and mannose) and disaccharides (lactose and cellobiose) into the corresponding sugar acids under external base-free conditions in water solvent using atmospheric pressure of molecular oxygen. The produced sugar acids were thoroughly identified by 1H-, 13C-, and HMQC-NMR and ESI-FT-ICR MS spectroscopic techniques.

Boron nitride as an alternative support of Pd catalysts for the selective oxidation of lactose

The potential of boron nitride as innovative support for the selective oxidation of carbohydrates has been evaluated. Pd/h-BN catalysts as well as Pd/α-Al2O3 have been synthesized by two different methods for comparison: dry impregnation and deposition-precipitation. It is shown that BN is a suitable alternative to alumina and carbon for sugar oxidation in liquid phase. Very active and selective Pd/h-BN catalysts were obtained by the two synthetic methods under consideration.

Production of lactose-free galacto-oligosaccharide mixtures: comparison of two cellobiose dehydrogenases for the selective oxidation of lactose to lactobionic acid

Galacto-oligosaccharides, complex mixtures of various sugars, are produced by transgalactosylation from lactose using β-galactosidase and are of great interest for food and feed applications because of their prebiotic properties. Most galacto-oligosaccharide preparations currently available in the market contain a significant amount of monosaccharides and lactose. The mixture of galacto-oligosaccharides (GalOS) in this study produced from lactose using recombinant β-galactosidase from Lactobacillus reuteri contains 48% monosaccharides, 26.5% lactose and 25.5% GalOS. To remove efficiently both monosaccharides and lactose from this GalOS mixture containing significant amounts of prebiotic non-lactose disaccharides, a biocatalytic approach coupled with subsequent chromatographic steps was used. Lactose was first oxidised to lactobionic acid using fungal cellobiose dehydrogenases, and then lactobionic acid and monosaccharides were removed by ion-exchange and size-exclusion chromatography. Two different cellobiose dehydrogenases (CDH), originating from Sclerotium rolfsii and Myriococcum thermophilum, were compared with respect to their applicability for this process. CDH from S. rolfsii showed higher specificity for the substrate lactose, and only few other components of the GalOS mixture were oxidised during prolonged incubation. Since these sugars were only converted once lactose oxidation was almost complete, careful control of the CDH-catalysed reaction will significantly reduce the undesired oxidation, and hence subsequent removal, of any GalOS components. Removal of ions and monosaccharides by the chromatographic steps gave an essentially pure GalOS product, containing less than 0.3% lactose and monosaccharides, in a yield of 60.3%.