534-41-8

Basic information

• Product Name: cellobionic acid
• Synonyms: cellobionic acid;D-gluconic acid, 4-o-B-D-glucopyranosyl;Cellobionic acid ammonium salt
• CAS NO: 534-41-8
• Molecular Formula: C₁₂H₂₂O₁₂
• Molecular Weight: 358.3
• Mol File: 534-41-8.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 864.7°C at 760 mmHg
• Flash Point: 319.1°C
• Appearance: /
• Density: 1.79g/cm³
• Vapor Pressure: 7.15E-35mmHg at 25°C
• Refractive Index: 1.648
• Storage Temp.: Hygroscopic, Refrigerator, Under Inert Atmosphere
• Solubility: DMSO, (Slightly) Water (Slightly)
• PKA: 3.28±0.35(Predicted)
• CAS DataBase Reference: cellobionic acid(CAS DataBase Reference)
• NIST Chemistry Reference: cellobionic acid(534-41-8)
• EPA Substance Registry System: cellobionic acid(534-41-8)

Safety Data

• Hazardous Substances Data: 534-41-8(Hazardous Substances Data)

Usage

Description

Cellobionic acid, derived from the ozonization of cellobiose, is a compound that possesses unique properties due to its lactonized carboxyl group. This group inhibits enzymatic hydrolysis, making cellobionic acid a distinct substance in the realm of biochemistry.

Uses

Used in Enzyme Research:
Cellobionic acid is used as a research compound for studying the effects of lactonized carboxyl groups on enzymatic hydrolysis. The inhibition of β-Glucosidase by cellobionic acid can provide insights into enzyme specificity and the development of new biocatalysts.
Used in Biochemical Applications:
Cellobionic acid is used as a substrate modifier in biochemical applications to explore the impact of its lactonized carboxyl group on various enzymatic reactions. This can lead to a better understanding of enzyme-substrate interactions and the potential for designing more efficient biocatalytic processes.
Used in Pharmaceutical Development:
Cellobionic acid, with its inhibitory effect on enzymatic hydrolysis, can be utilized in the development of pharmaceuticals targeting specific enzymes. By understanding the interaction between cellobionic acid and enzymes like gluconolactonase, researchers can potentially design drugs that modulate enzyme activity for therapeutic purposes.

InChI:InChI=1/C12H22O12/c13-1-3(15)10(7(18)8(19)11(21)22)24-12-9(20)6(17)5(16)4(2-14)23-12/h3-10,12-20H,1-2H2,(H,21,22)/t3-,4-,5-,6+,7-,8-,9-,10-,12+/m1/s1

Upstream product

• 5965-66-2 LACTOSE 
• 5965-65-1 lactobionolactone 
• 63-42-3 D-(+)-lactose 
• 6057-48-3 3-O-β-D-galactopyranosyl-D-arabinose 
• 13360-52-6 Cellobiose 
• 536-11-8 gentibiose 
• 528-50-7 cellobiose 

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 
• 173543-54-9 lactoseamidemethylbenzoic acid 
• 3847-29-8 erythromycin lactobionate 
• 148526-30-1 C₂₂H₃₄N₂O₁₃ 
• 918802-82-1 N-galactosylamino-N'-phenylpiperazine 
• 5965-65-1 lactobionolactone 

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.

Gold as active phase of BN-supported catalysts for lactose oxidation

Au/h-BN catalysts have been prepared by wet impregnation in order to combine the high activity of gold with the promising h-BN support to optimize the catalytic performances in lactose oxidation. After 1 h reaction, the catalysts were more active than all the Pd/h-BN catalysts described in previous works: 100% yield was reached after 2 h for a Au/h-BN catalyst prepared in water and containing only 1 wt.% of gold. The influence of α-Al2O3, γ-Al2O3 and Cblack as supports for Au was compared to h-BN and Au/α-Al2O3 was the most active. All of them exhibited 100% selectivity toward lactobionic acid. After a second run, Au/γ-Al2O3 presented a loss of selectivity and all were less active than during their first run. Au/h-BN and Au/α-Al2O3 have been regenerated and a thermal treatment permits to keep the catalysts active with 100% selectivity. Au/h-BN was the most active after regeneration thanks to the more facile poison removal from its surface and the high stability of boron nitride.

Selective production of lactobionic acid by aerobic oxidation of lactose over gold crystallites supported on mesoporous silica

Partial oxidation of lactose over Au-based catalyst system using nanostructured silica materials with improved activity, selectivity and stability was investigated as a novel chemo-catalytic approach for selective synthesis of lactobionic acid (LBA) for therapeutic, pharmaceutical and food grad applications. Highly active gold crystallites dispersed on mesoporous silica (SiO2-meso) using bis-[3-(triethoxysilyl) propyl] tetrasulfide (BTSPT), a silane coupling agent to immobilize gold, were successfully formulated, and their catalytic activity was evaluated in an agitated semi-batch reactor. The catalysts were characterized by N2 physisorption, XRD, XPS and TEM. The influence of the reaction conditions, i.e., temperature, pH value, metal loading and catalyst/lactose ratio on lactose conversion were investigated. After 100 min of reaction, the catalyst containing 0.7% Au showed the highest catalytic activity (100% lactose conversion) and a 100% selectivity towards LBA, when it was used at a catalyst/lactose ratio of 0.2 under alkaline (pH 9.0) and mild reaction temperature (65 °C).