5155-45-3

Basic information

• Product Name: methyl α-D-glucopyranosiduronic acid
• Synonyms: methyl α-D-glucopyranosiduronic acid
• CAS NO: 5155-45-3
• Molecular Weight: 208.168
• Mol File: 5155-45-3.mol
• Article Data: 16

Chemical Properties

• CAS DataBase Reference: methyl α-D-glucopyranosiduronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: methyl α-D-glucopyranosiduronic acid(5155-45-3)
• EPA Substance Registry System: methyl α-D-glucopyranosiduronic acid(5155-45-3)

Safety Data

• Hazardous Substances Data: 5155-45-3(Hazardous Substances Data)

Upstream product

• 100201-60-3 sophoraflavoside I 
• 23598-27-8 methyl α-D-gluco-hexodialdo-1,5-pyranoside 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 67-56-1 methanol 
• 82793-05-3 3-O-[α-L-rhamnopyranosyl(1->2)-β-D-glucopyranosyl(1->2)-β-D-glucuronopyranosyl]olean-12-en-3β,22β,24-triol 
• 55319-36-3 astragaloside VIII 
• 82793-03-1 3-O-[β-D-glucopyranosyl(1->2)-β-D-glucuronopyranosyl]olean-12-en-3β,22β,24-triol 
• 82793-02-0 azukisaponin I 
• 143519-29-3 Cloversaponin IV methyl ester 
• 78693-93-3 soyasaponin A₂ 
• 82801-38-5 azukisaponin III 
• 78693-94-4 soyasaponin A₁ 
• 709-50-2 methyl beta-D-glucopyranoside 
• 118325-22-7 licorice-saponin A₃ 

Downstream Products

• 18486-51-6 1-O-methyl-α-D-glucopyranuronic acid methyl ester 
• 87-99-0 XYLITOL 
• 18486-38-9 methyl β-D-glucuronopyranoside methyl ester 
• 6556-12-3 D-glucuronic acid 

Relevant articles and documents

Bromide-free TEMPO-mediated oxidation of primary alcohol groups in starch and methyl α-D-glucopyranoside

TEMPO (2,2,6,6-tetramethylpiperidine-1-oxyl)-mediated oxidation of potato starch and methyl α-D-glucopyranoside (MGP) was performed in the absence of sodium bromide (NaBr) as co-catalyst, solely using sodium hypochlorite (NaOCl) as the primary oxidant. The low reaction rate associated with a bromide-free process was increased by performing the oxidation at increased temperatures. The reaction proceeded stoichiometrically and with high selectivity and with only minor depolymerisation, provided that temperature and pH were kept ≤20°C and a corresponding oxidation catalysed by NaBr at 2°C. Consequently, this is a simple approach to raise the TEMPO/NaOCl reaction rate under bromide-free conditions while still maintaining good product properties. At higher oxidation temperatures (≥25°C) and under more alkaline conditions (pH ≥ 9.0) degradation of the starch skeleton occurred. Simultaneously, side-reactions of the nitrosonium ion lowered the yield of the oxidation. Despite the absence of the NaBr catalyst, the reaction rate-controlling step was found to be the oxidation of the primary hydroxyl groups with the nitrosonium ion. The reaction was first- order in MGP and in TEMPO. (C) 2000 Elsevier Science Ltd.

Toward glucuronic acid through oxidation of methyl-glucoside using PdAu catalysts

The production of glucuronic acid via enzyme catalysis from biomass is slow. Here we studied the oxidation of methoxy-protected glucose (MG) using Pd-on-Au nanoparticle model catalysts to generate methoxy-protected glucuronic acid (MGA), a precursor to glucuronic acid. Pd-on-Au showed volcano-shape activity dependence on calculated Pd surface coverage (sc). The 80 sc% Pd-on-Au catalyst composition showed maximum initial turnover frequency (413 mol-MG mol-surface-atom?1 h?1) that was 5× higher than that of Au/C, while Pd/C was inactive. This Pd-on-Au composition gave the highest MGA yield (46%), supporting a bimetallic approach to glucuronic acid production.

Process for oxidizing primary alcohols

Primary hydroxyl groups in a substrate having both primary and secondary hydroxyl groups can be selectively oxidized to carbaldehyde and/or carboxyl groups by contacting the substrate with a cyclic nitroxyl compound in the presence of a peroxosulfate as a co-oxidant and by carrying out the reaction at a temperature below 30° C. and at a pH below 9. The process is halogen-free and metal-free and is especially suitable for oxidizing polysaccharides.