1185549-38-5

Basic information

• Product Name: C₄⁽¹³⁾CH₁₀O₆
• Synonyms: C₄⁽¹³⁾CH₁₀O₆
• CAS NO: 1185549-38-5
• Molecular Weight: 167.12
• Mol File: 1185549-38-5.mol

Chemical Properties

• CAS DataBase Reference: C₄⁽¹³⁾CH₁₀O₆(CAS DataBase Reference)
• NIST Chemistry Reference: C₄⁽¹³⁾CH₁₀O₆(1185549-38-5)
• EPA Substance Registry System: C₄⁽¹³⁾CH₁₀O₆(1185549-38-5)

Safety Data

• Hazardous Substances Data: 1185549-38-5(Hazardous Substances Data)

Upstream product

• 70491-70-2 6-¹³C-D-glucose 

Relevant articles and documents

Successive C1-C2 bond cleavage: The mechanism of vanadium(v)-catalyzed aerobic oxidation of d-glucose to formic acid in aqueous solution

Vanadium(v)-catalyzed aerobic oxidation in aqueous solution shows high selectivity in the field of C-C bond cleavage of carbohydrates for chemicals with less carbon atoms. However, the pathway of C-C bond cleavage from carbohydrates and the conversion mechanism are unclear. In this work, we studied the pathway and the mechanism of d-glucose oxidation to formic acid (FA) in NaVO3-H2SO4 aqueous solution using isotope-labeled glucoses as substrates. d-Glucose is first transformed to FA and d-arabinose via C1-C2 bond cleavage. d-Arabinose undergoes similar C1-C2 bond cleavage to form FA and the corresponding d-erythrose, which can be further degraded by C1-C2 bond cleavage. Dimerization and aldol condensation between carbohydrates can also proceed to make the reaction a much more complicated mixture. However, the fundamental reaction, C1-C2 bond cleavage, can drive all the intermediates to form the common product FA. Based on the detected intermediates, isotope-labelling experiments, the kinetic isotope effect study and kinetic analysis, this mechanism is proposed. d-Glucose first reacts with a vanadium(v) species to form a five-membered-ring complex. Then, electron transfer occurs and the C1-C2 bond weakens, followed by C1-C2 bond cleavage (with no C-H bond cleavage), to generate the H3COO-vanadium(iv) complex and d-arabinose. FA is generated from H3COO that is oxidized by another vanadium(v) species. The reduced vanadium species is oxidized by O2 to regenerate to its oxidation state. This finding will provide a deeper insight into the process of C-C bond cleavage of carbohydrates for chemical synthesis and provide guidance for screening and synthesizing new highly-efficient catalyst systems for FA production.

Reaction pathways of glucose oxidation by ozone under acidic conditions

The ozonation of d-glucose-1-13C, 2-13C, and 6-13C was carried out at pH 2.5 in a semi-batch reactor at room temperature. The products present in the liquid phase were analyzed by GC-MS, HPAEC-PAD, and 13C NMR s