498-43-1

Basic information

• Product Name: 3-deoxy-D-gluconic acid
• Synonyms: 3-deoxy-D-gluconic acid;3-Deoxy-D-ribo-hexonic acid;2,4,5,6-tetrahydroxyhexanoic acid
• CAS NO: 498-43-1
• Molecular Formula: C₆H₁₂O₆
• Molecular Weight: 180.15588
• EINECS: 207-862-9
• Mol File: 498-43-1.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 583.8°Cat760mmHg
• Flash Point: 320.9°C
• Appearance: /
• Density: 1.589g/cm³
• Refractive Index: 1.574
• CAS DataBase Reference: 3-deoxy-D-gluconic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-deoxy-D-gluconic acid(498-43-1)
• EPA Substance Registry System: 3-deoxy-D-gluconic acid(498-43-1)

Safety Data

• Hazardous Substances Data: 498-43-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C6H12O6/c7-2-5(10)3(8)1-4(9)6(11)12/h3-5,7-10H,1-2H2,(H,11,12)/t3-,4-,5-/m1/s1

Upstream product

• 50-99-7 D-glucose 
• 146-72-5 3-O-methyl-D-glucose 
• 124-41-4 sodium methylate 
• 7732-18-5 water 
• 120581-02-4 O³-phosphono-D-glucose; barium salt 
• 102731-63-5 O-(3-deoxy-L-erythro-hexulofuranosylic acid)-(2-3)-O-ribosyl-(1-1)-ethane-1,2-diol 
• 5349-40-6 α-D-glucopyranosyl-(1→3)-α-D-fructopyranose 
• 2495-70-7 nigerose 
• 141-52-6 sodium ethanolate 
• 57-48-7 D-Fructose 
• 7625-23-2 3,6-anhydro-D-glucose 

Downstream Products

• 499-87-6 3-deoxy-D-ribo-hexono-1,4-lactone 

Relevant articles and documents

Alkoxycarbonyl elimination of 3-O-substituted glucose and fructose by heat treatment under neutral pH

3-O-Substituted reducing aldoses are commonly unstable under heat treatment at neutral and alkaline pH. In this study, to evaluate the decomposition products, nigerose (3-O-α-D-glucopyranosyl-D-glucose) and 3-O-methyl glucose were heated at 90 °C in 100 mM sodium phosphate buffer (pH 7.5). Decomposition via β-elimination was observed that formed a mixture of 3-deoxy-arabino-hexonic acid and 3-deoxy-ribo-hexonic acid; upon further acid treatment, it was converted to their γ-lactones. Similarly, turanose (3-O-α-D-glucopyranosyl-D-fructose), a ketose isomer of nigerose, decomposed more rapidly than nigerose under the same conditions, forming the same products. These findings indicate that 3-O-substituted reducing glucose and fructose decompose via the same 1,2-enediol intermediate. The alkoxycarbonyl elimination of 3-O-substituted reducing glucose and fructose occurs readily if an O-glycosidic bond is located on the carbon adjacent to the 1,2-enediol intermediate. Following these experiments, we proposed a kinetic model for the3- decomposition of nigerose and turanose by heat treatment under neutral pH conditions. The proposed model showed a good fit with the experimental data collected in this study. The rate constant of the decomposition for nigerose was (1.2 ± 0.1) × 10?4 s?1, whereas that for turanose [(2.6 ± 0.2) × 10?4 s?1] was about 2.2 times higher.

Structure of the K95 antigen from Escherichia coli O75:K95:H5, a capsular polysaccharide containing furanosidic KDO-residues.

The structure of the K95 antigenic capsular polysaccharide (K95 antigen) of Escherichia coli O75:K95:H5 was elucidated by determination of the composition, 1H- and 13C-n.m.r. spectroscopy, periodate oxidation, and methylation analysis. The K95 polysaccharide, which contains furanosidic 3-deoxy-D-manno-2-octulosonic acid (KDOf) residues, consists of----3)-beta-D-Rib-(1----8)-KDOf-(2----repeating units, has a molecular weight of approximately 25,000 (approximately 65 repeating units), and is randomly O-acetylated (1 acetyl group per repeating unit at unknown positions).