5-keto-D-gluconic acid

Base Information

• Chemical Name: 5-keto-D-gluconic acid
• CAS No.: 5287-64-9
• Deprecated CAS: 138127-14-7
• Molecular Formula: C6H10O7
• Molecular Weight: 194.141
• European Community (EC) Number: 923-251-6
• UNII: 5168T78Z4V
• DSSTox Substance ID: DTXSID6046927
• Nikkaji Number: J92.813E
• Wikidata: Q27102394
• Metabolomics Workbench ID: 50909
• ChEMBL ID: CHEMBL3307203
• Mol file: 5287-64-9.mol

Synonyms:5-ketogluconic acid;5-ketogluconic acid, hemicalcium salt;5-ketogluconic acid, potassium salt

Chemical Property of 5-keto-D-gluconic acid

Chemical Property:

• PSA: 135.29000
• LogP: -3.28490
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Methanol (Slightly, Sonicated), Water (Sparingly, Sonicated)
• XLogP3: -3
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 194.04265265
• Heavy Atom Count: 13
• Complexity: 201

Purity/Quality:

99% ^*data from raw suppliers

5-Keto-D-gluconic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(C(=O)C(C(C(C(=O)O)O)O)O)O
• Isomeric SMILES: C(C(=O)[C@H]([C@@H]([C@H](C(=O)O)O)O)O)O
• Uses: 5-Keto-D-gluconic Acid was identified in anaerobic actinobacterium (strain CBA3103T), which was isolated from the sediment of the Geum River in South Korea.

Technology Process of 5-keto-D-gluconic acid

There total 5 articles about 5-keto-D-gluconic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

alpha-D-glucopyranose (492-62-6) → D-glucuronic acid (6556-12-3,489-91-8,528-16-5,552-12-5,577-46-8,643-33-4,2240-07-5,6294-16-2,10133-02-5,18402-78-3,18968-14-4,21179-08-8,23018-83-9,33599-45-0,33599-46-1,46171-67-9,46171-69-1,46172-26-3,70021-34-0,71031-08-8,104195-06-4,106499-29-0,124817-72-7) + D-fructose (470-23-5) + gluconic acid (526-95-4) + fructonic acid (669-90-9,16533-48-5,29123-55-5,20248-27-5) + 5-keto-D-gluconic acid (5287-64-9) + D-glucaric acid (87-73-0,7231-46-1)

Guidance literature:

With oxygen; Pt(5%)Bi(5%)/C; at 40 ℃; under 750.075 Torr; pH=11; Product distribution / selectivity;

Reference yield:

D-glucose (50-99-7) → gluconic acid (526-95-4) + 5-keto-D-gluconic acid (5287-64-9)

Guidance literature:

Bei der Oxydation an einer Platin-Anode;

DOI:10.1021/ja01307a507

Reference yield:

2,5-diketo-D-gluconic acid (2595-33-7) → fructonic acid (669-90-9,16533-48-5,29123-55-5,20248-27-5) + 2-keto-L-gulonic acid (526-98-7,16533-48-5,29123-55-5,20248-27-5) + D-lyxo-hex-5-ulosonic acid (13425-76-8) + 5-keto-D-gluconic acid (5287-64-9)

Guidance literature:

With Ru-TPPTS; sulfuric acid; hydrogen; sodium iodide; In water; at 27 ℃; for 8h; under 7500.6 Torr; Product distribution; other pH, temperature, reaction time, hydrogen pressure, catalyst amount;

DOI:10.1016/S0008-6215(97)00121-3

upstream raw materials:

2,5-diketo-D-gluconic acid

D-glucose

alpha-D-glucopyranose

L-Rhamnose

Downstream raw materials:

furan-2,5-dicarboxylic acid

5-Formyl-2-furancarboxylic acid

DL-tartaric acid

xylaric acid

Refernces

• 1、 Hamersak, Zdenko,Pavlovic, Nediljko,Delic, Vladimir,Sunjic, Vitomir. "Regio- and stereo-selectivity in homogeneous catalytic hydrogenation of 2,5-diketo-D-threo-hexonic acid". . p. 245 - 249. Retrieved 2007/10/03.