2-Oxoglutaric acid

Base Information

• Chemical Name: 2-Oxoglutaric acid
• CAS No.: 328-50-7
• Deprecated CAS: 27175-99-1
• Molecular Formula: C5H6O5
• Molecular Weight: 146.1
• Hs Code.: 2922.49 DERIVATION
• European Community (EC) Number: 206-330-3,241-157-7,213-641-8
• NSC Number: 17391
• UNII: 8ID597Z82X
• DSSTox Substance ID: DTXSID5033179
• Nikkaji Number: J11.847H
• Wikipedia: %CE%91-Ketoglutaric_acid,Α-Ketoglutaric acid
• Wikidata: Q306140
• NCI Thesaurus Code: C83527
• Pharos Ligand ID: Q499MWKZN12P
• Metabolomics Workbench ID: 37135
• ChEMBL ID: CHEMBL1686
• Mol file: 328-50-7.mol

Synonyms:2 Ketoglutarate;2 Ketoglutaric Acid;2 Oxoglutarate;2 Oxoglutaric Acid;2-ketoglutarate;2-ketoglutaric acid;2-oxoglutarate;2-oxoglutaric acid;alpha Ketoglutarate;alpha Ketoglutaric Acid;alpha Ketoglutaric Acid, Diammonium Salt;alpha Ketoglutaric Acid, Dipotassium Salt;alpha Ketoglutaric Acid, Disodium Salt;alpha Ketoglutaric Acid, Monopotassium Salt;alpha Ketoglutaric Acid, Monosodium Salt;alpha Ketoglutaric Acid, Potassium Salt;alpha Ketoglutaric Acid, Sodium Salt;alpha Oxoglutarate;alpha-ketoglutarate;alpha-Ketoglutarate, Calcium;alpha-ketoglutaric acid;alpha-ketoglutaric acid, calcium salt (2:1);alpha-ketoglutaric acid, diammonium salt;alpha-ketoglutaric acid, dipotassium salt;alpha-ketoglutaric acid, disodium salt;alpha-ketoglutaric acid, monopotassium salt;alpha-ketoglutaric acid, monosodium salt;alpha-ketoglutaric acid, potassium salt;alpha-ketoglutaric acid, sodium salt;alpha-oxoglutarate;Calcium alpha Ketoglutarate;calcium alpha-ketoglutarate;calcium ketoglutarate;Ketoglutaric Acid;Ketoglutaric Acids;oxogluric acid;Oxoglutarates

Chemical Property of 2-Oxoglutaric acid

Chemical Property:

• Appearance/Colour: crystalline
• Vapor Pressure: 6.5E-05mmHg at 25°C
• Melting Point: 113-115 °C
• Refractive Index: 1.544
• Boiling Point: 345.6 °C at 760 mmHg
• PKA: 2.47(at 25℃)
• Flash Point: 177 °C
• PSA: 91.67000
• Density: 1.499 g/cm³
• LogP: -0.49510
• Storage Temp.: 2-8°C
• Solubility.: H2O: soluble0.1g/mL, clear, colorless
• Water Solubility.: Soluble in water, methanol and dimethyl sulfoxide.
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 146.02152329
• Heavy Atom Count: 10
• Complexity: 171

Purity/Quality:

98% ^*data from raw suppliers

2-Ketoglutaric Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi, T
• Hazard Codes: Xi,T
• Statements: 37/38-41-36/37/38-23/24/25
• Safety Statements: 26-39-45-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Uses -> Biochemical Research
• Canonical SMILES: C(CC(=O)O)C(=O)C(=O)O
• Recent ClinicalTrials: Alpha-Ketoglutarate and Abdominal Aortic Aneurysm Progression and Rupture
• Description: 2-Ketoglutaric acid also known as α-Ketoglutaric acid (AKG) is a chemical found in the body. It is a ketone derivative of the organic compound glutaric acid. It is important for the proper metabolism of all essential amino acids and the transfer of cellular energy in the citric acid or Krebs cycle. In combination with L-glutamate, AKG can reduce levels of ammonia formed in the brain, muscles, and kidneys, as well as help balance the body’s nitrogen chemistry and prevent nitrogen excess in body tissues and fluids.α-Ketoglutaric acid is used for kidney disease; intestinal and stomach disorders, including bacterial infections; liver problems; cataracts; and recurring yeast infections. It is also used for improving the way kidney patients receiving hemodialysis treatments process protein.
• Uses: 2-Ketoglutaric acid has a wide range of applications in the animal feed, food, pharmaceutical and fine chemistry industries. It is used as an intermediate in the kreb's cycle catalyzed by glutamate dehydrogenase enzyme on glutamate. It is also used in dietary supplements to improve protein synthesis.

Technology Process of 2-Oxoglutaric acid

There total 99 articles about 2-Oxoglutaric 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: 18.3%

Glutamic acid (617-65-2,21675-62-7,23009-64-5,25104-13-6,84960-48-5,25513-46-6) → α-ketoglutaric acid (328-50-7)

Guidance literature:

With zinc sulfide; sodium hydroxide; sodium sulfite; In water; at 30 ℃; for 4h; pH=9; Inert atmosphere; Irradiation;

DOI:10.1039/c2cc15665b

Reference yield:

L-glutamic acid (56-86-0,21675-62-7,23009-64-5,25104-13-6,84960-48-5,25513-46-6) + DL-homoalanin-4-yl(methyl)phosphinic acid (51276-47-2,53369-07-6) → α-ketoglutaric acid (328-50-7) + 4-(hydroxymethylphosphinyl)-2-oxobutanoic acid (79778-02-2) + L-phosphinothricin (35597-44-5,53369-07-6)

Guidance literature:

With magnesium(II) chloride hexahydrate; pyridoxal 5'-phosphate; E_.coli gabT transaminase E₂₁₁S mutant; thiamine diphosphate; sodium hydroxide; In aq. phosphate buffer; at 30 ℃; for 22.5h; pH=Ca.7.5; Enzymatic reaction;

Reference yield:

L-glutamine (56-85-9,26700-71-0) → α-ketoglutaric acid (328-50-7) + 2-keto-glutaramic acid (18465-19-5)

Guidance literature:

enzymatische Reaktion mit 2-Oxo-carbonsaeuren;

upstream raw materials:

methanol

1-bromo-cyclopropane-1,2-dicarboxylic acid

1-hydroxy-cyclopropane-1,2-dicarboxylic acid

L-glutamine

Downstream raw materials:

2-Oxo-glutarsaeure-isonicotinoylhydrazon

2-acetoacetic acid

L-glutamic acid

2-oxo-propionic acid

Refernces

• 1、 Zhang, Wen,Zhang, Manman,Gao, Chao,Zhang, Yipeng,Ge, Yongsheng,Guo, Shiting,Guo, Xiaoting,Zhou, Zikang,Liu, Qiuyuan,Zhang, Yingxin,Ma, Cuiqing,Tao, Fei,Xu, Ping. "Coupling between D-3-phosphoglycerate dehydrogenase and D-2-hydroxyglutarate dehydrogenase drives bacterial L-serine synthesis". . p. E7574 - E7582. Retrieved 2017.
• 2、 Ikawa,Snell. "-". . p. 653. Retrieved 1954.
• 3、 Lynen,Bayer,Holzer. "". . p. 66 - 73. Retrieved 1949.
• 4、 Yu, Xiaoyong,Wang, Lijing,Wang, Xin,Liu, Hongzhi,Wang, Ziyuan,Huang, Yixuan,Shan, Guoqiang,Wang, Weichao,Zhu, Lingyan. "Enhanced nonradical catalytic oxidation by encapsulating cobalt into nitrogen doped graphene: highlight on interfacial interactions". supporting information. p. 7198 - 7207. Retrieved 2021/03/29.
• 5、 Tian, Changqing,Wen, Bin,Bian, Mingjie,Jin, Mingming,Wang, Peng,Xu, Lei,Zhu, Guoping. "From a dimer to a monomer: Construction of a chimeric monomeric isocitrate dehydrogenase". . p. 2396 - 2407. Retrieved 2021/10/29.