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2-Ketoglutaric acid

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2-Ketoglutaric acid Basic information
Product Name:2-Ketoglutaric acid
Synonyms:2-KETOGLUTARIC ACID;Glutaric acid, alpha keto;-Ketoglutaricacid;α-Ketoglutaricacid;PENTANEDIOIC ACID, 2-OXO-;2-Oxo-1,5-dipentanedioic acid;2-oxo-pentanedioicaci;2-Oxpentanedioicacid
CAS:328-50-7
MF:C5H6O5
MW:146.1
EINECS:206-330-3
Product Categories:Nutrition;food additives;pharm raw material;Pharmaceutical Intermediates;Aliphatics;Organic acids;Amino Acids;Food Additives;bc0001;328-50-7
Mol File:328-50-7.mol
2-Ketoglutaric acid Structure
2-Ketoglutaric acid Chemical Properties
Melting point 113-115 °C
Boiling point 185.67°C (rough estimate)
density 1.2821 (rough estimate)
vapor pressure 0.01Pa at 25℃
FEMA 3891 | 2-OXOPENTANEDIOIC ACID
refractive index 1.3920 (estimate)
storage temp. 2-8°C
solubility H2O: soluble0.1g/mL, clear, colorless
form Crystalline Powder
pka2.47(at 25℃)
color White to slightly yellow
PH3.09(1 mM solution);2.36(10 mM solution);1.77(100 mM solution)
OdorOdorless
Water Solubility Soluble in water, methanol and dimethyl sulfoxide.
Merck 14,5303
JECFA Number634
BRN 1705689
InChIKeyKPGXRSRHYNQIFN-UHFFFAOYSA-N
LogP-2.08 at 25℃
CAS DataBase Reference328-50-7(CAS DataBase Reference)
NIST Chemistry Reference2-Oxopentanedioic acid(328-50-7)
EPA Substance Registry SystemPentanedioic acid, 2-oxo- (328-50-7)
Safety Information
Hazard Codes Xi,T
Risk Statements 37/38-41-36/37/38-23/24/25
Safety Statements 26-39-45-36/37/39
WGK Germany 3
TSCA Yes
HS Code 29183000
MSDS Information
ProviderLanguage
alpha-Ketoglutaric acid English
SigmaAldrich English
ACROS English
ALFA English
2-Ketoglutaric acid Usage And Synthesis
Description2-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.
Chemical Properties2-Ketoglutaric acid is a white to yellowish crystalline powder. It is easily soluble in water, alcohol, and extremely insoluble in ether. It becomes light gray-yellow when stored for a long time, and is easy to deliquescence.
Uses2-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.
PreparationSynthesis of α-ketoglutaric acid: 225 g of triethyl nitrilotricarboxylate and 600 ml of concentrated hydrochloric acid were mixed and left to pass through. It was concentrated by distillation to 140°C, and the residue was crystallized by cooling to obtain 110-112 g of α-ketoglutaric acid with a yield of 92-93%.
DefinitionChEBI: 2-oxoglutaric acid is an oxo dicarboxylic acid that consists of glutaric acid bearing an oxo substituent at position 2. It is an intermediate metabolite in Krebs cycle. It has a role as a fundamental metabolite. It derives from a glutaric acid. It is a conjugate acid of a 2-oxoglutarate(1-).
Application2-Ketoglutaric acid is a derivative of glutaric acid. It plays an important role in the metabolism of microbial cells and It acts as precursor for the synthesis of amino acids and nucleotides. α-ketoglutaric acid along with L-arginine can undergo reduction with sodium cyanoborohydride to form the diastereomers, nopaline and isonopaline. α-ketoglutaric acid can be prepared in 1:1 and 2:1 L-arginine alpha-ketoglutarate for sports nutrition. mainly as an ingredient in sports nutrition drinks.
General Description2-Ketoglutaric acid is a 2-oxocarboxylic acid (2-OCA), one of the important intermediates in the Krebs cycle, after isocitrate and before succinyl CoA. It is an important nitrogen transporter and is transaminate along with glutamine to form glutamate. It can be used to differentiate microorganisms based on metabolic properties. It also possesses metabolic properties, decreasing the level of hydrogen peroxide in cell culture.
Flammability and ExplosibilityNot classified
Biotechnological Applicationsa-Ketoglutaric acid is an intermediate of the tricarboxylic acid cycle and the main compound of amino acid and protein metabolism. This organic acid could be used as building-block chemical for the chemical synthesis of heterocycles, dietary supplement, component of infusion solutions, and wound healing compounds (Otto et al. 2013).
Purification MethodsCrystallise the keto-acid repeatedly from Me2CO/*benzene, EtOAc or ethyl propionate. Dry it in vacuo.[Beilstein 3 IV 1813.]
Tag:2-Ketoglutaric acid(328-50-7) Related Product Information
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