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2-Ketoglutaric acid

CAS No.
328-50-7
Chemical Name:
2-Ketoglutaric acid
Synonyms
Oxoglutaric acid;α-Ketoglutaric acid;ALPHA-KETOGLUTARIC ACID;2-OXOGLUTARIC ACID;2-OXOPENTANEDIOIC ACID;A-KETOGLUTARIC ACID;α-KG;2-ketoglutarate;KETO-GLU;Oxoglurate
CBNumber:
CB1371815
Molecular Formula:
C5H6O5
Molecular Weight:
146.1
MDL Number:
MFCD00004165
MOL File:
328-50-7.mol
MSDS File:
SDS
Last updated:2024-04-25 09:45:49

2-Ketoglutaric acid 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
pka 2.47(at 25℃)
color White to slightly yellow
PH 3.09(1 mM solution);2.36(10 mM solution);1.77(100 mM solution)
Odor Odorless
Water Solubility Soluble in water, methanol and dimethyl sulfoxide.
Merck 14,5303
JECFA Number 634
BRN 1705689
InChIKey KPGXRSRHYNQIFN-UHFFFAOYSA-N
LogP -2.08 at 25℃
Substances Added to Food (formerly EAFUS) 2-OXOPENTANEDIOIC ACID
CAS DataBase Reference 328-50-7(CAS DataBase Reference)
FDA UNII 8ID597Z82X
NIST Chemistry Reference 2-Oxopentanedioic acid(328-50-7)
EPA Substance Registry System Pentanedioic acid, 2-oxo- (328-50-7)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS05
Signal word  Danger
Hazard statements  H318
Precautionary statements  P280-P305+P351+P338+P310
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
NFPA 704
0
2 0

2-Ketoglutaric acid price More Price(45)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 75890 α-Ketoglutaric acid ≥99.0% (T) 328-50-7 25g $43.2 2024-03-01 Buy
Sigma-Aldrich 75890 α-Ketoglutaric acid ≥99.0% (T) 328-50-7 100g $103 2024-03-01 Buy
Sigma-Aldrich 61234 α-Ketoglutaric acid analytical standard 328-50-7 10MG $80.9 2022-05-15 Buy
Sigma-Aldrich 61234 α-Ketoglutaric acid analytical standard 328-50-7 50MG $198 2022-05-15 Buy
TCI Chemical K0005 2-Oxoglutaric Acid >99.0%(T) 328-50-7 25g $53 2024-03-01 Buy
Product number Packaging Price Buy
75890 25g $43.2 Buy
75890 100g $103 Buy
61234 10MG $80.9 Buy
61234 50MG $198 Buy
K0005 25g $53 Buy

2-Ketoglutaric acid Chemical Properties,Uses,Production

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.

Chemical Properties

2-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.

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.

Preparation

Synthesis 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%.

Definition

ChEBI: 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-).

Application

2-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 Description

2-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 Explosibility

Not classified

Biotechnological Applications

a-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 Methods

Crystallise the keto-acid repeatedly from Me2CO/*benzene, EtOAc or ethyl propionate. Dry it in vacuo.[Beilstein 3 IV 1813.]

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328-50-7
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2-Ketoglutaric acid pictures 2024-04-22 2-Ketoglutaric acid
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US $0.00 / kg 1kg 99.8% 1000 kg BINBO BIOLOGICAL CO.,LTD
2-ketoglutaric acid pictures 2024-04-07 2-ketoglutaric acid
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US $0.00-0.00 / Kg 1Kg 99.9% 200 tons airuikechemical co., ltd.
Alpha Ketoglutaric Acid pictures 2023-11-30 Alpha Ketoglutaric Acid
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US $10.00 / Kg/Bag 1KG 99% HPLC,USP Standard 1000KGs ZhenYiBio Technology Inc
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 GAMMA-KETOGLUTARIC ACID FEMA 3891 A-KetoglutaricAcidPuriss KetoglutaricAcid,FreeAcid A-KETOGLUTARIC ACID FREE ACID CELL*CULTU RE TESTED A-KETOGLUTARIC ACID FREE ACID 2-KETOGLUTARIC ACID BIOSYNTH 2-KETOGLUTARIC ACID 99+% 2-KETOGLUTARIC ACID, DISODIUM SALT, DIHYDRATE BIOTECH GRADE 99.5% 2-OXOPENTANDIOICACID 2-KETOGLUTARIC ACID 98.5% 2-Ketoglutaric acid,98% 2-Oxoglutaric acid, 2-Oxopentanedioic acid KETOGLUTARIC ACID, ALPHA (SH) α-Ketoglutaric acid ,99% α-Ketoglutaric acid,2-Oxoglutaric acid, 2-Oxopentanedioic acid 2-Oxoglutaric acid, extra pure 2-Ketoglutaric acid, 98% 100GR 2-Ketoglutaric acid, 98% 25GR α-Ketoglutaric acid(AKG) 2-Ketoglutaric acid SynonyMs 2-Oxoglutaric acid alpha-Ketoglutaric acid >=99.0% (T) α-Ketog Alpha - ketone Α-Oxoglutaric Or Alpha-Ketoglutaric Acid α-Ketoglutaric acid, 99%, reagent grade 2-OxoglutaricAcid> PECTINASN,N-DIMETHYL-P-TOLUIDINEE α-KetogL 2-oxoglutaricaci 2-Ketoglutaric acidr α-Ketoglutaric acid, 99%+ a-Ketoglutaric acid puriss,99% 25GM a-Ketoglutaric Acid (High Purity) extrapure AR, 99.5% α-KETOGLUTARIC ACID Extra Pure 3'-cGAMP 2-OXOGLUTARIC ACID 2-OXOPENTANEDIOIC ACID A-KETOGLUTARIC ACID Glutaric acid, 2-oxo- 2-Oxo-1,5-pentanedioic acid ALPHA-KETOGLUTARIC ACID KETO-GLU Oxoglutaric acid β-ketoadipic acid α-KG Oxoglurate 2-ketoglutarate α-Ketoglutaric acid AKG (2-Ketoglutaric acid)