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Merck
CN

K0629

Sodium 4-methyl-2-oxovalerate

leucine metabolite

Synonym(s):

α-Ketoisocaproic acid sodium salt, 4-Methyl-2-oxopentanoic acid sodium salt, 4-Methyl-2-oxovaleric acid sodium salt, Ketoleucine sodium salt

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About This Item

Linear Formula:
(CH3)2CHCH2COCOONa
CAS Number:
4502-00-5
Molecular Weight:
152.12
UNSPSC Code:
12352107
NACRES:
NA.25
PubChem Substance ID:
24896196
EC Number:
224-816-3
Beilstein/REAXYS Number:
4239297
MDL number:
MFCD00064193

Key Documents

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Product Name

Sodium 4-methyl-2-oxovalerate, leucine metabolite

InChI key

IXFAZKRLPPMQEO-UHFFFAOYSA-M

InChI

1S/C6H10O3.Na/c1-4(2)3-5(7)6(8)9;/h4H,3H2,1-2H3,(H,8,9);/q;+1/p-1

SMILES string

[Na+].CC(C)CC(=O)C([O-])=O

assay

>98% (TLC)

form

powder

technique(s)

HPLC: suitable

color

white to off-white

mp

275 °C (dec.) (lit.)

application(s)

cell analysis

storage temp.

2-8°C

Quality Level

100

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Application

Sodium 4-methyl-2-oxovalerate has been used for quantifying branched-chain keto acids from cell extracts by HPLC-fluorescence method.

Biochem/physiol Actions

α-Ketoisocaproic acid is a leucine metabolite that is known to induce insulin secretion from the βcells of pancreas. Enteral infusion of aα-Ketoisocaproate is found to ameliorate, endotoxemic condition. The resulting ketone bodies obtained from its conversion, might serve as an energy source. Accumulation of α-Ketoisocaproic acid is characterized in branched chain ketoaciduria, which is caused due to the lack of branched chain L-2-keto acid dehydrogenase activity. α-Ketoisocaproic acid causes dissociation in the oxidative phosphorylation reaction and acts as a metabolic inhibitor of α-ketoglutarate dehydrogenase. Thus, leads to a defect in the mitochondrial homeostasis, observed in branched chain ketoaciduria.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H319

Hazard Classifications

Eye Irrit. 2

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
MKCZ0523
MKCW8658
MKCV1405
MKCR0665
MKCR4766

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Enteral infusion of sodium 2-ketoisocaproate in endotoxic rats.
Hirokawa M and Walser M
Critical Care Medicine, 27(2), 373-379 (1999)
Effects of L-leucine and alpha-ketoisocaproic acid upon insulin secretion and metabolism of isolated pancreatic islets.
Panten U
Febs Letters, 20(2), 225-228 (1972)
Branched chain a- Keto acid metabolism
JOE A. BOWDEN
The Journal of Biological Chemistry, 243, 3526-3531 (1968)
Analysis of Branched-Chain Keto Acids in Cell Extracts by HPLC-Fluorescence Detention
Ayuna HATTORI
Chromatography, 38, 129-133 (2017)
Guoxing Fu et al.
Biochemistry, 50(29), 6292-6294 (2011-06-29)
D-Arginine dehydrogenase (DADH) catalyzes the flavin-dependent oxidative deamination of D-arginine and other D-amino acids to the corresponding imino acids. The 1.07 Å atomic-resolution structure of DADH crystallized with D-leucine unexpectedly revealed a covalent N(5) flavin adduct, instead of the expected
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