4502-00-5

Basic information

• Product Name: Sodium ketoisocaproate
• Synonyms: Sodium ketoisocaproate;SODIUM 4-METHYL-2-OXOVALERATE;SODIUM ALPHA-KETOISOCAPRATE;2-KETOISOCAPROIC ACID SODIUM SALT;2-KETOISOHEXANOIC ACID SODIUM SALT;A-KETOISOCAPROIC ACID, SODIUM SALT;ALPHA-KETOISOCAPROIC ACID SODIUM SALT;4-Methyl-2-oxopentanoic acid monosodium salt
• CAS NO: 4502-00-5
• Molecular Formula: C₆H₉O₃*Na
• Molecular Weight: 152.12
• EINECS: 224-816-3
• Product Categories: pharmacetical
• Mol File: 4502-00-5.mol
• Article Data: 5

Chemical Properties

• Melting Point: 275 °C (dec.)(lit.)
• Boiling Point: 190.5 °C at 760 mmHg
• Flash Point: 83.3 °C
• Appearance: COA
• Vapor Pressure: 0.239mmHg at 25°C
• Storage Temp.: 2-8°C
• Solubility: Water (Slightly)
• Stability: Hygroscopic
• BRN: 4239297
• CAS DataBase Reference: Sodium ketoisocaproate(CAS DataBase Reference)
• NIST Chemistry Reference: Sodium ketoisocaproate(4502-00-5)
• EPA Substance Registry System: Sodium ketoisocaproate(4502-00-5)

Safety Data

• Safety Statements: 24/25-22
• WGK Germany: 3
• Hazardous Substances Data: 4502-00-5(Hazardous Substances Data)

Usage

Occurrence

Reported found in banana, asparagus, cheese, white wine, cocoa, blue cheese and provolone cheese.

Uses

Different sources of media describe the Uses of 4502-00-5 differently. You can refer to the following data:
1. Sodium 4-methyl-2-oxovalerate has been used for quantifying branched-chain keto acids from cell extracts by HPLC-fluorescence method.
2. 4-Methyl-2-oxovaleric Acid is an α-ketomonocarboxylic acid that triggers insulin release by acting upon receptor sites which differ from those occupied by amino acids. 4-Methyl-2-oxovaleric Acid is an intermediate in the metabolism of Leucine.

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.

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

Upstream product

• 55666-11-0 C₇H₁₀N₂O₂ 
• 26073-09-6 ethyl 4-methyl-2-oxopentanoate 
• 344886-78-8 5'-isobutylidenecyclohexanespiro-2'-(1',3'-dioxolan)-4'-one 

Downstream Products

• 164400-78-6 [Ru(H)(CO)(P(C₆H₅)3)2(OOCC(CH₂CH(CH₃)2)N(CH₂C₆H₅))] 
• 96136-13-9 4-methyl-2-oxo-pentanoic phenylmethyl ester acid 
• 429661-38-1 C₂₀H₂₅Cl₂N₃O₄ 
• 429661-37-0 C₂₀H₂₅Cl₂N₃O₄ 
• 128972-02-1 4-methyl-2-oxo-N-(2-oxo-2-phenylethyl)pentanamide 
• 26073-09-6 ethyl 4-methyl-2-oxopentanoate 
• 816-66-0 4-methyl-2-oxopentanoic acid 
• 215311-47-0 4-methyl-2-oxo pentanoic 1-(S)-ethoxycarbonyl phenyl methyl ester acid 
• 128972-34-9 (1S,2S)-2-<(8-isobutyl-6-phenyl-1,2,4-triazolo<4,3-a>pyrazin-3-yl)acetamido>-1,3-dicyclohexyl-1-hydroxypropane 
• 128901-32-6 (8-isobutyl-6-phenyl-1,2,4-triazolo<4,3-a>pyrazin-3-yl)acetic acid 
• 128972-00-9 3-(2-methylpropyl)-5-phenyl-2(1H)-pyrazinone 
• 128972-39-4 (3S,4S)-5-Cyclohexyl-3-hydroxy-4-[2-(8-isobutyl-6-phenyl-[1,2,4]triazolo[4,3-a]pyrazin-3-yl)-acetylamino]-pentanoic acid {(S)-3-methyl-1-[(pyridin-2-ylmethyl)-carbamoyl]-butyl}-amide 
• 128972-36-1 (1S,2S)-2-<(2RS)-2-(8-isobutyl-6-phenyl-1,2,4-triazolo<4,3-a>pyrazin-3-yl)-3-imidazol-4-yl propionamido>-1,3-dicyclohexyl-1-hydroxypropane 

Relevant articles and documents

Independent valine and leucine isotope labeling in Escherichia coli protein overexpression systems

The addition of labeled α-ketoisovalerate to the growth medium of a protein-expressing host organism has evolved into a versatile tool to achieve concomitant incorporation of specific isotopes into valine- and leucine-residues. The resulting target proteins represent excellent probes for protein NMR analysis. However, as the side-chain resonances of these residues emerge in a narrow spectral range, signal overlap represents a severe limitation in the case of high-molecular-weight NMR probes. We present a protocol to eliminate leucine labeling by supplying the medium with unlabeled α-ketoisocaproate. The resulting spectra of a model protein exclusively feature valine signals of increased intensity, confirming the method to be a first example of independent valine and leucine labeling employing α-ketoacid precursor compounds.

Amino acid derivatives inhibiting extracellular matrix metalloproteinase and TNF alpha release

The invention concerns compounds of general formula (X) in which Y represents in particular —CONHOH, R1represents in particular a C1-C5alkyl group, AA represents an amino acid, or an amino acid sequence, and R3represents in particular a group of formula —NH—(CH2)2—SCH3. The invention also concerns the pharmaceutical compositions containing them, and the methods for obtaining them.

Dioxolanones as Synthetic Intermediates. Part 1. Synthesis of α-Keto Acids, α-Keto Aldehydes, and α-Ketols

2,2-Pentamethylene-1,3-dioxolan-4-one (10) has been elaborated to provide 5'-ylidene derivatives using a Wittig approach.This apparently novel class of compounds is subject to nucleophilic attack at the 4-position because of strain inherent in the 5-membered ring.Thus alkaline hydrolysis leads to the formation of α-keto acids; hydride reduction of dioxolanones incorporating conjugated aryl substituents using di-isobutylaluminium hydride leads to α-keto-aldehydes; the reaction of dioxolanone (15) with methylmagnesium iodide gave the α-ketol (40).