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

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

Uses

Used in Analytical Chemistry:
Sodium ketoisocaproate is used as a quantification agent for branched-chain keto acids from cell extracts in the high-performance liquid chromatography-fluorescence (HPLC-fluorescence) method. This application is crucial for the accurate measurement and analysis of these acids in various biological samples.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Sodium ketoisocaproate is used as an intermediate in the metabolism of leucine, an essential branched-chain amino acid. Its role in the metabolic process makes it a valuable compound for the development of drugs and therapies targeting leucine metabolism-related conditions.
Used in Food Industry:
Sodium ketoisocaproate is found in various food items, such as fruits, vegetables, and dairy products. Its presence in these food sources contributes to their nutritional value and may play a role in the overall health benefits associated with their consumption.

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

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

Downstream Products

• 328-38-1 (R)-leucine 
• 61-90-5 L-leucine 
• 96136-13-9 4-methyl-2-oxo-pentanoic phenylmethyl ester acid 
• 1266250-07-0 CoI(C₅(CH₃)5)(OOCC(CH₂CH(CH₃)2)NC₆H₄NNC₆H₄NH₂) 
• 59935-31-8 <(15)N>-L-leucine 
• 89836-92-0 (R)-α-deuterated leucine 
• 89836-93-1 (S)-α-deuterated leucine 
• 20312-37-2 (R)-2-hydroxy-4-methylpentanoic acid 
• 503-74-2 3-methylbutyric acid 
• 429661-38-1 C₂₀H₂₅Cl₂N₃O₄ 
• 429661-37-0 C₂₀H₂₅Cl₂N₃O₄ 
• 164400-78-6 [Ru(H)(CO)(P(C₆H₅)3)2(OOCC(CH₂CH(CH₃)2)N(CH₂C₆H₅))] 
• 128972-02-1 4-methyl-2-oxo-N-(2-oxo-2-phenylethyl)pentanamide 

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.

Preparation method of alpha-ketoleucine calcium dihydrate or alpha-ketophenylalanine calcium monohydrate

The invention discloses a preparation method of alpha-ketoleucine calcium dihydrate or alpha-ketophenylalanine calcium monohydrate. In an existing method, the quality of a final product is low, and the content of related substances is high. The method comprises the steps that isobutylidene hydantoin or benzal hydantoin is taken as a raw material and generates a pipeline continuous flow ring-opening reaction with an alcohol-water solution of alkali, and then corresponding alpha-ketoacid salt is obtained, wherein the pipeline continuous flow ring-opening reaction is a continuous ring-opening reaction conducted in a pipeline reactor; the obtained alpha-ketoacid salt is firstly extracted with a hydrocarbon solvent or a halohydrocarbon solvent or a ketone solvent or an ether solvent for impurity removal and then acidized to obtain a corresponding crude alpha-ketonic acid product, the crude alpha-ketonic acid product is extracted with the hydrocarbon solvent or the halohydrocarbon solvent or the ketone solvent or the ether solvent for impurity removal, and then a fine alpha-ketonic acid product is obtained; the obtained alpha-ketonic acid is prepared into calcium salt, crystallization is conducted, and the alpha-ketoacid calcium hydrate is obtained. Accordingly, the high-quality and high-purity alpha-ketoleucine calcium dihydrate and alpha-ketophenylalanine calcium monohydrate are obtained.

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.

Methods for the synthesis of L-leucine selectively labelled with carbon-13 or deuterium in either diastereotopic methyl group

A versatile approach is described for the enantioselective synthesis of isotopically labelled L-leucine involving the preparation of 4-methylpentanoic acid labelled selectively with carbon-13 or deuterium in either the pro-R or pro-S methyl group followed by a reductive amination of the ketone catalysed by leucine dehydrogenase. This strategy is applied to the total synthesis of (2S,4R)-[5,5,5-D3]-leucine using CD3I as the source of deuterium.

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).