4-Methyl-2-oxopentanoic acid

Base Information

• Chemical Name: 4-Methyl-2-oxopentanoic acid
• CAS No.: 816-66-0
• Molecular Formula: C6H10O3
• Molecular Weight: 130.144
• European Community (EC) Number: 212-435-5
• UNII: 4GUJ8AH400
• DSSTox Substance ID: DTXSID6061157
• Nikkaji Number: J39.557I
• Wikipedia: Alpha-Ketoisocaproic_acid
• Wikidata: Q622421
• Metabolomics Workbench ID: 37370
• ChEMBL ID: CHEMBL445647
• Mol file: 816-66-0.mol

Synonyms:2-keto-4-methylvalerate;2-ketoisocaproate;2-oxo-4-methylpentanoic acid;2-oxo-4-methylvaleric acid;2-oxoisocaproic acid;4-methyl-2-oxopentanoate;4-methyl-2-oxopentanoic acid;4-methyl-2-oxovalerate;alpha-keto-isocaproic acid;alpha-ketoisocaproate;alpha-ketoisocaproic acid;alpha-ketoisocaproic acid, calcium salt;alpha-ketoisocaproic acid, sodium salt;alpha-oxoisocaproate;ketoleucine

Chemical Property of 4-Methyl-2-oxopentanoic acid

Chemical Property:

• Vapor Pressure: 0.00269mmHg at 25°C
• Melting Point: 8-10 °C
• Refractive Index: n20/D 1.431
• Boiling Point: 265.2 °C at 760 mmHg
• PKA: 2.65±0.54(Predicted)
• Flash Point: 128.5 °C
• Density: 1.085 g/cm³
• Storage Temp.: 2-8°C
• Water Solubility.: Soluble in water.
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 130.062994177
• Heavy Atom Count: 9
• Complexity: 126

Purity/Quality:

99% ^*data from raw suppliers

4-Methyl-2-oxovaleric Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)CC(=O)C(=O)O
• Uses: 4-Methyl-2-oxovaleric acid is an intermediate in the metabolism of leucine and also used as flavoring agents.

Technology Process of 4-Methyl-2-oxopentanoic acid

There total 63 articles about 4-Methyl-2-oxopentanoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

ethyl 4-methyl-2-oxopentanoate (26073-09-6) → 4-methyl-2-oxopentanoic acid (816-66-0)

Guidance literature:

With potassium hydroxide; In water; at 100 ℃; Inert atmosphere;

DOI:10.3762/bjoc.9.200

Reference yield: 97.0%

4-hydroxy-4-isobutyl-3-phenylisoxazoline-5-one (80490-45-5) → 4-methyl-2-oxopentanoic acid (816-66-0) + benzonitrile (100-47-0)

Guidance literature:

With 2,6-dichloro-benzonitrile; In benzene; for 1h; Heating;

Reference yield: 97.0%

4-methyl-2-oxo-pentanoic acid methyl ester (3682-43-7) → 4-methyl-2-oxopentanoic acid (816-66-0)

Guidance literature:

With water; sodium hydroxide; In methanol; at 0 - 60 ℃; for 1.5h;

DOI:10.1002/ejoc.202000294

upstream raw materials:

α-ketoglutaric acid

L-leucine

LEUCINE

4-methyl-2-oxo-valeric acid amide

Downstream raw materials:

(R)-leucine

isovaleraldehyde

(R)-2-hydroxy-4-methylpentanoic acid

Refernces

• 1、 Orrego, Alejandro H.,López-Gallego, Fernando,Espaillat, Akbar,Cava, Felipe,Guisan, José M.,Rocha-Martin, Javier. "One-step Synthesis of α-Keto Acids from Racemic Amino Acids by A Versatile Immobilized Multienzyme Cell-free System". . p. 3002 - 3011. Retrieved 2018.
• 2、 Yamada, Tohru,Kakinuma, Katsumi,Endo, Toyoshige,Oshima, Tairo. "Stereospecificity of the Hydride Transfer Reaction Catalyzed by Isopropylmalate Dehydrogenase of Thermophilic Bacteria Thermus thermophilius". . p. 1749 - 1752. Retrieved 1987.
• 3、 Matsunami,Kawaguchi,Inagaki,Eguchi,Kakinuma,Tanaka. "Overproduction and substrate specificity of 3-isopropylmalate dehydrogenase from Thiobacillus ferrooxidans.". . p. 372 - 373. Retrieved 1998.
• 4、 Buller, Andrew R.,Doyon, Tyler J.,Grieger, Abbigail M.,Kim, Maeve,Kumar, Prasanth,Madigan, Cormac,Stitgen, Abigail,Thein, Sierra,Willoughby, Patrick H.. "Scalable and Selective β-Hydroxy-α-Amino Acid Synthesis Catalyzed by Promiscuous l-Threonine Transaldolase ObiH". . . Retrieved 2021/11/23.
• 5、 Barber, David M.,D?ller, Uwe,Dietrich, Hansj?rg,Hoffmann, Michael G.,Kocakaya, Tamer,Kuhn, Birgit,Maier, Martin E.,Morkunas, Marius,Schmutzler, Dirk,Schnatterer, Stefan. "Total Synthesis of the Natural Herbicide MBH-001 and Analogues". . p. 2271 - 2290. Retrieved 2020/04/23.