3-Methyl-2-oxovaleric acid

Base Information

• Chemical Name: 3-Methyl-2-oxovaleric acid
• CAS No.: 1460-34-0
• Deprecated CAS: 39748-49-7
• Molecular Formula: C6H10O3
• Molecular Weight: 130.144
• Hs Code.: 2918300090
• European Community (EC) Number: 215-955-0
• UNII: 787T50HCIV
• DSSTox Substance ID: DTXSID50862670
• Nikkaji Number: J39.560I
• Wikidata: Q23905808
• Metabolomics Workbench ID: 78504
• Mol file: 1460-34-0.mol

Synonyms:2-keto methylvalerate;2-keto-3-methylvaleric acid;2-oxo-3-methylvalerate;3-methyl-2-oxopentanoate;alpha-keto-beta-methyl-n-valeric acid;alpha-keto-beta-methylvalerate;alpha-keto-beta-methylvaleric acid;alpha-keto-beta-methylvaleric acid, (+-)-isomer;alpha-keto-beta-methylvaleric acid, (S)-isomer;alpha-keto-beta-methylvaleric acid, calcium salt;alpha-keto-beta-methylvaleric acid, calcium salt, (S)-isomer;alpha-keto-beta-methylvaleric acid, monosodium salt, (S)-isomer;alpha-keto-beta-methylvaleric acid, sodium salt;alpha-keto-beta-methylvaleric acid, sodium salt, (+-)-isomer;KMVA

Chemical Property of 3-Methyl-2-oxovaleric acid

Chemical Property:

• Appearance/Colour: Colorless to pale yellow liquid
• Vapor Pressure: 0.239mmHg at 25°C
• Melting Point: 42°C
• Boiling Point: 190.5 °C at 760 mmHg
• PKA: 2.65±0.54(Predicted)
• Flash Point: 83.3 °C
• PSA: 54.37000
• Density: 1.087 g/cm³
• LogP: 0.68620
• Storage Temp.: Refrigerator
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 130.062994177
• Heavy Atom Count: 9
• Complexity: 128

Purity/Quality:

99% ^*data from raw suppliers

3-Methyl-2-oxovaleric Acid >95.0%(GC)(T) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-36
• Safety Statements: 26-36/37/39-36

MSDS Files:

Useful:

• Canonical SMILES: CCC(C)C(=O)C(=O)O

Technology Process of 3-Methyl-2-oxovaleric acid

There total 40 articles about 3-Methyl-2-oxovaleric 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%

4-(sec-butyl)-2-(trifluoromethyl)oxazol-5(2H)-one (2546-69-2) → 2-oxo-3(RS)-methylvaleric acid (1460-34-0)

Guidance literature:

With sodium hydroxide; In water; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1021/jo102228j

Reference yield: 90.0%

L-isoleucine (73-32-5,959215-79-3,18875-42-8) → 3-methyl-2-oxopentanoic acid (1460-34-0,39748-49-7,61748-89-8,24809-08-3)

Guidance literature:

L-isoleucine; With trifluoroacetic anhydride; at 65 ℃; for 36h;

With trifluoroacetic acid; In water;

DOI:10.1021/acs.joc.8b01420

Reference yield: 87.7%

2-Methylbutyraldehyde (96-17-3,57456-98-1) + oxalic acid diethyl ester (95-92-1) → 2-oxo-3(RS)-methylvaleric acid (1460-34-0)

Guidance literature:

oxalic acid diethyl ester; With sodium methylate; In methanol; at 25 ℃; for 0.5h; Large scale;

2-Methylbutyraldehyde; With water; sodium hydroxide; In methanol; at 25 ℃; for 5.5h; Large scale;

With hydrogenchloride; In methanol; for 0.5h; Reagent/catalyst; Solvent; Large scale;

upstream raw materials:

L-isoleucine

D-Isoleucine

ethyl 4-methyl-2-oxopentanoate

diethyl 2-ethyl-2-methyl-3-oxobutanedioate

Downstream raw materials:

(Z)-methyl 2-(((benzyloxy)carbonyl)amino)-3-methylpent-2-enoate

isoleucine

α-hydroxy-β-methyl-n-valeric acid

(S)-2-[(S)-3-{3-[(S)-3-((1R,2R)-2-Benzyloxycarbonylamino-1,3-dihydroxy-propyl)-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-7-yl]-4-hydroxy-phenyl}-2-(3-methyl-2-oxo-pentanoylamino)-propionylamino]-succinamic acid benzyl ester

Refernces

• 1、 Hashiguchi, Ken-Ichi,Takesada, Hiroko,Suzuki, Eiichiro,Matsui, Hiroshi. "Construction of an L-isoleucine overproducing strain of Escherichia coli K-12". . p. 672 - 679. Retrieved 1999.
• 2、 Zhang, Shuaibing,Huang, Ying,He, Shijun,Chen, Heping,Wu, Bin,Li, Shanyong,Zhao, Zhenzhu,Li, Zhenghui,Wang, Xian,Zuo, Jianping,Feng, Tao,Liu, Jikai. "Heterocyclic Compounds from the Mushroom Albatrellus confluens and Their Inhibitions against Lipopolysaccharides-Induced B Lymphocyte Cell Proliferation". . p. 10158 - 10165. Retrieved 2018.
• 3、 Metzler,Snell. "-". . p. 979,981. Retrieved 1952.
• 4、 Pickl, Mathias,Marín-Valls, Roser,Joglar, Jesús,Bujons, Jordi,Clapés, Pere. "Chemoenzymatic Production of Enantiocomplementary 2-Substituted 3-Hydroxycarboxylic Acids from l-α-Amino Acids". . p. 2866 - 2876. Retrieved 2021/04/14.