3-Oxopentanoic acid

Base Information

• Chemical Name: 3-Oxopentanoic acid
• CAS No.: 10191-25-0
• Molecular Formula: C5H8 O3
• Molecular Weight: 116.117
• Hs Code.: 2918300090
• UNII: 090PW368EP
• DSSTox Substance ID: DTXSID50331432
• Nikkaji Number: J206.092B
• Wikipedia: 3-Oxopentanoic_acid
• Wikidata: Q2823218
• Metabolomics Workbench ID: 1529
• Mol file: 10191-25-0.mol

Synonyms:3-Oxopentanoic acid;10191-25-0;3-oxovaleric acid;Pentanoic acid, 3-oxo-;3-oxo-pentanoic acid;3-Oxopentanoicacid;beta-Ketopentanoate;3-Ketovaleric acid;3-keto valeric acid;3-oxidanylidenepentanoic acid;090PW368EP;MFCD11040434;3-oxovalerate;Propionylacetic Acid;3-Ketopentanoic Acid;QT8;SCHEMBL24358;UNII-090PW368EP;CHEBI:27401;DTXSID50331432;LMFA01060005;AKOS006306797;AM85448;CS-0321524;FT-0673435;C02233;Q2823218

Chemical Property of 3-Oxopentanoic acid

Chemical Property:

• Vapor Pressure: 0.0143mmHg at 25°C
• Melting Point: 65-66 °C (decomp)(Solv: ethyl ether (60-29-7); hexane (110-54-3))
• Refractive Index: 1.434
• Boiling Point: 238.6°C at 760 mmHg
• PKA: 3.51±0.32(Predicted)
• Flash Point: 112.3°C
• PSA: 54.37000
• Density: 1.129g/cm³
• LogP: 0.44020
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 116.047344113
• Heavy Atom Count: 8
• Complexity: 106

Purity/Quality:

98%,99%, ^*data from raw suppliers

3-OxopentanoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(=O)CC(=O)O
• Uses: Urinary metabolite of isoleucine found in patients with methylmalonic and proprionic acidemia.

Technology Process of 3-Oxopentanoic acid

There total 10 articles about 3-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: 95.0%

methyl propanoyl acetate (30414-53-0) → 3-oxo-valeric acid (10191-25-0)

Guidance literature:

With sodium hydroxide; at 25 ℃; for 24h;

Reference yield: 76.0%

ethyl propanoylacetate (4949-44-4) → 3-oxo-valeric acid (10191-25-0)

Guidance literature:

With sodium hydroxide; for 30h; Ambient temperature;

DOI:10.1021/jo9721610

Reference yield:

cycl-isopropylidene malonate (2033-24-1) + propionic acid (802294-64-0,79-09-4) → 3-oxo-valeric acid (10191-25-0)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 ℃; for 16h; Inert atmosphere;

DOI:10.1021/ol400926p

upstream raw materials:

α-ketoglutaric acid

3-hydroxyvaleric acid

methyl propanoyl acetate

t-Butyl 3-oxopentanoate

Downstream raw materials:

methyl propanoyl acetate

2-oxo-butyraldehyde-(4-nitro-phenylhydrazone)

4-methyl-5-oxo-3-phenyl-cyclohex-3-enecarboxylic acid

1-hydroxy-1-(4-nitrophenyl)-pentan-3-one

Refernces

• 1、 Blaisse, Michael R.,Dong, Hongjun,Fu, Beverly,Chang, Michelle C. Y.. "Discovery and Engineering of Pathways for Production of α-Branched Organic Acids". . p. 14526 - 14532. Retrieved 2017.
• 2、 Kourouli, Therapia,Kefalas, Panagiotis,Ragoussis, Nikitas,Ragoussis, Valentine. "A new protocol for a regioselective aldol condensation as an alternative convenient synthesis of β-ketols and α,β-unsaturated ketones". . p. 4615 - 4618. Retrieved 2002.
• 3、 -. "Antibacterial agents: high-potency myxopyronin derivatives". Page/Page column 25-26; 37. . Retrieved 2016/03/12.
• 4、 Bradshaw, Ben,Parra, Claudio,Bonjoch, Josep. "Organocatalyzed asymmetric synthesis of morphans". supporting information. p. 2458 - 2461. Retrieved 2013/06/27.