4-Oxo-L-proline

Base Information

• Chemical Name: 4-Oxo-L-proline
• CAS No.: 4347-18-6
• Molecular Formula: C5H7NO3
• Molecular Weight: 129.115
• Hs Code.: 2933990090
• European Community (EC) Number: 224-409-0
• DSSTox Substance ID: DTXSID20942014
• Nikkaji Number: J205.723I
• Wikidata: Q27102095
• Metabolomics Workbench ID: 50661
• Mol file: 4347-18-6.mol

Synonyms:4-ketoproline;4-ketoproline, (L)-isomer;4-oxo-L-proline;4-oxoproline

Chemical Property of 4-Oxo-L-proline

Chemical Property:

• Vapor Pressure: 1.42E-05mmHg at 25°C
• Refractive Index: 1.511
• Boiling Point: 341.8 °C at 760 mmHg
• PKA: 2.26±0.20(Predicted)
• Flash Point: 160.5 °C
• PSA: 66.40000
• Density: 1.38 g/cm³
• LogP: -0.66920
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: -3.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 129.042593085
• Heavy Atom Count: 9
• Complexity: 154

Purity/Quality:

99% ^*data from raw suppliers

(S)-4-oxopyrrolidine-2-carboxylicacid 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(NCC1=O)C(=O)O
• Isomeric SMILES: C1[C@H](NCC1=O)C(=O)O

Technology Process of 4-Oxo-L-proline

There total 4 articles about 4-Oxo-L-proline 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:

(2S,4S)-4-fluoropyrrolidine-2-carboxylic acid (2438-57-5,913820-71-0) → 4-oxo-L-proline (4347-18-6)

Guidance literature:

With hydrogenchloride; α-ketoglutaric acid; ammonium iron (II) sulfate; L-proline cis-3-hydroxylase type I; sodium L-ascorbate; In aq. buffer; at 21 ℃; for 14h; pH=6.5; Enzymatic reaction;

DOI:10.1016/j.bioorg.2019.103386

Reference yield:

1-benzyloxycarbonyl-4-keto-L-proline (64187-47-9) → 4-oxo-L-proline (4347-18-6)

Guidance literature:

With hydrogen bromide; acetic acid;

DOI:10.1021/ja01558a050

Reference yield:

4R-4-hydroxyproline (51-35-4,30724-02-8) → 4-oxo-L-proline (4347-18-6)

Guidance literature:

Multi-step reaction with 3 steps

1: aqueous NaOH

2: acetone; CrO₃; aqueous H₂SO₄

3: HBr; acetic acid

With chromium(VI) oxide; sodium hydroxide; sulfuric acid; hydrogen bromide; acetic acid; acetone;

DOI:10.1021/ja01558a050

upstream raw materials:

1-benzyloxycarbonyl-4-keto-L-proline

4R-4-hydroxyproline

(2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid

(2S,4S)-4-fluoropyrrolidine-2-carboxylic acid

Downstream raw materials:

hydroxy L-proline

4R-4-hydroxyproline

Refernces