4-Hydroxyproline

Base Information

• Chemical Name: 4-Hydroxyproline
• CAS No.: 49761-17-3
• Molecular Formula: C5H9 N O3
• Molecular Weight: 131.131
• NSC Number: 524341,122285,206304,206274,206273
• DSSTox Substance ID: DTXSID60861573
• Nikkaji Number: J4.116E
• Wikidata: Q411237
• ChEMBL ID: CHEMBL1213475
• Mol file: 49761-17-3.mol

Synonyms:4 Hydroxyproline;4-Hydroxyproline;cis 4 Hydroxyproline;cis-4-Hydroxyproline;Hydroxyproline;Oxyproline

Chemical Property of 4-Hydroxyproline

Chemical Property:

• Boiling Point: 355.2°Cat760mmHg
• Flash Point: 168.6°C
• PSA: 69.56000
• Density: 1.395g/cm³
• LogP: -0.87740
• XLogP3: -3.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 131.058243149
• Heavy Atom Count: 9
• Complexity: 125

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Amino Acids and Derivatives
• Canonical SMILES: C1C(CNC1C(=O)O)O

Technology Process of 4-Hydroxyproline

There total 23 articles about 4-Hydroxyproline 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:

2-oxo-5-phthalimidomethyl-tetrahydro-furan-3-carbonitrile (408539-58-2) → trans-4-hydroxy-D,L-proline (618-28-0,30724-02-8) + cis-4-hydroxyproline (49761-17-3,30724-02-8)

Guidance literature:

With sulfuryl dichloride; acetic acid; at 70 ℃; Erhitzen des Reaktionsprodukts mit konz. wss. HCl und Essigsaeure und Erwaermen des danach erhaltenen Reaktionsprodukts mit wss. Ba(OH)2;

DOI:10.1021/ja01630a038

Reference yield:

2-oxo-5-phthalimidomethyl-tetrahydro-furan-3-carboxylic acid ethyl ester (6284-28-2) → trans-4-hydroxy-D,L-proline (618-28-0,30724-02-8) + cis-4-hydroxyproline (49761-17-3,30724-02-8)

Guidance literature:

With sulfuryl dichloride; acetic acid; at 70 ℃; Erhitzen des Reaktionsprodukts mit konz. wss. HCl und Essigsaeure und Erwaermen des danach erhaltenen Reaktionsprodukts mit wss. Ba(OH)2;

DOI:10.1021/ja01630a038

Reference yield:

3-chloro-5-chloromethyl-dihydro-furan-2-one (2584-72-7) → trans-4-hydroxy-D,L-proline (618-28-0,30724-02-8) + cis-4-hydroxyproline (49761-17-3,30724-02-8)

Guidance literature:

With ammonium hydroxide; at 100 ℃;

DOI:10.1021/ja01630a038

upstream raw materials:

3-chloro-5-chloromethyl-dihydro-furan-2-one

3-bromo-5-chloromethyl-dihydro-furan-2-one

5-bromomethyl-3-chloro-dihydro-furan-2-one

ethyl 2-acetamido-2-(ethoxycarbonyl)-4-pentenoate

Downstream raw materials:

cis-1-acetyl-4-hydroxy-DL-proline

trans-4-hydroxy-D,L-proline

rac-Pro-OH

4-Hydroxy-1-propyl-pyrrolidine-2-carboxylic acid