Proline

Base Information

• Chemical Name: Proline
• CAS No.: 37159-97-0
• Deprecated CAS: 7005-20-1,1150316-19-0,95650-41-2,18875-45-1,4607-28-7,1150316-19-0,95650-41-2
• Molecular Formula: C₅H₉NO₂
• Molecular Weight: 115.132
• European Community (EC) Number: 205-702-2,925-434-6
• NSC Number: 760114
• UNII: 9DLQ4CIU6V
• DSSTox Substance ID: DTXSID5044021
• Nikkaji Number: J9.117K
• Wikipedia: Proline
• Wikidata: Q20035886
• NCI Thesaurus Code: C29612
• RXCUI: 8737
• Metabolomics Workbench ID: 37110
• ChEMBL ID: CHEMBL54922
• Mol file: 37159-97-0.mol

Synonyms:L Proline;L-Proline;Proline

Chemical Property of Proline

Chemical Property:

• Boiling Point: 252.187 °C at 760 mmHg
• Flash Point: 106.319 °C
• Density: 1.186 g/cm³
• Storage Temp.: 2-8°C
• XLogP3: -2.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 115.063328530
• Heavy Atom Count: 8
• Complexity: 103

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s): R
• Hazard Codes: R

MSDS Files:

Useful:

• Chemical Classes: Biological Agents -> Amino Acids and Derivatives
• Canonical SMILES: C1CC(NC1)C(=O)O
• Isomeric SMILES: C1C[C@H](NC1)C(=O)O
• Recent ClinicalTrials: The Effect of a Vegan Alginate Product on Athletes Recovery and Performance
• Recent EU Clinical Trials: Prevention of preterm birth in women at risk identified by ultrasound: evaluation of two

Technology Process of Proline

There total 516 articles about 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: 62.0%

(3R,8aS)-hexahydro-3-(prop-2-enyl)pyrrolo[1,2-a]pyrazine-1,4-dione (205875-07-6) → D-allylglycine (54594-06-8) + L-proline (147-85-3,25191-13-3,37159-97-0,4305-67-3,4607-28-7)

Guidance literature:

With hydrogenchloride; at 90 ℃; for 10h;

DOI:10.1016/S0040-4020(98)00081-7

Reference yield: 1.8%

pyrrolidine (123-75-1) + formic acid (64-18-6) → pyrrolidine-3-carboxylic acid (59378-87-9,68464-02-8,72580-53-1,72580-54-2) + glycine (56-40-6,18875-39-3,25718-94-9) + rac-Pro-OH (609-36-9,25191-13-3,37159-97-0,4305-67-3,4607-28-7)

Guidance literature:

In water; at 10 - 20 ℃; for 1h; contact glow discharge electrolysis (500-600 V, 45 mA);

Reference yield: 0.4%

pyrrolidine (123-75-1) + sodium formate (141-53-7) → pyrrolidine-3-carboxylic acid (59378-87-9,68464-02-8,72580-53-1,72580-54-2) + glycine (56-40-6,18875-39-3,25718-94-9) + rac-Pro-OH (609-36-9,25191-13-3,37159-97-0,4305-67-3,4607-28-7)

Guidance literature:

In water; at 10 - 20 ℃; for 1h; contact glow discharge electrolysis (500-600 V, 45 mA);

upstream raw materials:

3,3-dichloro-piperidin-2-one

aminomalonic acid diethyl ester

(+/-)-5-amino-2-chloro-valeric acid

Glutamic acid

Downstream raw materials:

(S)-proline-N-carboxyanhydride

N-methyl-L-proline

1-hippuroyl-L-proline

optically inactive 1-valyl-proline

Refernces

• 1、 De Cesare, Silvia,McKenna, Catherine A.,Mulholland, Nicholas,Murray, Lorna,Bella, Juraj,Campopiano, Dominic J.. "Direct monitoring of biocatalytic deacetylation of amino acid substrates by1H NMR reveals fine details of substrate specificity". supporting information. p. 4904 - 4909. Retrieved 2021/06/16.
• 2、 Iwasaki, Arihiro,Ohtomo, Keisuke,Kurisawa, Naoaki,Shiota, Ikuma,Rahmawati, Yulia,Jeelani, Ghulam,Nozaki, Tomoyoshi,Suenaga, Kiyotake. "Isolation, Structure Determination, and Total Synthesis of Hoshinoamide C, an Antiparasitic Lipopeptide from the Marine Cyanobacterium Caldora penicillata". . p. 126 - 135. Retrieved 2021/01/13.