DL-Proline

Base Information

• Chemical Name: DL-Proline
• CAS No.: 609-36-9
• Molecular Formula: C5H9NO2
• Molecular Weight: 115.132
• Hs Code.: 2922.49
• European Community (EC) Number: 210-189-3
• NSC Number: 97923,46703
• UNII: DCS9E77JPQ
• DSSTox Substance ID: DTXSID9041104
• Nikkaji Number: J1.287D
• Wikidata: Q484583
• NCI Thesaurus Code: C61732
• ChEMBL ID: CHEMBL72275
• Mol file: 609-36-9.mol

Synonyms:poly(DL-proline);poly(L-proline);polyproline

Chemical Property of DL-Proline

Chemical Property:

• Melting Point: 208 °C (dec.)(lit.)
• Refractive Index: 1.4538 (estimate)
• Boiling Point: 252.2 °C at 760 mmHg
• PKA: 2.35±0.20(Predicted)
• Flash Point: 106.3 °C
• Density: 1.187 g/cm³
• Storage Temp.: Store at RT.
• Solubility.: Methanol, Water
• Water Solubility.: SOLUBLE
• 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

DL-Proline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 22-24/25-36/37/39-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Amino Acids and Derivatives
• Canonical SMILES: C1CC(NC1)C(=O)O
• Uses: DL-Proline is the racemic mixture of both L-Proline (P755995) and D-Proline (P755990).

Technology Process of DL-Proline

There total 97 articles about DL-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: 100.0%

Methyl 1-(trichloroacetyl)-2-pyrrolidinecarboxylate (138286-85-8) → rac-Pro-OH (609-36-9,25191-13-3,37159-97-0,4305-67-3,4607-28-7)

Guidance literature:

With potassium hydroxide; In methanol; Ambient temperature;

DOI:10.1021/jo00031a052

Reference yield: 95.0%

pyrrole-2-carboxyl acid (634-97-9) → rac-Pro-OH (609-36-9,25191-13-3,37159-97-0,4305-67-3,4607-28-7)

Guidance literature:

With 10% Rh/C; hydrogen; In isopropyl alcohol; at 60 ℃; for 8h; under 3800.26 Torr;

DOI:10.1002/chem.200900361

Reference yield: 94.0%

acetonitrile (75-05-8,26809-02-9) + N-carbobenzyloxyproline (1148-11-4) → N-(phenylmethyl)acetamide (588-46-5) + rac-Pro-OH (609-36-9,25191-13-3,37159-97-0,4305-67-3,4607-28-7)

Guidance literature:

With trifluoroacetic anhydride; at 80 ℃; for 5h; Yields of byproduct given;

DOI:10.1039/a708294k

upstream raw materials:

3,3-dichloro-piperidin-2-one

aminomalonic acid diethyl ester

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

Glutamic acid

Downstream raw materials:

pyrrolidine

4-amino-n-butyric acid

5-aminopentanoic acid

valeric acid

Refernces

The First Thermodynamic Data on the Complexation of Amino Acids with Cryptand 222 in Methanol at 298.15 K

10.1039/C39900000116

The research investigates the interaction between the macrobicyclic ligand cryptand 222 and various amino acids in methanol. The study aims to provide the first thermodynamic data on the formation of 1:1 complexes between cryptand 222 and amino acids, including glycine, DL-alanine, DL-phenylalanine, DL-serine, DL-proline, and DL-tryptophan, at 298.15 K. Using titration calorimetry and potentiometric titration, the researchers determined the stability constants (log Ks), Gibbs free energy (ΔG°), enthalpy (ΔH°), and entropy (ΔS°) of these complexation reactions. The results indicate that the amino group of the amino acids is the primary active site for interaction with cryptand 222, and the stability of the complexes is influenced by steric factors from substituent groups on the α-carbon of the amino acids. The study concludes that complexation is enthalpically and entropically favored for most amino acids, except glycine. Additionally, computer modeling suggests that the interaction occurs through hydrogen bonds and electrostatic interactions between the amino group and the oxygen atoms of cryptand 222. The findings have implications for understanding the transport of amino acids across cell membranes, enhancing their solubility in organic solvents, and developing methods for their separation.