Proline

Base Information

• Chemical Name: Proline
• CAS No.: 147-85-3
• 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
• Hs Code.: 2922.49
• 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: 147-85-3.mol

Synonyms:L Proline;L-Proline;Proline

Chemical Property of Proline

Chemical Property:

• Appearance/Colour: White crystalline powder
• Vapor Pressure: 0.00615mmHg at 25°C
• Melting Point: 228 °C (dec.)(lit.)
• Refractive Index: -85 ° (C=4, H2O)
• Boiling Point: 252.2 °C at 760 mmHg
• PKA: 1.95, 10.64(at 25℃)
• Flash Point: 106.3 °C
• PSA: 49.33000
• Density: 1.186 g/cm³
• LogP: 0.15180
• Storage Temp.: Store at RT.
• Sensitive.: Hygroscopic
• Solubility.: H2O: 50 mg/mL
• 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

L-Proline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 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
• 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
• Role in Plant Physiology: Metabolism and Growth: Important for maintaining plant metabolism and growth under abiotic stress conditions.; Abiotic Stress Tolerance: Accumulation of proline positively correlates with plant tolerance to various abiotic stresses.; Functions: Acts as a metal chelator, molecular chaperone, antioxidative defense molecule, osmoprotectant, nitrogen and carbon source, and signaling molecule in plants.
• Chemical Properties and Enzymatic Specificity: Chirality: Proline exists as L and D enantiomers, with living cells predominantly metabolizing the L-proline form.; Organocatalyst: Used in synthesizing enantiopure drugs and as a chemical chaperone for cryopreserving living cells.; Enzymatic Specificity: Enzymes involved in proline biosynthesis and oxidation are highly specific.
• Role in Human Proteome: Concentration: L-Proline residues constitute nearly 6% of the human proteome, mainly found in L-Pro-rich proteins.; Antimicrobial Peptides: Proline-rich antimicrobial peptides (PrAMPs) play a role in innate immunity and defense against infections.
• Metabolic Functions: Energy Source: Mitochondrial oxidation of proline provides ATP/energy for various cell types, including flight muscle cells, protozoan parasites, and cancer cells.; Metabolite Production: Proline serves as a precursor for polyamines, citrate, L-glutamate, and gamma-aminobutyric acid (GABA) in different metabolic pathways.
• Protective Effects and Cellular Functions: ROS Protection: Protects human cells against ROS-mediated oxidative stress.; Neurotransmitter Precursor: Precursor for major neurotransmitters L-glutamate and GABA in the mammalian brain.; Epigenetic Modifier: Functions as an epigenetic modifier.; Cell Proliferation and Plasticity: Induces proliferation of stem and cancer cells and controls cell plasticity.; Signaling Molecule: Acts as a signal, modulating gene expression and metabolic processes.

Technology Process of Proline

There total 374 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:

(S)-Pyrrolidine-1,2-dicarboxylic acid 1-[2-(4-methoxy-phenyl)-2-oxo-ethyl] ester (125219-04-7) → 1-(4-methoxyphenyl)ethanone (100-06-1) + L-proline (147-85-3,25191-13-3,37159-97-0,4305-67-3,4607-28-7)

Guidance literature:

Irradiation; mild conditions;

DOI:10.1016/S0040-4039(00)99608-4

Reference yield:

(S)-N-(4-nitrophenyl)pyrrolidine-2-carboxamide (64155-02-8,7369-91-7) → 4-nitro-aniline (100-01-6,104810-17-5) + L-proline (147-85-3,25191-13-3,37159-97-0,4305-67-3,4607-28-7)

Guidance literature:

With Tris-HCl buffer; an aminopeptidase from the seeds of Cannabis sativa; water; at 37 ℃; pH=7.5; Enzyme kinetics; Enzymatic reaction;

DOI:10.1271/bbb.64.1055

upstream raw materials:

L-N-tosyl-proline

N-(3,5-dinitrobenzoyl)-L-proline

(S)-N-(naphthalen-2-yl)pyrrolidine-2-carboxamide

L-ornithine

Downstream raw materials:

1-[1-(toluene-4-sulfonyl)-L-prolyl]-L-proline

methyl (2S)-pyrrolidine carboxylate

(S)-acetylproline

(S)-proline-N-carboxyanhydride

Refernces

• 1、 Al-Awadhi, Fatma H.,Ratnayake, Ranjala,Paul, Valerie J.,Luesch, Hendrik. "Tasiamide F, a potent inhibitor of cathepsins D and E from a marine cyanobacterium". . p. 3276 - 3282. Retrieved 2016.
• 2、 Han, Jing,Huang, Maobo,Wang, Zhe,Zheng, Yuqing,Zeng, Guangzhi,He, Wenjun,Tan, Ninghua. "Cyclopentapeptides from Dianthus chinensis". . p. 550 - 553. Retrieved 2015.
• 3、 Phillips, Dennis R.,Uramoto, Masakazu,Isono, Kiyoshi,McCloskey, James A.. "Structure of the Antifungal Nucleotide Antibiotic Phosmidosine". . p. 854 - 859. Retrieved 1993.
• 4、 Angadi, Mahantesh A.,Tuwar, Suresh M.. "Kinetics and mechanism of oxidation of captopril by diperiodatocuprate(III) in aqueous alkaline medium". . p. 219 - 229. Retrieved 2015.
• 5、 Patel, Ramesh N.,Nanduri, Venkata,Brzozowski, David,McNamee, Clyde,Banerjee, Amit. "Enantioselective Enzymatic Cleavage of N-Benzyloxycarbonyl Groups". . p. 830 - 834. Retrieved 2003.
• 6、 Murata, Makoto,Hara, Takayoshi,Mori, Kohsuke,Ooe, Masahiko,Mizugaki, Tomoo,Ebitani, Kohki,Kaneda, Kiyotomi. "Efficient deprotection of N-benzyloxycarbonyl group from amino acids by hydroxyapatite-bound Pd catalyst in the presence of molecular hydrogen". . p. 4981 - 4984. Retrieved 2003.
• 7、 Hu, Xiaoyun,Chang, Qing,Shan, Zixing. "An improved and practical approach to essentially enantiopure BINOLs: Enantioselective inclusion complexation of (S)-proline". . p. 1327 - 1331,5. Retrieved 2012.
• 8、 Rogozhin,Davankov. "-". . p. 490. Retrieved 1971.
• 9、 Fernández, Rogelio,Bayu, Asep,Hadi, Tri Aryono,Bueno, Santiago,Pérez, Marta,Cuevas, Carmen,Putra, Masteria Yunovilsa. "Unique polyhalogenated peptides from the marine sponge Ircinia sp.". . . Retrieved 2020.
• 10、 Pham, Viet-La?,Gouzy-Darmon, Cécile,Pernier, Julien,Hanquez, Chantal,Hook, Vivian,Beinfeld, Margery C.,Nicolas, Pierre,Etchebest, Catherine,Foulon, Thierry,Cadel, Sandrine. "Mutation in the substrate-binding site of aminopeptidase B confers new enzymatic properties". . p. 730 - 741. Retrieved 2011.