L-Pyroglutamic acid

Base Information

• Chemical Name: L-Pyroglutamic acid
• CAS No.: 98-79-3
• Deprecated CAS: 16891-48-8,29222-42-2,498-91-9,6886-28-8,87430-62-4,35255-51-7,312618-42-1,95650-42-3,29222-42-2,312618-42-1,498-91-9,6886-28-8,87430-62-4
• Molecular Formula: C5H7NO3
• Molecular Weight: 129.115
• Hs Code.: 29337900
• European Community (EC) Number: 202-700-3
• NSC Number: 760414,11742,9966
• UNII: SZB83O1W42
• DSSTox Substance ID: DTXSID6046260
• Nikkaji Number: J4.959J
• Wikipedia: Pyroglutamic_acid
• Wikidata: Q60998677
• NCI Thesaurus Code: C82933
• RXCUI: 9036
• Metabolomics Workbench ID: 37171
• ChEMBL ID: CHEMBL397976
• Mol file: 98-79-3.mol

Synonyms:5-Ketoproline;5-Oxoproline;5-Oxopyrrolidine-2-Carboxylic Acid;Magnesium Pidolate;Pidolate, Magnesium;Pidolic Acid;Pyroglutamate;Pyroglutamic Acid;Pyrrolidonecarboxylic Acid

Chemical Property of L-Pyroglutamic acid

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 1.79E-09mmHg at 25°C
• Melting Point: 160-163 °C(lit.)
• Refractive Index: -10 ° (C=5, H2O)
• Boiling Point: 453.1 °C at 760 mmHg
• PKA: 3.32(at 25℃)
• Flash Point: 227.8 °C
• PSA: 66.40000
• Density: 1.38 g/cm³
• LogP: -0.32160
• Storage Temp.: Store at RT.
• Solubility.: H2O: 1 M at 20 °C, clear, colorless
• Water Solubility.: 10-15 g/100 mL (20 ºC)
• XLogP3: -0.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 129.042593085
• Heavy Atom Count: 9
• Complexity: 154

Purity/Quality:

98% ^*data from raw suppliers

L-Pyroglutamic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Amino Acids and Derivatives
• Canonical SMILES: C1CC(=O)NC1C(=O)O
• Isomeric SMILES: C1CC(=O)N[C@@H]1C(=O)O
• Uses: L-Pyroglutamic acid is used in the synthesis of:Nonproteinogenic amino acids such as (3S,4R)-3,4-dimethyl-L-pyroglutamic acid and (3S,4R)-3,4-dimethyl-L-glutamine.Chiral N-heterocyclic carbenes (NHCs) as catalysts for the asymmetric dimerization of alkylarylketenes to give the corresponding α-quaternary β-alkylidenyl-β-lactones.It is also used in the total synthesis of (?)-stemoamide and celogentin C.It can be used as a kind of intermediates of organic synthesis as well as food additives.It is used in food, medicine, cosmetics and other industries. L-Pyroglutamic acid is an amino acid that is used in the synthesis of peptides. It has also been observed to convert when placed at the N-terminus in vivo to create IgG2 antibodies. A building block for pharmaceuticals and asymmetric synthesis In the resolution of racemic amines.
• Production method: There are semi-synthetic methods, enzymatic conversion method and total synthesis method. Currently the major approach of industrial production is the semi-synthetic method with glutamic acid being the raw material. Have the 42% of glutamic acid solution heated at 140 °C for 3h to obtain the reaction solution with L-pyroglutamic acid being the major component. The reaction solution further undergoes concentration under reduced pressure, crystallization, washing, and drying to obtain the L-pyroglutamic acid with the conversion rate being 94%.

Technology Process of L-Pyroglutamic acid

There total 51 articles about L-Pyroglutamic acid 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: 95.0%

L-glutamic acid (56-86-0,21675-62-7,23009-64-5,25104-13-6,84960-48-5,25513-46-6) → L-Pyroglutamic acid (98-79-3)

Guidance literature:

With water; for 16h; Heating;

DOI:10.1002/recl.19921111204

Reference yield: 91.0%

L-N-t-butoxycarbonylpyroglutamic acid (53100-44-0,160347-90-0) → L-Pyroglutamic acid (98-79-3)

Guidance literature:

With silica gel; In dichloromethane; for 0.0166667h; Irradiation;

DOI:10.1055/s-1998-1604

Reference yield: 90.0%

tert-butyl (S)-N-tert-butoxycarbonylpyroglutamate (91229-91-3) → L-Pyroglutamic acid (98-79-3)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 0.333333h; Ambient temperature;

upstream raw materials:

D-Glutamic acid

L-glutamic acid

(S)-2-Amino-pentanedioic acid 5-ethyl ester

diethyl 2-aminopentanedioate

Downstream raw materials:

L-pyroglutamyl-L-histidine (N^im-trityl) methyl ester

(2R,5S)-2-t-butyl-1-aza-3-oxabicyclo<3.3.0>octane-4,8-dione

(3R,4R,7R,10S)-1-aza-3-pyroglutamoylamino-4-phenyl-10-carbomethoxybicyclo[5.3.0]decane

Pyr-His-Pro-NH₂

Refernces

• 1、 Gowda, G. A. Nagana,Gowda, Yashas N.,Raftery, Daniel. "Massive Glutamine Cyclization to Pyroglutamic Acid in Human Serum Discovered Using NMR Spectroscopy". . p. 3800 - 3805. Retrieved 2015.
• 2、 -. "Preparation method of (S)-1 - (benzyloxycarbonyl) -5 -oxo-pyrrolidine -2 - formic acid". Paragraph 0044. . Retrieved 2021/09/01.
• 3、 Einat, H.,Grinberg, I.,Lugasi, L.,Margel, S.,Okun, E.,Rudnick-Glick, S.. "Designed proteinoid polymers and nanoparticles encapsulating risperidone for enhanced antipsychotic activity". . . Retrieved 2020/10/28.