D-Pyroglutamic acid

Base Information

• Chemical Name: D-Pyroglutamic acid
• CAS No.: 4042-36-8
• Molecular Formula: C5H7NO3
• Molecular Weight: 129.115
• Hs Code.: 29339900
• European Community (EC) Number: 223-735-0
• UNII: TQP297C4HN
• DSSTox Substance ID: DTXSID10193432
• Nikkaji Number: J53.019K
• Wikipedia: Pyroglutamic_acid
• Wikidata: Q421383
• Metabolomics Workbench ID: 50698
• ChEMBL ID: CHEMBL1235172
• Mol file: 4042-36-8.mol

Synonyms:D-Pyroglutamic acid;4042-36-8;5-oxo-D-proline;(R)-5-Oxopyrrolidine-2-carboxylic Acid;D-Pyr-OH;(2R)-5-oxopyrrolidine-2-carboxylic acid;D-Proline, 5-oxo-;(R)-(+)-2-Pyrrolidone-5-carboxylic acid;D-Pidolic acid;(+)-Pyroglutamic acid;D-5-Oxo-2-pyrrolidinecarboxylic acid;(+)-Pidolic acid;D-5-Pyrrolidone-2-carboxylic acid;MFCD00066212;D-(+)-Pyroglutamic Acid;TQP297C4HN;CHEBI:16924;EINECS 223-735-0;(+)-2-Pyrrolidone-5-carboxylic acid;5-Oxo-L-proline-d5;(R)-()-2-Pyrrolidone-5-carboxylic acid;pyroglutaminsaure;D-PyroGlu;D-5-Oxoproline;(R)-2-Pyrrolidone-5-carboxylic acid;(R)-pyroglutamic acid;Pyroglutamic acid, D-;D-Glutamic Acid Lactam;H-D-Pyr-OH;RecPGA 100k;RecPGA 373K;(+)-D-Pyroglutamic acid;(R)-(+)-2-Pyrrolidinone-5-Carboxylic Acid;Proline, 5-oxo-, D-;bmse000483;bmse000821;bmse000878;UNII-TQP297C4HN;SCHEMBL223918;CHEMBL1235172;DTXSID10193432;BCP09505;s3107;AKOS006238827;AKOS015923215;CS-W002304;HY-W002304;(R)-2-Pyrrolidinone-5-carboxylic Acid;NCGC00163340-01;DS-13756;AM20100078;P1354;EN300-54541;C02237;(R)-(+)-2-Pyrrolidone-5-carboxylic acid, 95%;Q421383;220C30ED-A76B-4FEA-A8DD-577CCEBEE7DE;Q-100462;F0001-2478;Z812534840

Chemical Property of D-Pyroglutamic acid

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 0.002mmHg at 25°C
• Melting Point: 155-162 °C
• Refractive Index: 10 ° (C=5, H2O)
• Boiling Point: 453.1 °C at 760 mmHg
• PKA: 3.48±0.20(Predicted)
• Flash Point: 227.8 °C
• PSA: 66.40000
• Density: 1.38 g/cm³
• LogP: -0.32160
• Storage Temp.: Store at 0-5°C
• Solubility.: Dimethylformamide, DMSO (Slightly), Methanol (Slightly), Water
• Water Solubility.: soluble
• 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:

99% ^*data from raw suppliers

(R)-2-Pyrrolidinone-5-carboxylicAcid ^*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:

• Canonical SMILES: C1CC(=O)NC1C(=O)O
• Isomeric SMILES: C1CC(=O)N[C@H]1C(=O)O
• Uses: Serves as a building block in the synthesis of diphthamide Serves as a building block in the synthesis of diphthamide.

Technology Process of D-Pyroglutamic acid

There total 10 articles about D-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%

(R)-5-hydroxymethylpyrrolidin-2-one (66673-40-3) → D-pyrrolidone-5-carboxylic acid (4042-36-8)

Guidance literature:

With oxygen; sodium hydrogencarbonate; platinum; In water; for 4h; Ambient temperature;

Reference yield: 45.0%

tert-butyl (4R,4'R,5'S)-4-amino-5-(3',4'-dimethyl-2'-oxo-5'-phenyl-1'-imidazolydinyl)-5-oxopentanoate (307304-62-7) → D-pyrrolidone-5-carboxylic acid (4042-36-8)

Guidance literature:

With water; In 1,4-dioxane; for 12h; Heating;

DOI:10.1021/jo000321t

Reference yield:

D-Glutamic acid (6893-26-1,21675-62-7,23009-64-5,25104-13-6,84960-48-5,25513-46-6) → D-pyrrolidone-5-carboxylic acid (4042-36-8)

Guidance literature:

With water; for 63h; Heating;

DOI:10.1002/hlca.19900730113

upstream raw materials:

D-Glutamic acid

(R)-5-hydroxymethylpyrrolidin-2-one

L-Pyroglutamic acid

tert-butyl (4R,4'R,5'S)-4-amino-5-(3',4'-dimethyl-2'-oxo-5'-phenyl-1'-imidazolydinyl)-5-oxopentanoate

Downstream raw materials:

pentachlorophenyl ester of D-pyroglutamic acid

ethyl (R)-2-pyrrolidone-5-carboxylate

(R)-N-t-butoxycarbonyl-5-benzyloxymethyl-2-pyrrolidinone

(R)-methyl 1-methyl-5-oxopyrrolidine-2-carboxylate

Refernces

• 1、 Jantos, Katja,Kling, Andreas,Mack, Helmut,Hornberger, Wilfried,Moeller, Achim,Nimmrich, Volker,Lao, Yanbin,Nijsen, Marjoleen. "Discovery of ABT-957: 1-Benzyl-5-oxopyrrolidine-2-carboxamides as selective calpain inhibitors with enhanced metabolic stability". supporting information. p. 1968 - 1973. Retrieved 2019/05/29.
• 2、 Laaksonen, Tiina,Heikkinen, Sami,W?h?l?, Kristiina. "Synthesis of tertiary and quaternary amine derivatives from wood resin as chiral NMR solvating agents". supporting information. p. 20873 - 20886. Retrieved 2015/12/23.