(2S)-5-oxopyrrolidine-2-carboxylic acid

• ChemBase ID: 38765
• Molecular Formular: C5H7NO3
• Molecular Mass: 129.11398
• Monoisotopic Mass: 129.04259309
• SMILES: N1[C@@H](CCC1=O)C(=O)O
• Canonical SMILES: O=C1CC[C@H](N1)C(=O)O
• InChI: InChI=1S/C5H7NO3/c7-4-2-1-3(6-4)5(8)9/h3H,1-2H2,(H,6,7)(H,8,9)/t3-/m0/s1
• InChIKey: ODHCTXKNWHHXJC-VKHMYHEASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-5-oxopyrrolidine-2-carboxylic acid
• IUPAC Systematic name: 5-Oxopyrrolidine-2-carboxylic acid
• IUPAC Traditional name: pyroglutamic acid
• Synonyms: Pidolic acid; 5-Oxo-proline; Pyroglutamic acid; (S)-(-)-2-Pyrrolidone-5-carboxylic acid; (S)-5-Oxo-2-pyrrolidinecarboxylic acid; L-Pyroglutamic acid; L-2-Pyrrolidone-5-carboxylic acid; 5-Oxoproline; L-5-Oxo-2-pyrrolidinecarboxylic acid; L-PYROGLUTAMIC ACID; (S)-(-)-2-Pyrrolidinone-5-carboxylic acid; D-Pyroglutamic Acid; D-Pyrrolidinonecarboxylic Acid; D-Pyrrolidonecarboxylic Acid; (R)-Pyroglutamic Acid; 5-Oxo-D-proline; (R)-(+)-2-Pyrrolidone-5-carboxylic Acid; (R)-2-Pyrrolidone-5-carboxylic Acid; (R)-5-Oxoproline; (R)-2-Pyrrolidinone-5-carboxylic Acid; Pyr-OH; L-Pyroglutamic acid; H-Pyr-OH; 5-Oxo-L-proline; (2S)-5-Oxopyrrolidine-2-carboxylic acid; L-PYROGLUTAMINSAIRE; (S)-5-Oxopyrrolidine-2-carboxylic acid; (S)-(-)-2-吡咯烷酮-5-羧酸; (S)-5-氧-2-吡咯烷羧酸; L-焦谷氨酸; (S)-(-)-2-吡咯烷酮-5-甲酸

Database IDs

• CAS Number: 98-79-3; 4042-36-8
• EC Number: 205-748-3; 202-700-3
• MDL Number: MFCD00005272
• Beilstein Number: 82134; 82132
• Merck Index: 148001
• PubChem SID: 24898722; 161002072; 24898853; 24888086
• PubChem CID: 7405
• CHEBI ID: 16010
• CHEMBL: 284718
• Chemspider ID: 7127
• DrugBank ID: DB03088
• Gmelin ID: 1473408
• KEGG ID: C02237
• MeSH Name: Pyrrolidonecarboxylic+acid
• Unique Ingredient Identifier: SZB83O1W42
• Wikipedia Title: Pyroglutamic_acid

CALCULATED PROPERTIES

• Acid pKa: 3.6133544
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -2.7721438
• LogD (pH = 7.4): -4.2279973
• Log P: -0.8896697
• Molar Refractivity: 28.0878 cm^3
• Polarizability: 11.10192 Å^3
• Polar Surface Area: 66.4 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dimethylformamide; DMSO; H2O: soluble1 M, clear, colorless; Methanol; Water
• Apperance: Off-White Solid
• Melting Point: 138-140°C; 155-160°C; 155-162 °C; 155-163°C; 158-162°C; 160-163 °C(lit.); 184°C
• Partition Coefficient: -0.89
• Optical Rotation: [α]20/D -10.5±1°, c = 5% in H2O; [α]20/D -10°, c = 13 in H2O; -10.5 (c=5 in water)
• Hydrophobicity(logP): -1.147
• pKa: -1.76, 3.48, 12.76
• pKb: 15.76, 10.52, 1.24
• Isoelectric Point: 0.94

Safety Information

• Storage Condition: -20°C Freezer; Room Temperature (15-30°C)
• Storage Warning: Harmful/Irritant/Moisture Sensitive/Store under Argon; IRRITANT
• RTECS: TW3710000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37-60
• TSCA Listed: false; 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥99.0% (T); 95%; 97%; 98%; 98+%
• Optical Purity: enantiomeric ratio: ≥99:1 (GC)
• Ignition Residue: ≤0.05%; ≤0.1%
• Impurities: ≤0.0005% Phosphorus (P)
• Cation Traces: Al: ≤0.0005%; Ca: ≤0.0005%; Cu: ≤0.0005%; Fe: ≤0.0005%; K: ≤0.005%; Mg: ≤0.0005%; Na: ≤0.005%; NH4+: ≤0.05%; Pb: ≤0.001%; Zn: ≤0.0005%
• Antion Traces: chloride (Cl-): ≤0.05%; sulfate (SO42-): ≤0.05%
• Product Line: BioXtra
• Empirical Formula (Hill Notation): C5H7NO3

DETAILS

MP Biomedicals - 05218218

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02102781

Crystalline

Sigma Aldrich - P75202

Packaging
100 g in poly bottle
Application
Building block for asymmetric synthesis1 and pharmaceuticals.2

Sigma Aldrich - 83160

Packaging
25, 100, 500 g in poly bottle

Toronto Research Chemicals - P998500

Serves as a building block in the synthesis of diphthamide.

REFERENCES

• Evans, D.A. and Lundy, K.M.: J. Am. Chem. Soc., 114, 1495 (1992)
• Reduction to the alcohol followed by reaction with benzaldehyde gives a bicyclic lactam which is a useful chiral synthon: J. Org. Chem., 51, 3140 (1986); Tetrahedron Lett., 32, 1379 (1991):
  
• Resolving agent for chiral bases: Helv. Chim. Acta, 41, 181 (1958). Versatile chiral starting material:
• For use in an efficient synthesis of quinolizidine and indolizidine alkaloids, see: J. Org. Chem., 60, 717 (1995).