Introduction：Basic information about D-Pyroglutamic acid CAS 4042-36-8, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
D-Pyroglutamic acid Basic information
| Product Name: | D-Pyroglutamic acid |
| Synonyms: | (R)-5-PYRROLIDONE-2-CARBOXYLIC ACID;(R)-(+)-5-OXO-2-PYRROLIDINECARBOXYLIC ACID;(R)-5-OXO-2-PYRROLIDINECARBOXYLIC ACID;(R)-5-OXOPYRROLIDINE-2-CARBOXYLIC ACID;(R)-(+)-2-PYRROLIDINONE-5-CARBOXYLIC ACID;(R)-2-PYRROLIDINONE-5-CARBOXYLIC ACID;(R)-(+)-2-PYRROLIDONE-5-CARBOXYLIC ACID;(R)-2-PYRROLIDONE-5-CARBOXYLIC ACID |
| CAS: | 4042-36-8 |
| MF: | C5H7NO3 |
| MW: | 129.11 |
| EINECS: | 223-735-0 |
| Product Categories: | Amino Acids & Derivatives;Chiral Reagents;amino acid;Pyroglutamic acid [Pyr, pGu];Amino Acids 13C, 2H, 15N;Amino Acids;Biochemistry;Biological-modified Amino Acids;for Resolution of Bases;Optical Resolution;Synthetic Organic Chemistry;Heterocycles;Amino Acids and Derivatives;chiral;pharmacetical;bc0001 |
| Mol File: | 4042-36-8.mol |
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D-Pyroglutamic acid Chemical Properties
| Melting point | 155-162 °C |
| alpha | 27.5 º (c=10,1N NaOH) |
| Boiling point | 239.15°C (rough estimate) |
| density | 1.3816 (rough estimate) |
| refractive index | 10 ° (C=5, H2O) |
| storage temp. | Sealed in dry,Room Temperature |
| solubility | Dimethylformamide, DMSO (Slightly), Methanol (Slightly), Water |
| pka | 3.48±0.20(Predicted) |
| form | Solid |
| color | Off-White to Light Beige |
| Optical Rotation | [α]22/D +10°, c = 1.5 in H2O |
| Water Solubility | soluble |
| Merck | 14,8001 |
| BRN | 82133 |
| Major Application | peptide synthesis |
| InChI | 1S/C5H7NO3/c7-4-2-1-3(6-4)5(8)9/h3H,1-2H2,(H,6,7)(H,8,9)/t3-/m1/s1 |
| InChIKey | ODHCTXKNWHHXJC-GSVOUGTGSA-N |
| SMILES | OC(=O)[C@H]1CCC(=O)N1 |
| CAS DataBase Reference | 4042-36-8(CAS DataBase Reference) |
Safety Information
| Hazard Codes | Xi |
| Risk Statements | 36/37/38 |
| Safety Statements | 26-36-37/39 |
| WGK Germany | 3 |
| HS Code | 29339900 |
| Storage Class | 11 - Combustible Solids |
D-Pyroglutamic acid Usage And Synthesis
| Description | D-Pyroglutamic acid, also known as 5-oxo-D-proline, is a metabolite of D-glutamate. It is formed from D-glutamate by D-glutamate cyclase. The levels of D-pyroglutamic acid are increased in the urine of patients with nascent metabolic syndrome and the plasma of patients with end-stage renal disease. |
| Chemical Properties | white to light yellow crystal powder. |
| Occurrence | D-pyroglutamic acid is formed by the dehydration between the α-NH2 group and the γ-hydroxyl group of glutamic acid to form an intramolecular amide bond; it can also be formed by the loss of an amide group in the glutamine molecule. |
| Uses | Serves as a building block in the synthesis of diphthamide. |
| Definition | ChEBI: D-Pyroglutamic acid is the D-enantiomer of 5-oxoproline. It has a role as a metabolite. It is a D-proline derivative and a 5-oxoproline. It is a conjugate acid of a 5-oxo-D-prolinate. It is an enantiomer of a 5-oxo-L-proline. |
| reaction suitability | reaction type: solution phase peptide synthesis |
| Biological Activity | D-Pyroglutamic acid (PCA) is a cyclic derivative of glutamic acid, physiologically present in mammalian tissues. It has been shown that PCA releases GABA from the cerebral cortex and displays anti-anxiety effects in a simple approach-avoidance conflict situation in the rat. In clinical pharmacology experiments, PCA significantly shortens the plasma half-life of ethanol during acute intoxication. |
| Synthesis | D-Pyroglutamic acid is 5-oxoproline. It is formed by the dehydration of the ??-NH2 group of glutamic acid and the ??-hydroxyl group to form an intramolecular amide bond; it can also be formed by the loss of the amide group in the glutamine molecule. |
| Purification Methods | Purify R-pyroglutamic acid by dissolving it in H2O, filtering, passing the filtrate through Dowex 50 (H+ form), washing with H2O, pooling washings, evaporating, removing H2O azeotropically with Me2CO and *C6H6, washing the residue with Et2O and recrystallising from EtOH/pet ether. [Pradeller et al. Collect Czech Chem Commun 42 79, 80 1977, Beilstein 22/6 V 7.] |
| References | 1. Ariyoshi, M., Katane, M., Hamase, K., et al. D-Glutamate is metabolized in the heart mitochondria. Sci. Rep. 7, 43911 (2017). DOI:10.1038/srep43911
2. Shim, K., Gulhar, R., and Jialal, I. Exploratory metabolomics of nascent metabolic syndrome. J. Diabetes Complications 33(3), 212-216 (2019). DOI:10.1016/j.jdiacomp.2018.12.002
3. Palekar AG, et al. Accumulation of 50oxo-L-proline and 5-oxo-D-proline in the blood plasma in end stage renal disease. Biochem Med. 1975 Nov;14(3):339-45. DOI:10.1016/0006-2944(75)90052-6
4. D-Pyroglutamic Acid Production from L-Glutamic Acid by Successive Racemization, Resolution and Dehydration. DOI:10.6967/JCICE.200003.0177 |
D-Pyroglutamic acid Preparation Products And Raw materials
| Raw materials | 5-Hydroxymethylpyrrolidin-2-one-->L-Pyroglutamic acid-->D(-)-Glutamic acid-->(-)-D-PYROGLUTAMIC ACID METHYL ESTER |
| Preparation Products | L-Pyroglutamic acid-->Ethanol-->(R)-(-)-1-(2-Pyrrolidinylmethyl)pyrrolidine-->Fasoracetam-->D-PYROGLUTAMIC ACID TERT-BUTYL ESTER-->(+)-D-PYROGLUTAMOL P-TOLUENESULFONATE-->3-(tert-butylamino)propane-1,2-diol |
