D-Pyroglutamic acid
- CAS No.
- 4042-36-8
- Chemical Name:
- D-Pyroglutamic acid
- Synonyms
- (R)-5-OXOPYRROLIDINE-2-CARBOXYLIC ACID;5-OXO-D-PROLINE;D-PYR-OH;H-D-PYR-OH;D-pyroglutamate;D-Pyrog;D-PyrogL;223-735-0;D- pGlu-OH;H-D-PGLU-OH
- CBNumber:
- CB0271107
- Molecular Formula:
- C5H7NO3
- Molecular Weight:
- 129.11
- MOL File:
- 4042-36-8.mol
- MSDS File:
- SDS
- Modify Date:
- 2024/7/29 15:17:36
| 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 |
| form | Solid |
| pka | 3.48±0.20(Predicted) |
| color | Off-White to Light Beige |
| optical activity | [α]22/D +10°, c = 1.5 in H2O |
| Water Solubility | soluble |
| Merck | 14,8001 |
| BRN | 82133 |
| InChIKey | ODHCTXKNWHHXJC-GSVOUGTGSA-N |
| CAS DataBase Reference | 4042-36-8(CAS DataBase Reference) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS07 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Warning | |||||||||
| Hazard statements | H315-H319-H335 | |||||||||
| Precautionary statements | P261-P280a-P304+P340-P305+P351+P338-P405-P501a | |||||||||
| Hazard Codes | Xi | |||||||||
| Risk Statements | 36/37/38 | |||||||||
| Safety Statements | 26-36-37/39 | |||||||||
| WGK Germany | 3 | |||||||||
| HS Code | 29339900 | |||||||||
| NFPA 704 |
|
D-Pyroglutamic acid price More Price(6)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich(India) | 422614 | (R)-(+)-2-Pyrrolidone-5-carboxylic acid 95% | 4042-36-8 | 10G | ₹10976.55 | 2022-06-14 | Buy |
| ALFA India | ALF-B24678-22 | (R)-(+)-2-Pyrrolidinone-5-carboxylic acid, 98+% | 4042-36-8 | 100g | ₹60314 | 2022-05-26 | Buy |
| TCI Chemicals (India) | P1354 | D-Pyroglutamic Acid | 4042-36-8 | 5G | ₹4500 | 2022-05-26 | Buy |
| ALFA India | ALF-B24678-14 | (R)-(+)-2-Pyrrolidinone-5-carboxylic acid, 98+% | 4042-36-8 | 25g | ₹6514 | 2022-05-26 | Buy |
| TCI Chemicals (India) | P1354 | D-Pyroglutamic Acid | 4042-36-8 | 25G | ₹8200 | 2022-05-26 | Buy |
D-Pyroglutamic acid Chemical Properties,Uses,Production
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.
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.
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.
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
Preparation Products
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