D-Pyroglutamic acid
- Product Name
- 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
- Formula Weight
- 129.11
- MOL File
- 4042-36-8.mol
D-Pyroglutamic acid Property
- 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
- Hazard Codes
- Xi
- Risk Statements
- 36/37/38
- Safety Statements
- 26-36-37/39
- WGK Germany
- 3
- HS Code
- 29339900
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P405Store locked up.
N-Bromosuccinimide Price
- Product number
- 422614
- Product name
- (R)-(+)-2-Pyrrolidone-5-carboxylic acid
- Purity
- 95%
- Packaging
- 10g
- Price
- $146
- Updated
- 2023/06/20
- Product number
- P1354
- Product name
- D-Pyroglutamic Acid
- Purity
- >98.0%(T)
- Packaging
- 5g
- Price
- $68
- Updated
- 2025/07/31
- Product number
- P1354
- Product name
- D-Pyroglutamic Acid
- Purity
- >98.0%(T)
- Packaging
- 25g
- Price
- $167
- Updated
- 2025/07/31
- Product number
- P998500
- Product name
- (R)-2-Pyrrolidinone-5-carboxylicAcid
- Packaging
- 25g
- Price
- $120
- Updated
- 2021/12/16
- Product number
- JK133217
- Product name
- D-Pyroglutamic Acid
- Purity
- 98%
- Packaging
- 10g
- Price
- $123
- Updated
- 2021/12/16
D-Pyroglutamic acid Chemical Properties,Usage,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.
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.
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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View Lastest Price from D-Pyroglutamic acid manufacturers
- Product
- D-Pyroglutamic acid 4042-36-8
- Price
- US $0.00-0.00/G
- Min. Order
- 1G
- Purity
- 99%
- Supply Ability
- 200000t
- Release date
- 2025-06-06
- Product
- D-Pyroglutamic acid 4042-36-8
- Price
- US $0.00-0.00/Kg/Drum
- Min. Order
- 1KG
- Purity
- 98%-101%
- Supply Ability
- 1000KG
- Release date
- 2021-06-08
- Product
- D-Pyroglutamic acid 4042-36-8
- Price
- US $7.00/kg
- Min. Order
- 1kg
- Purity
- 0.99
- Supply Ability
- 10000
- Release date
- 2024-09-05