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

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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)

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Safety

Hazard Codes: Xi
Risk Statements: 36/37/38
Safety Statements: 26-36-37/39
WGK Germany: 3
HS Code: 29339900

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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.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 422614
Product name: (R)-(+)-2-Pyrrolidone-5-carboxylic acid
Purity: 95%
Packaging: 10g
Price: $146
Updated: 2023/06/20

TCI Chemical

Product number: P1354
Product name: D-Pyroglutamic Acid
Purity: >98.0%(T)
Packaging: 5g
Price: $68
Updated: 2024/03/01

TCI Chemical

Product number: P1354
Product name: D-Pyroglutamic Acid
Purity: >98.0%(T)
Packaging: 25g
Price: $167
Updated: 2024/03/01

Alfa Aesar

Product number: B24678
Product name: (R)-(+)-2-Pyrrolidinone-5-carboxylic acid, 98+%
Packaging: 5g
Price: $63.65
Updated: 2024/03/01

Alfa Aesar

Product number: B24678
Product name: (R)-(+)-2-Pyrrolidinone-5-carboxylic acid, 98+%
Packaging: 25g
Price: $203.65
Updated: 2024/03/01

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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.

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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D-Pyroglutamic acid Suppliers

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View Lastest Price from D-Pyroglutamic acid manufacturers

Sichuan HongRi Pharma-Tech Co.,Ltd

Product: D-Pyr 4042-36-8
Price: US $0.00-0.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 1T+
Release date: 2023-09-13

HEBEI SHENGSUAN CHEMICAL INDUSTRY CO.,LTD

Product: D-Pyroglutamic acid 4042-36-8
Price: US $999.00-800.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 5000
Release date: 2024-08-22

WUHAN FORTUNA CHEMICAL CO., LTD

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

4042-36-8, D-Pyroglutamic acidRelated Search:

D-Proline 2-Pyrrolidinone Polyglutamic acid GLDH L-Proline Folic acid Stearic acid Citric acid Ethyl 2-(Chlorosulfonyl)acetate EPA L-Glutamic acid Ascoric Acid Sodium L-pyroglutamate (-)-L-PYROGLUTAMIC ACID,PYROGLUTAMIC ACID,L-PYROGLUTAMIC ACID DL-Pyroglutamic acid (R)-N-BOC-5-METHOXYCARBONYL-2-PYRROLIDINONE Ethyl D-(-)-pyroglutamate Z-L-PYROGLUTAMIC ACID,N-ALPHA-CARBOBENZOXY-L-PYROGLUTAMIC ACID,N-ALPHA-CBZ-L-PYROGLUTAMIC ACID,N-BENZYLOXYCARBONYL-L-PYROGLUTAMIC ACID,N-CBZ-L-PYROGLUTAMIC ACID

(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

5-OXO-D-PROLIN

5-OXO-D-PROLINE

2-PYRROLIDINONE-(R)-5-CARBOXYLIC ACID

D-GLUTAMIC ACID LACTAM

D-5-OXO-2-PYRROLIDINECARBOXYLIC ACID

d-5-pyrrolidone-2-carboxylic acid

(+)-D-PYROGLUTAMIC ACID

D-PYROGLUTAMIC ACID

D-PYR-OH

D-PROLINE, 5-OXO-

H-D-PYR-OH

H-D-PGLU-OH

(2R)-5-Oxopyrrolidin-2-ylcarboxylic acid

R-2-PYRROLIDONE-5-CARBOXYLIC ACID 97%

D-Pyroglutamicacid=H-D-Pyr-OH=D-2-Pyrrolidone-5-carboxylicacid

D-2-PYRROLIDONE-5-CARBOXYLIC ACID

D-5-Oxoproline

(R)-(+)-2-Pyrrolidone-5-carboxylic acid, 98+%

D-Pyroglutamic

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

D- pGlu-OH

(R)-(+)-2-PYRROLIDINONE-5-CARBOXYLIC ACID, 98+%

D-Pyrroglutamic acid

D-Pyroglutamic acid, (R)-2-Pyrrolidone-5-carboxylic acid, (R)-5-Oxo-2-pyrrolidinecarboxylic acid

(2R)-5-oxo-2-pyrrolidinecarboxylate

D-5-Oxo-2-pyrrolidinecarboxylic acid, D-Pyroglutamic acid

(R)-2-Pyrrolidone-5-carboxylic acid, (R)-5-Oxo-2-pyrrolidinecarboxylic acid

D-Pyroglutamic acid ,98%

(R)-5-Oxoproline

(R)-PyroglutaMic Acid

D-Pyrrolidinonecarboxylic Acid

D-Pyrrolidonecarboxylic Acid

D-Glutamic Acid Lactam (R)-5-Oxopyrrolidine-2-carboxylic Acid (R)-5-Pyrrolidone-2-carboxylic Acid

223-735-0

D-Pyr-OH≥ 99% (assay)

D-Pyroglutamic Aicd

D-PyroglutamicAcid&gt

D-Pyrog

D-PyrogL

D-Pyroglutamic acid USP/EP/BP

D-pyroglutamate

RSYY（Cyclobenzaprine hydrochloride)-6

(+)-Pyroglutamic acid

D-Pyroglutamic Acid,95%

Pyroglutamic acid, D-

4042-36-8

C5H7NO3

Optical Resolution

for Resolution of Bases

Peptide Synthesis