ChemicalBook > CAS DataBase List > D-Pyroglutamic acid

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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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