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

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 Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

HS Code 

29339900

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

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.

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(4042-36-8)Related Product Information

• 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