5-Oxopyrrolidine-2-carboxylic acid

Names

[ CAS No. ]:
149-87-1

[ Name ]:
5-Oxopyrrolidine-2-carboxylic acid

[Synonym ]:
MFCD00064322
L-Pidolic acid
H-DL-Pyr-OH
DL-2-Pyrrolidone-5-carboxylic acid
(S)-(-)-2-pyrrolidone-5-carboxylic acid
Ajidew A 100
Pyrrolidonecarboxylic acid
(S)-(-)-γ-Butyrolactam-γ-carboxylic acid
PyroGlu
L-Proline, 5-oxo-
5-Oxopyrrolidine-2-carboxylic Acid
Pyroglutamic acid
2H-Pyrrole-2-carboxylic acid, 3,4-dihydro-5-hydroxy-, (2S)-
L-5-Oxoproline
DL-Pyroglutamic acid
(S)-(−)-Pyroglutamic acid
a-Aminoglutaric Acid Lactam
5-oxo-proline
(S)-(−)-2-Pyrrolidone-5-carboxylic acid
(-)-Pyroglutamic acid
L-Glutamic Acid g-Lactam
5-Oxo-L-proline
5-Pyrrolidinone-2-carboxylic acid
D,l-2-Pyrrolidone-5-Carboxylic Acid
Proline, 5-oxo-, L-
PCA
Glutamic Acid Lactam
2-L-Pyrrolidone-5-carboxylic acid
pidolic acid
EINECS 205-748-3
(2S)-5-Hydroxy-3,4-dihydro-2H-pyrrole-2-carboxylic acid
DL-Glutamic Acid Lactam
5-L-oxoproline
2-Pyrrolidone-5-carboxylic acid
(S)-(-)-g-Butyrolactam-g-carboxylic Acid

Biological Activity

[Description]:

DL-Pyroglutamic acid (CAE) as an inactivator of hepatitis B surface, inactivates vaccinia virus, herpes simplex virus, and influenza virus except poliovirus. DL-Pyroglutamic acid is also a possible inhibitor of GABA transaminase, increases GABA amount with antiepileptic action[1][2].

[Related Catalog]:

Signaling Pathways >> Anti-infection >> Influenza Virus

Research Areas >> Infection

Signaling Pathways >> Membrane Transporter/Ion Channel >> GABA Receptor

Signaling Pathways >> Neuronal Signaling >> GABA Receptor

[In Vitro]

DL-Pyroglutamic acid results 50 and 100% inactivation of the antigen of 0.01-0.025% and 0.025-0.05%, respectively[1]. DL-Pyroglutamic acid is a possible glutamate antagonist, blocks glutamate miniature-end-plate potential in locust muscle-Druce and Bradford[2].

[In Vivo]

DL-Pyroglutamic acid (0.775 mM/L) completely abolishes the myoclonic jerks and EEG spikes in rats model of epileptic by cobalt implantation in the sensorimotor cerebral cortex[2].

[References]

[1]. Sugimoto Y, et al. N-alpha-Cocoyl-L-arginine ethyl ester, DL-pyroglutamic acid salt, as an inactivator of hepatitis B surface antigen. Antimicrob Agents Chemother. 1979 Sep;16(3):329-32.

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
453.1±38.0 °C at 760 mmHg

[ Melting Point ]:
180-185ºC

[ Molecular Formula ]:
C₅H₇NO₃

[ Molecular Weight ]:
129.114

[ Flash Point ]:
227.8±26.8 °C

[ Exact Mass ]:
129.042587

[ PSA ]:
66.40000

[ LogP ]:
-2.39

[ Vapour Pressure ]:
0.0±2.4 mmHg at 25°C

[ Index of Refraction ]:
1.512

[ Water Solubility ]:
5.67 g/100 mL (20 ºC)

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi:Irritant;

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S26-S37/39

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ HS Code ]:
29337900

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933790090

[ Summary ]:
2933790090. other lactams. VAT:17.0%. Tax rebate rate:9.0%. . MFN tariff:9.0%. General tariff:20.0%

Articles

Comparison of capillary electrophoresis-mass spectrometry and hydrophilic interaction chromatography-mass spectrometry for anionic metabolic profiling of urine.

Talanta 132 , 1-7, (2014)

In order to assess the utility of a recently developed capillary electrophoresis-mass spectrometry (CE-MS) method for the study of anionic metabolites in urine, a comparison was made with hydrophilic ...