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5-Oxo-D-prolin

D-Pyroglutamic acid Struktur
4042-36-8
CAS-Nr.
4042-36-8
Bezeichnung:
5-Oxo-D-prolin
Englisch Name:
D-Pyroglutamic acid
Synonyma:
(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
Summenformel:
C5H7NO3
Molgewicht:
129.11
MOL-Datei:
4042-36-8.mol

5-Oxo-D-prolin Eigenschaften

Schmelzpunkt:
155-162 °C
alpha 
27.5 º (c=10,1N NaOH)
Siedepunkt:
239.15°C (rough estimate)
Dichte
1.3816 (rough estimate)
Brechungsindex
10 ° (C=5, H2O)
storage temp. 
Sealed in dry,Room Temperature
L?slichkeit
Dimethylformamide, DMSO (Slightly), Methanol (Slightly), Water
Aggregatzustand
Solid
pka
3.48±0.20(Predicted)
Farbe
Off-White to Light Beige
Optische Aktivit?t
[α]22/D +10°, c = 1.5 in H2O
Wasserl?slichkeit
soluble
Merck 
14,8001
BRN 
82133
InChIKey
ODHCTXKNWHHXJC-GSVOUGTGSA-N
CAS Datenbank
4042-36-8(CAS DataBase Reference)
Sicherheit
  • Risiko- und Sicherheitserkl?rung
  • Gefahreninformationscode (GHS)
Kennzeichnung gef?hrlicher Xi
R-S?tze: 36/37/38
S-S?tze: 26-36-37/39
WGK Germany  3
HS Code  29339900
Bildanzeige (GHS) GHS hazard pictograms
Alarmwort Warnung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H315 Verursacht Hautreizungen. Hautreizung Kategorie 2 Warnung GHS hazard pictogramssrc="/GHS07.jpg" width="20" height="20" /> P264, P280, P302+P352, P321,P332+P313, P362
H319 Verursacht schwere Augenreizung. Schwere Augenreizung Kategorie 2 Warnung GHS hazard pictogramssrc="/GHS07.jpg" width="20" height="20" /> P264, P280, P305+P351+P338,P337+P313P
H335 Kann die Atemwege reizen. Spezifische Zielorgan-Toxizit?t (einmalige Exposition) Kategorie 3 (Atemwegsreizung) Warnung GHS hazard pictogramssrc="/GHS07.jpg" width="20" height="20" />
Sicherheit
P261 Einatmen von Staub vermeiden.
P304+P340 BEI EINATMEN: Die Person an die frische Luft bringen und für ungehinderte Atmung sorgen.
P305+P351+P338 BEI KONTAKT MIT DEN AUGEN: Einige Minuten lang behutsam mit Wasser spülen. Eventuell vorhandene Kontaktlinsen nach M?glichkeit entfernen. Weiter spülen.
P405 Unter Verschluss aufbewahren.

5-Oxo-D-prolin Chemische Eigenschaften,Einsatz,Produktion Methoden

R-S?tze Betriebsanweisung:

R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.

S-S?tze Betriebsanweisung:

S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.

Beschreibung

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.

Chemische Eigenschaften

white to light yellow crystal powder.

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.

Biologische Aktivit?t

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.

l?uterung methode

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.]

Einzelnachweise

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

5-Oxo-D-prolin Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


5-Oxo-D-prolin Anbieter Lieferant Produzent Hersteller Vertrieb H?ndler.

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4042-36-8(5-Oxo-D-prolin)Verwandte Suche:


  • (R)-5-PYRROLIDONE-2-CARBOXYLIC ACID
  • (R)-(+)-5-OXO-2-PYRROLIDINECARBOXYLIC ACID
  • (R)-5-OXO-2-PYRROLIDINECARBOXYLIC 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
  • 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-PROLINE, 5-OXO-
  • 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
  • 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)
  • (2R)-5-oxo-2-pyrrolidinecarboxylate
  • D-Pyroglutamic Aicd
  • D-PyroglutamicAcid>
  • D-Pyrog
  • D-PyrogL
  • D-Pyroglutamic acid USP/EP/BP
  • (R)-5-OXOPYRROLIDINE-2-CARBOXYLIC ACID
  • 5-OXO-D-PROLINE
  • D-PYR-OH
  • H-D-PYR-OH
  • 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
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