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Sigma-Aldrich

2-Pyrrolidone-5-carboxylic acid

99%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C5H7NO3
CAS Number:
149-87-1
Molecular Weight:
129.11
Beilstein:
82134
EC Number:
205-748-3
MDL number:
MFCD00064322
UNSPSC Code:
12352106
PubChem Substance ID:
24857617
NACRES:
NA.22

Quality Level

200

Assay

99%

reaction suitability

reaction type: solution phase peptide synthesis

mp

183-185 °C (lit.)

application(s)

peptide synthesis

SMILES string

OC(=O)C1CCC(=O)N1

InChI

1S/C5H7NO3/c7-4-2-1-3(6-4)5(8)9/h3H,1-2H2,(H,6,7)(H,8,9)

InChI key

ODHCTXKNWHHXJC-UHFFFAOYSA-N

General description

DL-Pyroglutamic acid serves as a chiral building block and a chiral auxiliary in asymmetric synthesis.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Pyroglutamic acid: a versatile building block in asymmetric synthesis
C Najera, et al.
Tetrahedron Asymmetry, 10, 2245-2303 (1999)
Stefania Perticaroli et al.
Biochimica et biophysica acta. Biomembranes, 1861(2), 403-409 (2018-11-23)
The superficial layer of the skin, the stratum corneum (SC), consists of corneocytes surrounded by lipid regions and acts as a protective barrier for the body against water loss, toxic agents and microorganisms. As most substances permeate the stratum corneum
Andres Gil et al.
Journal of pharmaceutical and biomedical analysis, 160, 289-296 (2018-08-17)
Oxidative stress is suggested to play an important role in several pathophysiological conditions. A recent study showed that decreasing 5-oxoproline (pyroglutamate) concentration, an important mediator of oxidative stress, by over-expressing 5-oxoprolinase, improves cardiac function post-myocardial infarction in mice. The aim
Tetsuyuki Takahashi et al.
Biochemical and biophysical research communications, 516(2), 388-396 (2019-06-21)
Inhibition of prostaglandin E2 signaling via EP2/EP4 prostanoid receptors suppresses Insulin-like growth factor (IGF)-1-induced proliferation of pancreatic cancer BxPC-3 cells. To better understand the mechanism of EP2/EP4 signaling for controlling cell proliferation, we performed metabolome analyses in BxPC-3 cells treated with IGF-1
Lucia Montenegro et al.
Nanomaterials (Basel, Switzerland), 9(1) (2019-01-02)
Idebenone (IDE), a strong antioxidant widely investigated for the treatment of neurodegenerative diseases and skin disorders, shows low oral and topical bioavailability due to its unfavorable physico-chemical properties. In this work, to improve IDE topical effectiveness, we explored a two-steps
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