(±)-2-pyrrolidone-5-carboxylic acid
DL-proline, 5-oxo-
Identification
| Name | (±)-2-pyrrolidone-5-carboxylic acid |
| IUPAC | 5-oxopyrrolidine-2-carboxylic acid |
| CAS Number | 149-87-1 |
| EINECS | 205-748-3 |
| FDA UNII | 6VT1YZM21H |
| Molecular Formula | C5 H7 N O3 |
| Molecular Weight | 129.11539000 |
| MDL Number | MFCD00064322 |
| Nikkaji Number | J36.868G |
| Beilstein | 082131 |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 453.00 to 454.00 °C. @ 760.00 mm Hg (est) |
| Flash Point | 442.00 °F. TCC ( 227.80 °C. ) (est) |
| logP (o/w) | -1.348 (est) |
| Soluble in | water, 3.799e+005 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | cosmetic agents |
| Recommendation for (±)-2-pyrrolidone-5-carboxylic acid usage levels up to | not for fragrance use. |
| Recommendation for (±)-2-pyrrolidone-5-carboxylic acid flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
5-
carboxy-2-pyrrolidinone
5-oxo-dextro,laevo-
proline
5-oxo-DL-
proline
proline, 5-oxo-
DL-
proline, 5-oxo-
dextro,laevo-
pyroglutamic acid
DL-
pyroglutamic acid
5-oxo
pyrrolidine-2-carboxylic acid
5-oxo-
pyrrolidine-2-carboxylic acid
2-oxo
pyrrolidine-5-carboxylic acid
5-oxo-2-
pyrrolidinecarboxylic acid
DL-5-oxo-2-
pyrrolidinecarboxylic acid
PubMed:
The skin microbiome of caspase-14-deficient mice shows mild dysbiosis.
PubMed:
Nanomolar detection of hypochlorite by a rhodamine-based chiral hydrazide in absolute aqueous media: application in tap water analysis with live-cell imaging.
PubMed:
Novel intercluster compound between a heptakis{triphenylphosphinegold(I)}dioxonium cation and an α-Keggin polyoxometalate anion.
PubMed:
Chiral sensing using an achiral europium(III) complex by induced circularly polarized luminescence.
PubMed:
Preparation and chiro-optical characterization of polyaniline doped with (+) or (-)-2-pyrrolidone-5-carboxylic acid (PCA).
PubMed:
Intercluster compound between a tetrakis{triphenylphosphinegold(I)}oxonium cation and a keggin polyoxometalate (POM): formation during the course of carboxylate elimination of a monomeric triphenylphosphinegold(I) carboxylate in the presence of POMs.
PubMed:
Natural moisturizing factor components in the stratum corneum as biomarkers of filaggrin genotype: evaluation of minimally invasive methods.
PubMed:
Characterization of low-molecular-weight antiyeast metabolites produced by a food-protective Lactobacillus-Propionibacterium coculture.
PubMed:
New AZT conjugates as potent anti-HIV agents.
PubMed:
Qualitative and quantitative analysis of new amino acid derivatives of anticonvulsant activity.
PubMed:
Synthesis and characterization of water-soluble silver(I) complexes with L-histidine (H2his) and (S)-(-)-2-pyrrolidone-5-carboxylic acid (H2pyrrld) showing a wide spectrum of effective antibacterial and antifungal activities. Crystal structures of chiral helical polymers [Ag(Hhis)]n and ([Ag(Hpyrrld)]2)n in the solid state.
PubMed:
Functional and chemical characterization of Hymenoptaecin, an antibacterial polypeptide that is infection-inducible in the honeybee (Apis mellifera).
PubMed:
Pyrrolidone carboxylic acid in acute and chronic alcoholism. Preclinical and clinical studies.
PubMed:
Over-estimation of glucose-6-phosphatase activity in brain in vivo. Apparent difference in rates of [2-3H]glucose and [U-14C]glucose utilization is due to contamination of precursor pool with 14C-labeled products and incomplete recovery of 14C-labeled metabolites.
PubMed:
The lactam of alpha-guanidinoglutaric acid (1-amidino-2-pyrrolidone-5-carboxylic acid).
PubMed:
Studies on the accumulation of L-pyroglutamic acid in guinea pig epidermis.
PubMed:
The crystal structure of 3-hydroxy-3-isobutyl-2-pyrrolidone-5-carboxylic acid, lactam of 4-hydroxy-4-isobutylglutamic acid from Reseda odorata L.
PubMed:
The influence of glutamine, its decomposition products, and glutaminase on the transformation of human and mouse lymphocytes.
PubMed:
Specificity of gamma-glutamyl cyclotransferase.
PubMed:
The concentration of pyroglutamic acid (2-pyrrolidone-5-carboxylic acid) in normal and psoriatic epidermis, determined on a microgram scale by gas chromatography.
PubMed:
Inhibition of 5-oxoprolinase by 2-imidazolidone-4-carboxylic acid.
PubMed:
Enzymatic formation of L- & D-2-pyrrolidone 5-carboxylic acid from L- & D-glutamic acid in human skin & albino rat epidermis.
PubMed:
Enzymatic conversion of 5-oxo-L-proline (L-pyrrolidone carboxylate) to L-glutamate coupled with cleavage of adenosine triphosphate to adenosine diphosphate, a reaction in the -glutamyl cycle.