(±)-2-pyrrolidone-5-carboxylic acid

DL-proline, 5-oxo-

CAS: 149-87-1 C5 H7 N O3 MW: 129.11539000

Identification

Name(±)-2-pyrrolidone-5-carboxylic acid
IUPAC5-oxopyrrolidine-2-carboxylic acid
CAS Number149-87-1
EINECS205-748-3
FDA UNII6VT1YZM21H
Molecular FormulaC5 H7 N O3
Molecular Weight129.11539000
MDL NumberMFCD00064322
Nikkaji NumberJ36.868G
Beilstein082131

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 SDSView
Oral/Parenteral ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorycosmetic agents
Recommendation for (±)-2-pyrrolidone-5-carboxylic acid usage levels up tonot for fragrance use.
Recommendation for (±)-2-pyrrolidone-5-carboxylic acid flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

not found in nature

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.