(±)-2-pyrrolidone-5-carboxylic acid
DL-proline, 5-oxo-
 
Notes:
2-Pyrrolidone-5-carboxylic 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. [HMDB]
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      149-87-1 2-Pyrrolidone-5-carboxylic acid 95%
       
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      16-91402 DL-PYROGLUTAMIC ACID
       
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      G0061 DL-Pyroglutamic Acid >99.0%(T)
       
Synonyms   Articles   Notes   Search
CAS Number: 149-87-1Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg: 205-748-3
FDA UNII: 6VT1YZM21H
Nikkaji Web: J36.868G
Beilstein Number: 082131
MDL: MFCD00064322
XlogP3-AA: -0.80 (est)
Molecular Weight: 129.11539000
Formula: C5 H7 N O3
BioActivity Summary: listing
NMR Predictor: Predict (works with chrome or firefox)
Category: cosmetic agents
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar: Search
Google Books: Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Google Patents: Search
US Patents: Search
EU Patents: Search
Pubchem Patents: Search
PubMed: Search
NCBI: Search
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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)
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
Cosmetic Uses:
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Suppliers:
BOC Sciences
For experimental / research use only.
2-Pyrrolidone-5-carboxylic acid 95%
EMD Millipore
For experimental / research use only.
DL-2-Pyrrolidone-5-carboxylic acid
Penta International
DL-PYROGLUTAMIC ACID
Santa Cruz Biotechnology
For experimental / research use only.
2-Pyrrolidone-5-carboxylic Acid
Sigma-Aldrich: Aldrich
For experimental / research use only.
(±)-2-Pyrrolidone-5-carboxylic Acid 99%
TCI AMERICA
For experimental / research use only.
DL-Pyroglutamic Acid >99.0%(T)
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Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
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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Safety References:
EPI System: View
AIDS Citations: Search
Cancer Citations: Search
Toxicology Citations: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 499
National Institute of Allergy and Infectious Diseases: Data
WGK Germany: 3
 5-oxopyrrolidine-2-carboxylic acid
Chemidplus: 0000149871
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References:
 5-oxopyrrolidine-2-carboxylic acid
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 499
Pubchem (sid): 135025459
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Other Information:
(IUPAC): Atomic Weights of the Elements 2011 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
CHEBI: View
CHEMBL: View
Golm Metabolome Database: Search
KEGG (GenomeNet): C02237
HMDB (The Human Metabolome Database): HMDB00805
FooDB: FDB022254
Export Tariff Code: 2933.79.8500
ChemSpider: View
Wikipedia: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 not found in nature
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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-oxopyrrolidine-2-carboxylic acid
5-oxo-pyrrolidine-2-carboxylic acid
2-oxopyrrolidine-5-carboxylic acid
5-oxo-2-pyrrolidinecarboxylic acid
DL-5-oxo-2-pyrrolidinecarboxylic acid
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Articles:
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.
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