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laevo-pyroglutamic acid

special dietary and nutritional additives
2D:
3D:
CAS Number: 98-79-3
ECHA EC Number: 202-700-3
FDA UNII: SZB83O1W42
Category: special dietary and nutritional additives
IUPAC Name: laevo-pyroglutamic acid
InChI : InChI=1/C5H7NO3/c7-4-2-1-3(6-4)5(8)9/h3H,1-2H2,(H,6,7)(H,8,9)/t3-/m0/s1
Std.InChI: InChI=1S/C5H7NO3/c7-4-2-1-3(6-4)5(8)9/h3H,1-2H2,(H,6,7)(H,8,9)/t3-/m0/s1
InChIKey : ODHCTXKNWHHXJC-VKHMYHEABY
Std.InChIKey: ODHCTXKNWHHXJC-VKHMYHEASA-N
SMILES : C1CC(=O)N[C@@H]1C(=O)O
MDL: MFCD00005272

US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:

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Pubchem Patents:Search
PubMed:Search
NCBI:Search

Physical Properties:

Appearance:white crystalline powder (est)
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 184.00 to 185.00 °C. @ 760.00 mm Hg
Boiling Point: 453.13 °C. @ 760.00 mm Hg (est)
Flash Point: 440.00 °F. TCC ( 226.67 °C. )
logP (o/w): -1.348 (est)
Soluble in:
water, 476000 mg/L @ 13C (exp)

Cosmetic Information:

CosIng:cosmetic data
Cosmetic Uses: humectants
moisturising agents

Suppliers:

Alfa Biotechnology
For experimental / research use only.
L-Pyroglutamic acid 98%
Anhui Haibei
laevo-pyroGlutamic Acid
BOC Sciences
For experimental / research use only.
L-Pyroglutamic acid HPLC>95%
EMD Millipore
For experimental / research use only.
(S)-(-)-2-Pyrrolidone-5-carboxylic acid
Glentham Life Sciences
L-pyroGlutamic Acid
Minasolve
L-pyroGlutamic Acid & Derivatives
Penta International
L-PYROGLUTAMIC ACID
Santa Cruz Biotechnology
For experimental / research use only.
L-pyroGlutamic Acid ≥99%
Sigma-Aldrich: Aldrich
For experimental / research use only.
L-pyroGlutamic Acid ≥99.0% (T)
Solabia
L-Pidolic Acid
Odor: characteristic
Use: APC is also a remarkable vehicle for numerous molecules which must be carried through the body, this is why it is used as a synthesis intermediate. Consequently, SOLABIA Pharma offers highly bioavailable mineral salts such as Magnesium Pidolate.
United International
L-Pyroglutamic acid

Safety Information:

Preferred SDS: View
European information :
Most important hazard(s):
Xi - Irritant
R 36/38 - Irritating to skin and eyes.
S 02 - Keep out of the reach of children.
S 24/25 - Avoid contact with skin and eyes.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 36 - Wear suitable protective clothing.
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:
oral-rat LD50 > 1000 mg/kg
United States Patent Document. Vol. #4882359

Dermal Toxicity:
subcutaneous-rat LD50 > 2000 mg/kg
United States Patent Document. Vol. #4882359

Inhalation Toxicity:
Not determined

Safety in Use Information:

Category:
special dietary and nutritional additives
Recommendation for laevo-pyroglutamic acid usage levels up to:
not for fragrance use.
Recommendation for laevo-pyroglutamic acid flavor usage levels up to:
not for flavor use.

Safety References:

European Food Safety Authority (EFSA) reference(s):

Opinion of the Scientific Panel on food additives, flavourings, processing aids and materials in contact with food (AFC) related to Calcium, iron, magnesium, potassium and zinc L-pidolate as sources for calcium, iron, magnesium, potassium and zinc added for nutritional purposes to food supplements and to foods intended for particular nutritional uses
View page or View pdf

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):98-79-3
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :7405
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
(2S)-5-oxopyrrolidine-2-carboxylic acid
Chemidplus:0000098793
RTECS:TW3710000 for cas# 98-79-3

References:

(2S)-5-oxopyrrolidine-2-carboxylic acid
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:98-79-3
Pubchem (cid):7405
Pubchem (sid):134971460

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):C01879
HMDB (The Human Metabolome Database):HMDB00267
FooDB:FDB014506
YMDB (Yeast Metabolome Database):YMDB00107
Export Tariff Code:2933.79.5000
FDA Listing of Food Additive Status:View
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View

Potential Blenders and core components :

None Found

Potential Uses:

humectants
moisturising agents

Occurrence (nature, food, other):

molasses
Search PMC Picture
soybean seed
Search Trop Picture

Synonyms:

(S)-(-)-g-butyrolactam-g-carboxylate
(S)-(-)-g-butyrolactam-g-carboxylic Acid
L-pyroglutamic acid
L-glutamic acid g-lactam
L-glutamic acid gamma-lactam
laevo-glutamic acid gamma-lactam
PCA
pidolic acid
5-L-oxoproline
5-oxo-L-proline
L-proline, 5-oxo-
(-)-pyroglutamic acid
(S)-pyroglutamic acid
(2S)-5-oxopyrrolidine-2-carboxylic acid
(S)-5-oxopyrrolidine-2-carboxylic acid
(5S)-2-oxopyrrolidine-5-carboxylate
(2S)-5-oxopyrrolidine-5-carboxylic acid
(5S)-2-oxopyrrolidine-5-carboxylic acid
2-oxopyrrolidine-5(S)-carboxylate
2-oxopyrrolidine-5(S)-carboxylic acid
(S)-5-oxo-2-pyrrolidinecarboxylate
L-5-oxo-2-pyrrolidinecarboxylate
(S)-5-oxo-2-pyrrolidinecarboxylic acid
(S)-(-)-2-pyrrolidinone-5-carboxylic Acid
L-pyrrolidinonecarboxylate
(S)-(-)-2-pyrrolidone-5-carboxylate
L-2-pyrrolidone-5-carboxylate
(S)-(-)-2-pyrrolidone-5-carboxylic acid
(S)-2-pyrrolidone-5-carboxylic acid
2-L-pyrrolidone-5-carboxylic acid
2-laevo-pyrrolidone-5-carboxylic acid
L-pyrrolidonecarboxylate

Articles:

PubMed:Monitoring the ripening process of Cheddar cheese based on hydrophilic component profiling using gas chromatography-mass spectrometry.
PubMed:A simultaneous assay method for L-glutamate and L-pyroglutamate contents in soy sauce using a 5-oxoprolinase (without ATP hydrolyzing activity).
PubMed:Flavor characteristics of glutathione in raw and cooked foodstuffs.
PubMed:Targeted metabolomics for Aspergillus oryzae-mediated biotransformation of soybean isoflavones, showing variations in primary metabolites.
PubMed:Water sensor ppk28 modulates Drosophila lifespan and physiology through AKH signaling.
PubMed:Stability of monosodium glutamate in green table olives and pickled cucumbers as a function of packing conditions and storage time.
PubMed:Isotopic variants of light and heavy L-pyroglutamic acid succinimidyl esters as the derivatization reagents for DL-amino acid chiral metabolomics identification by liquid chromatography and electrospray ionization mass spectrometry.
PubMed:Role of adipokinetic hormone in stimulation of salivary gland activities: the fire bug Pyrrhocoris apterus L. (Heteroptera) as a model species.
PubMed:Identification of pyroglutamyl peptides in Japanese rice wine (sake): presence of hepatoprotective pyroGlu-Leu.
PubMed:Melanin-concentrating hormone (MCH) and gonadotropin-releasing hormones (GnRH) in Atlantic cod, Gadus morhua: tissue distributions, early ontogeny and effects of fasting.
PubMed:Monitoring the ripening process of Cheddar cheese based on hydrophilic component profiling using gas chromatography-mass spectrometry.
PubMed:Ingestion of low dose pyroglutamyl leucine improves dextran sulfate sodium-induced colitis and intestinal microbiota in mice.
PubMed:Selection of discriminant markers for authentication of Asian palm civet coffee (Kopi Luwak): a metabolomics approach.
PubMed:Obesity-related metabolomic analysis of human subjects in black soybean peptide intervention study by ultraperformance liquid chromatography and quadrupole-time-of-flight mass spectrometry.
PubMed:Preventive effect of pidotimod on reactivated toxoplasmosis in mice.
PubMed:Identification of a hepatoprotective peptide in wheat gluten hydrolysate against D-galactosamine-induced acute hepatitis in rats.
PubMed:Suppression of conditioned odor approach by feeding is independent of taste and nutritional value in Drosophila.
PubMed:Efficient production and characterization of the sweet-tasting brazzein secreted by the yeast Pichia pastoris.
PubMed:Gustatory perception and fat body energy metabolism are jointly affected by vitellogenin and juvenile hormone in honey bees.
PubMed:Food-restricted and dehydrated-induced anorexic rats present differential TRH expression in anterior and caudal PVN. Role of type 2 deiodinase and pyroglutamyl aminopeptidase II.
PubMed:Adipokinetic hormones (AKHs) of sphingid Lepidoptera, including the identification of a second M. sexta AKH.
PubMed:Determination of nonprotein amino acids and betaines in vegetable oils by flow injection triple-quadrupole tandem mass spectrometry: a screening method for the detection of adulterations of olive oils.
PubMed:The effect of adipokinetic hormone on midgut characteristics in Pyrrhocoris apterus L. (Heteroptera).
PubMed:Isolation and identification of the umami enhancing compounds in Japanese soy sauce.
PubMed:Angiotensin II type 1 receptor signaling regulates feeding behavior through anorexigenic corticotropin-releasing hormone in hypothalamus.
PubMed:[Role of the brain in the regulation of metabolism and energy expenditure: the central role of insulin, and insulin resistance of the brain].
PubMed:Metabolomics revealed novel isoflavones and optimal cultivation time of Cordyceps militaris fermentation.
PubMed:Synthesis of amino acid conjugates to 2-imino-3-methylene-5-carboxypyrrolidine and 2-imino-3-methylene-6-carboxypiperidine.
PubMed:Metabolomics analysis reveals the compositional differences of shade grown tea (Camellia sinensis L.).
PubMed:Effect of anorexinergic peptides, cholecystokinin (CCK) and cocaine and amphetamine regulated transcript (CART) peptide, on the activity of neurons in hypothalamic structures of C57Bl/6 mice involved in the food intake regulation.
PubMed:Lamprey GnRH-III releases luteinizing hormone but not follicle stimulating hormone in pigs.
PubMed:Production of shelf-stable ranch dressing using high-pressure processing.
PubMed:Characterization of low-molecular-weight antiyeast metabolites produced by a food-protective Lactobacillus-Propionibacterium coculture.
PubMed:Gastric electrical stimulation for obesity: the need for a new device using wider pulses.
PubMed:Natural variation in plasticity of glucose homeostasis and food intake.
PubMed:Age-dependent changes of fat body stores and the regulation of fat body lipid synthesis and mobilisation by adipokinetic hormone in the last larval instar of the cricket, Gryllus bimaculatus.
PubMed:Comparative peptidomics of four related hemipteran species: pyrokinins, myosuppressin, corazonin, adipokinetic hormone, sNPF, and periviscerokinins.
PubMed:Differential response of TRHergic neurons of the hypothalamic paraventricular nucleus (PVN) in female animals submitted to food-restriction or dehydration-induced anorexia and cold exposure.
PubMed:[AMPK, an active player in the control of metabolism].
PubMed:Psychoneuroendocrinology of anorexia nervosa.
PubMed:Unfolding of the immunoglobulin light and heavy chains is required for the enzymatic removal of N-terminal pyroglutamyl residues.
PubMed:Adipokinetic hormone-induced mobilization of fat body triglyceride stores in Manduca sexta: role of TG-lipase and lipid droplets.
PubMed:Occurrence of the free and Peptide forms of pyroglutamic acid in plasma from the portal blood of rats that had ingested a wheat gluten hydrolysate containing pyroglutamyl peptides.
PubMed:Brainstem thyrotropin-releasing hormone regulates food intake through vagal-dependent cholinergic stimulation of ghrelin secretion.
PubMed:Day-night differences in membrane-bound pyroglutamyl-2-naphthylamide-hydrolyzing activity in rat hypothalamus, pituitary, and retina.
PubMed:Wing morph-specific differences in the metabolism and endocrine control of reserve mobilization in adult males of a flightless bug, Pyrrhocoris apterus (L.) (Heteroptera).
PubMed:Chronic ethanol or glucose consumption alter TRH content and pyroglutamyl aminopeptidase II activity in rat limbic regions.
PubMed:AKH-producing neuroendocrine cell ablation decreases trehalose and induces behavioral changes in Drosophila.
PubMed:Glutamine in commercial liquid nutritional products.
PubMed:Hemolymph sugar homeostasis and starvation-induced hyperactivity affected by genetic manipulations of the adipokinetic hormone-encoding gene in Drosophila melanogaster.
PubMed:Identification of leucomyosuppressin in the German cockroach, Blattella germanica, as an inhibitor of food intake.
PubMed:Pressure/temperature combined treatments of precursors yield hormone-like peptides with pyroglutamate at the N terminus.
PubMed:[Reproductive toxicity of metadoxine in rats].
PubMed:Central administration of thyrotropin releasing hormone (TRH) and related peptides inhibits feeding behavior in the Siberian hamster.
PubMed:Isolation and identification of indigestible pyroglutamyl peptides in an enzymatic hydrolysate of wheat gluten prepared on an industrial scale.
PubMed:Production of pyroglutamic acid by thermophilic lactic acid bacteria in hard-cooked mini-cheeses.
PubMed:13C breath tests in infections and beyond.
PubMed:Agouti-related protein (AGRP) has a central inhibitory action on the hypothalamic-pituitary-thyroid (HPT) axis; comparisons between the effect of AGRP and neuropeptide Y on energy homeostasis and the HPT axis.
PubMed:Characterization of cigar tobaccos by gas chromatographic/mass spectrometric analysis of nonvolatile organic acids: application to the authentication of Cuban cigars.
PubMed:A simultaneous assay method for L-glutamate and L-pyroglutamate contents in soy sauce using a 5-oxoprolinase (without ATP hydrolyzing activity).
PubMed:Pyroglutamic acid in cheese: presence, origin, and correlation with ripening time of Grana Padano cheese.
PubMed:Oxoproline kinetics and oxoproline urinary excretion during glycine- or sulfur amino acid-free diets in humans.
PubMed:Quantitative analysis of pyroglutamic acid in peptides
PubMed:Quantitative analysis of pyroglutamic acid in peptides.
PubMed:Plasma L-5-oxoproline carbon and nitrogen kinetics in healthy young adults.
PubMed:Dietary protein, growth and urea kinetics in severely malnourished children and during recovery.
PubMed:Isolation, characterization and biological activity of a diuretic myokinin neuropeptide from the housefly, Musca domestica.
PubMed:Effect of long-term food restriction on pituitary sensitivity to cLHRH-I in broiler breeder females.
PubMed:Influence of Three Contrasting Detrital Carbon Sources on Planktonic Bacterial Metabolism in a Mesotrophic Lake.
PubMed:The effect of food intake from 2 to 24 weeks of age on LHRH-I content in the median eminence and gonadotrophin levels in pituitary and plasma in female broiler breeder chickens.
PubMed:Flavor characteristics of glutathione in raw and cooked foodstuffs.
PubMed:Chemical attributes characterizing sticky post-mortem ageing in beef.
PubMed:Urinary excretion of the TRH-like peptide pyroglutamyl-glutamyl-prolineamide in rats.
PubMed:Further evidence that the tachykinin PG-KII is a potent agonist at central NK-3, but not NK-1, receptors.
PubMed:Urinary excretion of 5-L-oxoproline (pyroglutamic acid) is increased during recovery from severe childhood malnutrition and responds to supplemental glycine.
PubMed:Effects of long-term food reduction on the hypothalamus-pituitary-thyroid axis in male and female rats.
PubMed:[Changes in chemical composition of tomatoes during processing].
PubMed:Neuronal control of development in hydra.
PubMed:Rapid gas chromatographic screening of edible seeds, nuts and beans for non-protein and protein amino acids.
PubMed:Starvation-induced changes in the hypothalamic content of prothyrotrophin-releasing hormone (proTRH) mRNA and the hypothalamic release of proTRH-derived peptides: role of the adrenal gland.
PubMed:Capillary gas chromatographic determination of proteins and biological amino acids as N(O)-tert.-butyldimethylsilyl derivatives.
PubMed:Effect of food on the bioavailability of pidotimod in healthy volunteers.
PubMed:Different effects of continuous infusion of interleukin-1 and interleukin-6 on the hypothalamic-hypophysial-thyroid axis.
PubMed:Effect of food deprivation and altered thyroid status on the hypothalamic-pituitary-thyroid axis in the rat.
PubMed:Inhibition of hypothalamic thyrotropin-releasing hormone messenger ribonucleic acid during food deprivation.
PubMed:Satiation due to CCK-8 derivative infusion into VMH is related to a specific macronutrient selection.
PubMed:Availability of cysteine and of L-2-oxo-thiazolidine-4-carboxylic acid as a source of cysteine in intravenous nutrition.
PubMed:Isolation of an anorexigenic protein from membranes.
PubMed:Molecular cloning and expression of bovine kappa-casein in Escherichia coli.
PubMed:Food intake suppression in rats by a substance isolated from human feces.
PubMed:Thyrotropin-releasing hormone (TRH) acts centrally to stimulate gastric contractility in rats.
PubMed:Effects of analogs of (pyro)Glu-His-Gly-OH on food consumption and gastric acid secretion in rats.
PubMed:Drinking and feeding inhibition by ICV pulse injection or infusion of bombesin, ranatensin and litorin to rats.
PubMed:Action of anorexigenic peptide injected into the brain: dissociation of effect on body weight and feeding in the rat.
PubMed:Lack of effect of the peptide pyro-Glu-His-Gly-OH on food consumption in mice and rats.
PubMed:No proof of anorectic properties of pGlu-His-Gly in rats and mice.
PubMed:Use of perfluoroalkanoic acids as volatile ion pairing reagents in preparative HPLC.
PubMed:Synthesis and assay for activity of a proposed anorexogenic agent, L-pyroglutamyl-L-histidyl-glycine.
PubMed:Stimulation of canine pancreatic polypeptide, gastrin, and gastric acid secretion by ranatensin, litorin, bombesin nonapeptide and substance P.
PubMed:Experiments with a reported anorexigenic tripeptide: pyro-Glu-His-Gly-OH.
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