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pipecolinic acid

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Name:piperidine-2-carboxylic acid
CAS Number: 535-75-1Picture of molecule3D/inchi
Other(deleted CASRN):4043-87-2
ECHA EINECS - REACH Pre-Reg:208-616-3
FDA UNII: H254GW7PVV
Nikkaji Web:J1.592J
Beilstein Number:0081095
MDL:MFCD00064347
XlogP3:-2.30 (est)
Molecular Weight:129.15907000
Formula:C6 H11 N O2
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
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
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Soluble in:
 water, 7.406e+004 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
DL-Pipecolinic acid 97%
Sigma-Aldrich: Aldrich
For experimental / research use only.
Pipecolinic Acid 98%
sds
TCI AMERICA
For experimental / research use only.
DL-Pipecolic Acid >98.0%(T)
sds
 
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
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for pipecolinic acid usage levels up to:
 not for fragrance use.
 
Recommendation for pipecolinic acid flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA GENetic TOXicology:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :849
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
piperidine-2-carboxylic acid
Chemidplus:0000535751
RTECS:TK6021000 for cas# 535-75-1
 
References:
 piperidine-2-carboxylic acid
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):849
Pubchem (cas):535-75-1
 
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
Metabolomics Database:Search
KEGG (GenomeNet):C00408
HMDB (The Human Metabolome Database):HMDB00070
FooDB:FDB000545
YMDB (Yeast Metabolome Database):YMDB01338
Export Tariff Code:2933.39.9100
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 apple plant
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 banana fruit
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 bean adzuki bean seed
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 bean black bean seed
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 bean fava bean seed
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 bean field bean
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 carrot plant
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 cherry sour cherry fruit
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 date palm fruit
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 eggplant fruit
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 ginger rhizome
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 lupine white lupine stem
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 melon bitter melon fruit
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 pea plant
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 tamarind fruit
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 tea fruit
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 tomato fruit
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 zingiber officinale root oil china @ 0.10%
Data GC Search Trop Picture
 
Synonyms:
 dihydrobaikiane
 hexahydropicolinic acid
 pipecolic acid
2-piperidine carboxylic acid
 piperidine-2-carboxylic acid
homoproline
 

Articles:

PubMed:The betaine profile of cereal flours unveils new and uncommon betaines.
PubMed:Heat-induced formation of mepiquat by decarboxylation of pipecolic acid and its betaine derivative. Part 2: Natural formation in cooked vegetables and selected food products.
PubMed:Heat-induced formation of mepiquat by decarboxylation of pipecolic acid and its betaine derivative. Part 1: Model system studies.
PubMed:Development, synthesis and structure-activity-relationships of inhibitors of the macrophage infectivity potentiator (Mip) proteins of Legionella pneumophila and Burkholderia pseudomallei.
PubMed:Inhibitors of macrophage infectivity potentiator-like PPIases affect neisserial and chlamydial pathogenicity.
PubMed:Regulatory effects of the L-lysine metabolites, L-2-aminoadipic acid and L-pipecolic acid, on protein turnover in C2C12 myotubes.
PubMed:Enantiomeric separation of non-protein amino acids by electrokinetic chromatography.
PubMed:Homostachydrine (pipecolic acid betaine) as authentication marker of roasted blends of Coffea arabica and Coffea canephora (Robusta) beans.
PubMed:Short-term toxicity assessments of an antibiotic metabolite in Wistar rats and its metabonomics analysis by ultra-high performance liquid chromatography coupled to quadrupole time-of-flight mass spectrometry.
PubMed:Betaines and related ammonium compounds in chestnut (Castanea sativa Mill.).
PubMed:Amino acid-derived betaines dominate as urinary markers for rye bran intake in mice fed high-fat diet--A nontargeted metabolomics study.
PubMed:Identification and monitoring of metabolite markers of dry bean consumption in parallel human and mouse studies.
PubMed:Regulation of free glutamate content in meat by dietary lysine in broilers.
PubMed:Determination and stereochemistry of proteinogenic and non-proteinogenic amino acids in Saudi Arabian date fruits.
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:Occurrence of pipecolic acid and pipecolic acid betaine (homostachydrine) in Citrus genus plants.
PubMed:Metabolomic analysis of meju during fermentation by ultra performance liquid chromatography-quadrupole-time of flight mass spectrometry (UPLC-Q-TOF MS).
PubMed:Pipecolic acid derivatives as small-molecule inhibitors of the Legionella MIP protein.
PubMed:Metabolomic analysis of livers and serum from high-fat diet induced obese mice.
PubMed:A novel yellow pigment, furpipate, derived from lysine and furfural.
PubMed:Browning of furfural and amino acids, and a novel yellow compound, furpipate, formed from lysine and furfural.
PubMed:Applications of the ninhydrin reaction for analysis of amino acids, peptides, and proteins to agricultural and biomedical sciences.
PubMed:Discrimination between arabica and robusta coffee species on the basis of their amino acid enantiomers.
PubMed:Central pipecolic acid increases food intake under ad libitum feeding conditions in the neonatal chick.
PubMed:Intracerebroventricular administration of GABA-A and GABA-B receptor antagonists attenuate feeding and sleeping-like behavior induced by L-pipecolic acid in neonatal chicks.
PubMed:Determination of D- and L-pipecolic acid in food samples including processed foods.
PubMed:Intracerebroventricular injection of pipecolic acid inhibits food intake and induces sleeping-like behaviors in the neonatal chick.
PubMed:New and Convenient Syntheses of the Important Roasty, Popcorn-like Smelling Food Aroma Compounds 2-Acetyl-1-pyrroline and 2-Acetyltetrahydropyridine from Their Corresponding Cyclic alpha-Amino Acids.
PubMed:Osmoprotectants and cryoprotectants for Listeria monocytogenes.
PubMed:Origin of D- and L-pipecolic acid in human physiological fluids: a study of the catabolic mechanism to pipecolic acid using the lysine loading test.
PubMed:GABA in the nucleus accumbens shell participates in the central regulation of feeding behavior.
PubMed:Rapid gas chromatographic screening of edible seeds, nuts and beans for non-protein and protein amino acids.
PubMed:Analysis of free amino acids in green coffee beans. I. Determination of amino acids after precolumn derivatization using 9-fluorenylmethylchloroformate.
PubMed:GABA transmission, but not benzodiazepine receptor stimulation, modulates ethanol intake by rats.
PubMed:[On the chemotaxonomy of food plants :pipecolinic acid, a characteristic ingredient of grass silages].
PubMed:Proline control of the feeding reaction of Cordylophora.
 
Notes:
Pipecolic acid is a metabolite of lysine found in human physiological fluids such as urine, plasma and CSF. However, it is uncertain if pipecolic acid originates directly from food intake or from mammalian or intestinal bacterial enzyme metabolism. Recent studies suggest that plasma pipecolic acid, particularly the D-isomer, originates mainly from the catabolism of dietary lysine by intestinal bacteria rather than by direct food intake. In classic Zellweger syndrome (a cerebro-hepato-renal genetic disorder, OMIM 214100) pipecolic acid accumulate in the plasma of the patients. It is known that plasma pipecolic acid levels are also elevated in patients with chronic liver diseases. Pipecolic acid is moderately elevated in patients with pyridoxine-dependent seizures and might therefore be a possible biochemical marker for selecting candidates for pyridoxine therapy (Plecko et al 2000). Pipecolic acid was also elevated in CSF in these vitamin B6-responsive patients. (PMID 12705501) [HMDB]
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