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Merck

P2519

Sigma-Aldrich

L-Pipecolsäure

99% (titration)

Synonym(e):

(S)-(−)-2-Piperidincarbonsäure, L-Homoprolin

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About This Item

Empirische Formel (Hill-System):
C6H11NO2
CAS-Nummer:
Molekulargewicht:
129.16
Beilstein:
81093
EG-Nummer:
MDL-Nummer:
UNSPSC-Code:
12352106
PubChem Substanz-ID:
NACRES:
NA.26

Qualitätsniveau

Assay

99% (titration)

Form

powder

Methode(n)

GC/MS: suitable

Farbe

white

mp (Schmelzpunkt)

272 °C (lit.)

SMILES String

OC(=O)[C@@H]1CCCCN1

InChI

1S/C6H11NO2/c8-6(9)5-3-1-2-4-7-5/h5,7H,1-4H2,(H,8,9)/t5-/m0/s1

InChIKey

HXEACLLIILLPRG-YFKPBYRVSA-N

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Allgemeine Beschreibung

L-pipecolic acid (piperidine-2-carboxylic acid) is a nitrogen-containing heterocyclic compound. It is an imino acid. Its molecular weight is 129.2.

Anwendung

L-Pipecolic acid has been used as a standard for the quantification by gas chromatography-mass spectrometry (GC-MS).

Biochem./physiol. Wirkung

L-pipecolic acid is implicated in Zellweger syndrome. Pipecolic acid is also a plant defence metabolite. It is a signaling compound essential for systemic acquired resistance (SAR).
L-Pipecolic acid is a lysine metabolite; defect in its catabolism is involved in hyperpipecolic acidemia, cerebro-hepato-renal syndrome, neonatal onset adrenoleukodystrophy, and infantile Refsum disease.

Piktogramme

Exclamation mark

Signalwort

Warning

Gefahreneinstufungen

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Zielorgane

Respiratory system

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Persönliche Schutzausrüstung

dust mask type N95 (US), Eyeshields, Gloves


Analysenzertifikate (COA)

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Die Dokumentenbibliothek aufrufen

S J Mihalik et al.
The Journal of biological chemistry, 264(5), 2509-2517 (1989-02-15)
L-Pipecolic acid oxidation was studied in the rabbit and cynomolgus monkey. Tissue homogenates from both species incubated with L-[2,3,4,5,6-3H]pipecolic acid produced a single radioactive product identified as alpha-aminoadipic acid. In the rabbit, L-pipecolic acid oxidation was greatest in kidney cortex
Transcriptional analysis of defense mechanisms in upland tetraploid switchgrass to greenbugs
Donze-Reiner T, et al.
BMC plant biology, 17(1), 46-46 (2017)
Pipecolic acid
Laboratory Guide to the Methods in Biochemical Genetics (2008)
Ronald J A Wanders
American journal of medical genetics. Part A, 126A(4), 355-375 (2004-04-21)
The group of peroxisomal disorders now includes 17 different disorders with Zellweger syndrome as prototype. Thanks to the explosion of new information about the functions and biogenesis of peroxisomes, the metabolic and molecular basis of most of the peroxisomal disorders
S J Mihalik et al.
Pediatric research, 25(5), 548-552 (1989-05-01)
L-Pipecolic acid, a cyclic imino acid produced during the degradation of lysine, accumulates in body fluids of infants with the generalized peroxisomal disorders, including Zellweger syndrome, neonatal adrenoleukodystrophy, and infantile Refsum disease. Peroxisome-enriched fractions from normal human liver oxidized L-[3H]pipecolic

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