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P2519

Sigma-Aldrich

L-Pipecolic acid

99% (titration), suitable for GC/MS

Synonym(s):

(S)-(−)-2-Piperidinecarboxylic acid, L-Homoproline

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About This Item

Empirical Formula (Hill Notation):
C6H11NO2
CAS Number:
3105-95-1
Molecular Weight:
129.16
Beilstein/REAXYS Number:
81093
EC Number:
221-462-1
MDL number:
MFCD00005981
UNSPSC Code:
12352106
PubChem Substance ID:
24898330
NACRES:
NA.26

product name

L-Pipecolic acid, 99% (titration)

Quality Level

200

assay

99% (titration)

form

powder

technique(s)

GC/MS: suitable

color

white

mp

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

InChI key

HXEACLLIILLPRG-YFKPBYRVSA-N

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General description

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

Application

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

Biochem/physiol Actions

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.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

wgk_germany

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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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