P2519

Sigma-Aldrich

L-Pipecolic acid

99% (titration)

Synonym(s):
(S)-(−)-2-Piperidinecarboxylic acid, L-Homoproline
Empirical Formula (Hill Notation):
C6H11NO2
CAS Number:
Molecular Weight:
129.16
Beilstein/REAXYS Number:
81093
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.26

Quality Level

assay

99% (titration)

form

powder

application(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).

Packaging

100, 250 mg in glass insert
1 g in glass bottle

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.

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. P2519.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Target Organs

Respiratory system

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Certificate of Analysis

Certificate of Origin

Transcriptional analysis of defense mechanisms in upland tetraploid switchgrass to greenbugs
Donze-Reiner T, et al.
BMC plant biology, 17(1), 46-46 (2017)
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...
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...
Pipecolic acid
Laboratory Guide to the Methods in Biochemical Genetics (2008)
M R Baumgartner et al.
Annals of neurology, 47(1), 109-113 (2000-01-13)
We describe an 18-year-old patient with psychomotor retardation and abnormally short metatarsi and metacarpals but no other signs of classic Refsum disease. Molecular analysis of the phytanoyl-coenzyme A hydroxylase gene revealed a homozygous deletion causing a frameshift. Surprisingly, L-pipecolic acid...

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