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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:
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

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

WGK

WGK 3

Personal Protective Equipment

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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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)
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
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
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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