P2519
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:
Molecular Weight:
129.16
Beilstein:
81093
EC Number:
MDL number:
UNSPSC Code:
12352106
PubChem Substance ID:
NACRES:
NA.26
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Product Name
L-Pipecolic acid, 99% (titration)
Quality Level
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.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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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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