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Merck
CN

237752

L-Pipecolic acid

Proline homolog., 99%

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
EC Number:
221-462-1
UNSPSC Code:
12352200
PubChem Substance ID:
329752502
Beilstein/REAXYS Number:
81093
MDL number:
MFCD00005981

Key Documents

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InChI key

HXEACLLIILLPRG-YFKPBYRVSA-N

InChI

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

SMILES string

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

assay

99%

form

powder with small lumps

optical activity

[α]25/D −26.4°, c = 1 in H2O

color

white

mp

272 °C (lit.)

application(s)

peptide synthesis

storage temp.

2-8°C

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General description

Occurs in seeds, malt, edible mushrooms, fruits, etc.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
09814LE
13609BF
10906MG
08107JN
03522BW

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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
D W Armstrong et al.
Journal of pharmaceutical and biomedical analysis, 11(10), 881-886 (1993-10-01)
Recently it was found that normal adults excrete pipecolic acid primarily as the D-enantiomer even though it is present in the blood stream mainly as the L-enantiomer (i.e. > 98% L). This study of pipecolic acid stereochemistry was extended to
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
Susan Keay et al.
Chemical biology & drug design, 77(6), 421-430 (2011-03-01)
Interstitial cystitis/painful bladder syndrome is a chronic bladder disorder with epithelial thinning or ulceration, pain, urinary frequency and urgency, for which there is no reliably effective therapy. We previously reported that interstitial cystitis/painful bladder syndrome bladder epithelial cells make a
Kuo-Yuan Hung et al.
The Journal of organic chemistry, 75(24), 8728-8731 (2010-11-26)
An efficient stereoselective synthesis of fully protected (2S,4R)-4-methylpipecolic acid has been developed. The synthesis was achieved by initial asymmetric α-alkylation of glycine with a chiral iodide, affording the linear precursor as a single stereoisomer. Subsequent aldehyde formation using OsO(4)/NaIO(4) followed
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