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P1645

Sigma-Aldrich

Palmitoyl-L-carnitine chloride

≥98% (TLC), powder

Synonym(s):

O-Palmitoyl-L-carnitine chloride

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About This Item

Linear Formula:
C23H46NO4 · Cl
CAS Number:
18877-64-0
Molecular Weight:
436.07
Beilstein/REAXYS Number:
4071005
EC Number:
242-642-6
MDL number:
MFCD00070346
UNSPSC Code:
12352211
PubChem Substance ID:
24898229
NACRES:
NA.25

assay

≥98% (TLC)

form

powder

color

white

solubility

H2O: 25 mg/mL (with heat or sonication)

lipid type

saturated FAs

storage temp.

−20°C

SMILES string

[Cl-].CCCCCCCCCCCCCCCC(=O)O[C@H](CC(O)=O)C[N+](C)(C)C

InChI

1S/C23H45NO4.ClH/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23(27)28-21(19-22(25)26)20-24(2,3)4;/h21H,5-20H2,1-4H3;1H/t21-;/m1./s1

InChI key

GAMKNLFIHBMGQT-ZMBIFBSDSA-N

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Application

Palmitoyl-L-carnitine chloride has been used as acylcarnitine in treating cardiomyocytes for the induction of reactive oxygen species (ROS).

Biochem/physiol Actions

Long-chain acylcarnitine and well-known intermediate in mitochondrial fatty acid oxidation. Modifies myocardial levels of high-energy phosphates and free fatty acids in the heart. Increases erythroid colony formation in culture. Reduces surface negative charge of erythrocytes and myocytes. Reported to affect currents and inhibit endothelium-dependent relaxation induced by acetylcholine and substance P in a dose-dependent manner by suppressing the intracellular calcium signal transduction in endothelial cells. Inhibits the Na/K pump current but has no effect on the intracellular calcium current in guinea pig ventricular cells. However, like oubain, it reversibly depolarizes the resting membrane, decreases action potential duration, and increases the amplitude of myocyte contractions.

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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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Sexual dimorphism in myocardial acylcarnitine and triglyceride metabolism
Devanathan S, et al.
Biology of sex differences, 7(1), 25-25 (2016)
T Nakadate et al.
Cancer research, 47(24 Pt 1), 6537-6542 (1987-12-15)
Palmitoylcarnitine, a reported protein kinase C inhibitor, enhanced the phorbol ester dependency of the enzyme, augmenting protein kinase C activity in the presence of phorbol esters such as phorbol 12,13-dibutyrate while inhibiting the basal activity measured in the presence of
N Inoue et al.
Cardiovascular research, 28(1), 129-134 (1994-01-01)
Palmitoyl-L-carnitine, which accumulates in ischaemic myocardium, may influence the function of vascular endothelium in the ischaemic area. The aim of the study was therefore to examine the effect of palmitoyl-L-carnitine on endothelium dependent relaxations of rabbit thoracic aortas and its
C Gruver et al.
Journal of molecular and cellular cardiology, 25(10), 1275-1284 (1993-10-01)
1-Palmitoylcarnitine (1-PC) reduced the electrophoretic mobility of human erythrocytes bathed in low ionic strength solution. Unlike divalent cations which appear to reduce electrophoretic mobility by screening surface negative charge, cationic 1-PC does so by being incorporated into the plasma membrane.
Q Y Liu et al.
Biochemical and biophysical research communications, 228(2), 252-258 (1996-11-12)
We have studied the effect of a palmitoyl-L-carnitine (L-PC) on single cardiac L-type Ca channels incorporated from porcine ventricular sarcolemma into planar lipid bilayers where we could control the concentration, intracellular and/or extracellular location, and duration of L-PC treatment. We
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