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P1645

Sigma-Aldrich

Palmitoyl-L-carnitine chloride

≥98% (TLC), powder

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Synonym(s):
O-Palmitoyl-L-carnitine chloride
Linear Formula:
C23H46NO4 · Cl
CAS Number:
18877-64-0
Molecular Weight:
436.07
Beilstein:
4071005
EC Number:
242-642-6
MDL number:
MFCD00070346
PubChem Substance ID:
24898229
NACRES:
NA.25

Quality Level

200

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

Signal Word

Warning

Hazard Statements

H315 - H319 - H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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)
Evan L Brittain et al.
Circulation, 133(20), 1936-1944 (2016-03-24)
The mechanisms of right ventricular (RV) failure in pulmonary arterial hypertension (PAH) are poorly understood. Abnormalities in fatty acid (FA) metabolism have been described in experimental models of PAH, but systemic and myocardial FA metabolism has not been studied in
J B Shen et al.
The American journal of physiology, 268(3 Pt 2), H1027-H1036 (1995-03-01)
We previously showed that palmitoyl-L-carnitine (L-PC) inhibits the Na/K pump current (INa/K). In the present report, we test the hypothesis that L-PC, like ouabain, should increase myocyte shortening. Membrane potentials or ionic currents were recorded simultaneously with cell shortening in
C Y Xiao et al.
Basic research in cardiology, 92(5), 320-330 (1998-03-05)
Long-chain acylcarnitines, such as palmitoyl-L-carnitine (PALCAR), are known to accumulate in the myocardium during ischemia. We examined whether exogenous PALCAR modifies the myocardial levels of high-energy phosphates (HEP) and free fatty acids (FFA) in the heart, and whether d-cis-diltiazem and
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
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