Palmitoyl-L-Carnitine Chloride Chemical Properties

Melting point:

168-172 °C(lit.)

storage temp. 

-20°C

solubility 

H₂O: 25 mg/mL with heat or sonication

form 

powder

color 

white

Appearance

white solid

Water Solubility 

H2O: 25mg/mL (with he at or sonication)

BRN 

4071005

InChI

InChI=1/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-;/s3

InChIKey

GAMKNLFIHBMGQT-GKNLIIIVNA-N

SMILES

[C@@H](CC(=O)O)(C[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCC.[Cl-] |&1:0,r|

CAS DataBase Reference

18877-64-0

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

F 

3-10

HS Code 

2923900090

MSDS

• Language:English Provider:SigmaAldrich

Palmitoyl-L-Carnitine Chloride Usage And Synthesis

Description

Hexadecanoylcarnitine, also called as palmitoyl-L-carnitine, is an endogenous acylcarnitine and acts as a key energy donor for β-oxidation. Hexanoylcarnitine chloride is used as an analytical standard in HPLC-MS and MS/MS studies.

Hexanoylcarnitine has surface activity, has a diphilic character and has detergent properties. Hexanoylcarnitine has surface activity, is diphilic and has detergent properties. Hexanoylcarnitine promotes the transfer of long-chain fatty acids from cytoplasm to mitochondria during fatty acid oxidation. The substance accumulates in the myocardium during ischemia and affects the levels of phosphate and free fatty acids in the myocardium and on the myocardial vascular endothelium. In experimental models, palmitoyl-L-carnitine levels increased with age and induced mitochondrial dysfunction in neurons.

Palmitoyl-L-carnitine may be used as an analytical standard to quantify the analyte in biological samples of patients with continuous ambulatory peritoneal dialysis (CAPD) or automated peritoneal dialysis (APD) using HPLC-MS. It may also be used as an analytical reference standard for the separation and identification of underivatized palmitoyl-L-carnitine in human plasma samples.

The product is used primarily as a control for MS/MS.

Chemical Properties

White crystalline powder

Uses

Palmitoyl-L-carnitine Hydrochloride is a long-chain fatty ester of carnitine which is accumulated and released into the circulation, in fatty-acid oxidation defects. Pattern of Lauroyl-L-carnitine can be diagnostic for a number of ?-oxidation defects.

Uses

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.

IC 50

Kir6.2; Human Endogenous Metabolite

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