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Palmitoyl-L-Carnitine Chloride

Product NamePalmitoyl-L-Carnitine Chloride
CAS18877-64-0
MFC23H46ClNO4
MW436.07
EINECS242-642-6
MOL File18877-64-0.mol

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
Storage Class	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

MSDS

Provider	Language
SigmaAldrich	English

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

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.

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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