| Identification | Back Directory | [Name]
PALMITOYL-L-CARNITINE CHLORIDE | [CAS]
18877-64-0 | [Synonyms]
Einecs 242-642-6
L-CARNITINE:HCL, O-PALMITOYL
L-Palmitoylcarnitine chloride
PALMITOYL-L-CARNITINE CHLORIDE
O-PALMITOYL-L-CARNITINE CHLORIDE
HEXADECANOYL-L-CARNITINE CHLORIDE
Palmitoyl-L-carnitine hydrochloride
Palmitoyl-L-carnitine chloride≥ 99% (TLC)
(R)-3-(Palmitoyloxy)-4-(trimethylammonio)butanoate Hydrochloride
(R)-3-(Hexadecanoyloxy)-4-(trimethylammonio)butyrate Hydrochloride
(R)-[3-carboxy-2-[(1-oxohexadecyl)oxy]propyl]trimethylammonium chloride
1-Propanaminium, 3-carboxy-N,N,N-trimethyl-2-(1-oxohexadecyl)oxy-, chloride, (2R)-
1-Propanaminium, 3-carboxy-N,N,N-trimethyl-2-((1-oxohexadecyl)oxy)-, chloride, (R)- | [EINECS(EC#)]
242-642-6 | [Molecular Formula]
C23H46ClNO4 | [MDL Number]
MFCD00070346 | [MOL File]
18877-64-0.mol | [Molecular Weight]
436.07 |
| Chemical Properties | Back Directory | [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 |
| Hazard Information | Back Directory | [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. | [Enzyme inhibitor]
This naturally occurring acylated derivative (FW = 436.07 g/mol; CAS
18877-64-0) is an intermediate in the mitochondrial palmitic acid oxidation.
Palmitoyl-L-carnitine reduces negative charge of membrane surfaces, when
incorporated into the plasma membrane in erythrocytes and myocytes.
Note: Because this substance readily forms micelles, one must take care to
discriminate whether the monomeric and/or micelle form (s) is (are)
inhibitory, when present at concentrations above the critical micelle
concentration (cmc). Target (s) : 7-ethoxycoumarin O-deethylase,
cytochrome P450; lysophospholipase; [myosin light-chain] kinase
; Na+/K+-exchanging ATPase; palmitoyl-CoA hydrolase, or
acyl-CoA hydrolase); phosphatidylcholine:cholesterol
acyltransferase, LCAT; and protein kinase C. | [IC 50]
Kir6.2; Human Endogenous Metabolite | [storage]
Store at -20°C |
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