Basic information Safety Supplier Related

STEAROYL-L-CARNITINE

Basic information Safety Supplier Related

STEAROYL-L-CARNITINE Basic information

Product Name:
STEAROYL-L-CARNITINE
Synonyms:
  • STEAROYL-L-CARNITINE
  • Stearoyl-L-carnitine-[d3] (Solution)
  • Stearoyl-L-carnitine >=97.0% (TLC)
  • (R)-3-(Stearoyloxy)-4-(trimethylammonio)butanoate
  • Stearoyl-L-carnitine in Methanol
  • Stearoylcarnitine, 10 mM in DMSO
  • Stearoyl-L-carnitine
CAS:
25597-09-5
MF:
C25H49NO4
MW:
427.66086
Mol File:
25597-09-5.mol
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STEAROYL-L-CARNITINE Chemical Properties

storage temp. 
2-8°C
solubility 
Water: 1 mg/mL (2.34 mM; ultrasonic and warming and heat to 80°C); DMSO: < 1 mg/mL (insoluble or slightly soluble)
form 
Solid
color 
White to off-white
optical activity
[α]/D -15±2°, c = 1 in methanol
BRN 
7309670
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STEAROYL-L-CARNITINE Usage And Synthesis

Uses

Stearoyl-L-carnitine may be used as an analytical reference standard for the quantification of the analyte in biological fluids using chromatography-based techniques.

Definition

ChEBI: O-octadecanoyl-L-carnitine is an O-acyl-L-carnitine in which the acyl group is specified as stearoyl (octadecanoyl). It has a role as a human metabolite. It is functionally related to an octadecanoic acid.

General Description

Stearoyl-L-carnitine is a naturally occurring compound belonging to the acylcarnitine class of compounds as listed in the human metabolome database (HMBD). These compounds are reported to be used as biomarkers in the diagnosis of carnitine deficiency. It acts as a carrier of long chain acyl groups from activated fatty acids across the inner mitochondrial membrane into the mitochondrial matrix where they undergo β-oxidation to acetyl CoA to obtain usable energy via the citric acid cycle.

Biochem/physiol Actions

Stearoylcarnitine is found in significantly greater amounts in patients with carnitine palmitoyltransferase II deficiency. Carnitine palmitoyltransferase, in conjunction with acyl-CoA synthetase and carnitine/acylcarnitine translocase, provides the mechanism whereby long-chain fatty acids are transferred from the cytosol to the mitochondrial matrix to undergo beta-oxidation.

in vivo

Stearoylcarnitine increases in the cortex, striatum/thalamus, and cerebellum in CD1 mouse pups (postnatal day 9) with hypoxic-ischemic brain injury (HIBI) induced by carotid artery ligation[2].
Stearoylcarnitine (500 μM, 0-40 min) shows inhibitory towards lecithin cholesterol acyltransferase (LCAT) in rat and rabbits plasma, but not in human plasma[3].
Stearoylcarnitine is characterized as one of potential biomarkers involved in the pathogenesis of Parkinson’s disease (PD) [4].

IC 50

Human Endogenous Metabolite

STEAROYL-L-CARNITINESupplier

Sigma-Aldrich
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