61229
Stearoyl-L-carnitine
≥97.0% (TLC)
Synonym(s):
(2R)-3-Carboxy-N,N,N-trimethyl-2-[(1-oxooctadecyl)oxy]-1-propanaminium inner salt, L-Carnitine octadecanoyl ester, C18-Carnitine, Octadecanoyl-L-carnitine
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About This Item
Empirical Formula (Hill Notation):
C25H49NO4
CAS Number:
Molecular Weight:
427.66
MDL number:
UNSPSC Code:
12352211
PubChem Substance ID:
NACRES:
NA.26
Beilstein/REAXYS Number:
7309670
Assay:
≥97.0% (TLC)
Quality level:
Quality Level
assay
≥97.0% (TLC)
optical activity
[α]/D -15±2°, c = 1 in methanol
impurities
≤10% water
storage temp.
2-8°C
SMILES string
C[N+](C)(C)C[C@H](OC(CCCCCCCCCCCCCCCCC)=O)CC([O-])=O
InChI
1S/C25H49NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-25(29)30-23(21-24(27)28)22-26(2,3)4/h23H,5-22H2,1-4H3/t23-/m1/s1
InChI key
FNPHNLNTJNMAEE-HSZRJFAPSA-N
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.
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Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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Yosuke Shigematsu et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 792(1), 63-72 (2003-06-28)
In a selective screening for fatty acid oxidation disorders by tandem mass spectrometry, we tested the diagnostic ratios and acylcarnitine concentrations in sera or blood spots, which were reported to be specific to very long-chain acyl CoA dehydrogenase deficiency, carnitine
Global profiling of the muscle metabolome: method optimization, validation and application to determine exercise-induced metabolic effects.
Alves, R.D.A.M, et al.
Metabolomics, 11, 271-285 (2015)
C Vianey-Saban et al.
Clinica chimica acta; international journal of clinical chemistry, 269(1), 43-62 (1998-03-14)
Very-long-chain acyl-CoA dehydrogenase (VLCAD) is an enzyme catalyzing the dehydrogenation of long-chain fatty acids in the first step of mitochondrial fatty acid oxidation. Using an ETF (electron transfer flavoprotein, the physiological electron acceptor of VLCAD) reduction assay, we identified VLCAD