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Merck

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:
25597-09-5
Molecular Weight:
427.66
MDL number:
MFCD28902307
UNSPSC Code:
12352211
PubChem Substance ID:
329759399
NACRES:
NA.26
Beilstein/REAXYS Number:
7309670

Product Name

Stearoyl-L-carnitine, ≥97.0% (TLC)

SMILES string

C[N+](C)(C)C[C@H](OC(CCCCCCCCCCCCCCCCC)=O)CC([O-])=O

InChI key

FNPHNLNTJNMAEE-HSZRJFAPSA-N

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

assay

≥97.0% (TLC)

optical activity

[α]/D -15±2°, c = 1 in methanol

impurities

≤10% water

storage temp.

2-8°C

Quality Level

100

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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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
BCCF8632
BCBT2875
BCBP5279V
BCBP5279

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Jie An et al.
Nature medicine, 10(3), 268-274 (2004-02-11)
Lipid infusion or ingestion of a high-fat diet results in insulin resistance, but the mechanism underlying this phenomenon remains unclear. Here we show that, in rats fed a high-fat diet, whole-animal, muscle and liver insulin resistance is ameliorated following hepatic
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)
M S Rashed et al.
Pediatric research, 38(3), 324-331 (1995-09-01)
Acylcarnitine profiling from blood or plasma samples by electrospray tandem mass spectrometry (ESI-MS/MS) has been recognized recently as a useful tool in the biochemical diagnosis of propionic acidemia, methylmalonic acidemia together with short-chain and medium-chain acyl-CoA dehydrogenase deficiencies. In the
Elizabeth C Randall et al.
Cancer research, 80(6), 1258-1267 (2019-11-27)
Glioblastoma (GBM) is increasingly recognized as a disease involving dysfunctional cellular metabolism. GBMs are known to be complex heterogeneous systems containing multiple distinct cell populations and are supported by an aberrant network of blood vessels. A better understanding of GBM
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