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Safety Information

61229

Sigma-Aldrich

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
Beilstein:
7309670
MDL number:
MFCD28902307
UNSPSC Code:
12352211
PubChem Substance ID:
329759399
NACRES:
NA.26

Quality Level

100

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

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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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

61229-VAR:
61229-50MG:
61229-10MG:
61229-BULK:

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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)
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
M Möder et al.
Analytical and bioanalytical chemistry, 375(2), 200-210 (2003-02-01)
l-Carnitine and its esters are products of intermediary metabolism of organisms. The distribution pattern or the favored excretion of individual acylcarnitines tells something about metabolic diseases. The determination of the urinary acylcarnitine pattern by flow injection analysis (FIA)-electrospray ionization (ESI)-mass
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