Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

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

Looking for similar products? Visit Product Comparison Guide

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
BCCF8632
BCBT2875
BCBP5279V
BCBP5279

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
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
William C Hallows et al.
Molecular cell, 41(2), 139-149 (2011-01-25)
Emerging evidence suggests that protein acetylation is a broad-ranging regulatory mechanism. Here we utilize acetyl-peptide arrays and metabolomic analyses to identify substrates of mitochondrial deacetylase Sirt3. We identified ornithine transcarbamoylase (OTC) from the urea cycle, and enzymes involved in β-oxidation.
R J Morrow et al.
Clinica chimica acta; international journal of clinical chemistry, 211(1-2), 73-81 (1992-10-15)
Carnitine esters from acetylcarnitine (C2 acyl chain) to octadecanoylcarnitine (C18 acyl chain) can be extracted from urine with recoveries of greater than 80%. However, to obtain such recoveries, it is important to choose the method of extraction appropriate to the
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service