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61229

Sigma-Aldrich

Stearoyl-L-carnitine

≥97.0% (TLC)

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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
Empirical Formula (Hill Notation):
C25H49NO4
CAS Number:
Molecular Weight:
427.66
Beilstein:
7309670
PubChem Substance ID:
NACRES:
NA.26

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

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This Item
508926125161367
Stearoyl-L-carnitine ≥97.0% (TLC)

Sigma-Aldrich

61229

Stearoyl-L-carnitine

Octanoyl-L-carnitine ≥97.0% (TLC)

Sigma-Aldrich

50892

Octanoyl-L-carnitine

Palmitoyl-L-carnitine ≥97.0% (HPLC)

Sigma-Aldrich

61251

Palmitoyl-L-carnitine

Myristoyl-L-carnitine ≥97.0% (HPLC)

Sigma-Aldrich

61367

Myristoyl-L-carnitine

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

optical activity

[α]/D -15±2°, c = 1 in methanol

optical activity

[α]/D -17±2°, c = 0.1 in H2O

optical activity

[α]/D -17±2°, c = 1 in methanol

optical activity

[α]/D -18±2°, c = 1 in methanol

impurities

≤10% water

impurities

≤10% water

impurities

≤10% water

impurities

≤10% water

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


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Octanoyl-L-carnitine ≥97.0% (TLC)

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Supelco

91503

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Myristoyl-L-carnitine analytical standard

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Isovaleryl-L-carnitine ≥94.0% (HPLC)

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Lauroyl-L-carnitine analytical standard

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Butyryl-L-carnitine ≥97.0% (TLC)

Sigma-Aldrich

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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
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
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

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