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39953

Sigma-Aldrich

Lauroyl-L-carnitine

≥95.0% (HPLC)

Synonyme(s) :

(-)-Lauroylcarnitine, dodecanoylcarnitine, (2R)-3-Carboxy-N,N,N-trimethyl-2-[(1-oxododecyl)oxy]-1-propanaminium inner salt, L-Carnitine dodecanoyl ester, C12-Carnitine, Dodecanoyl-L-carnitine

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About This Item

Formule empirique (notation de Hill):
C19H37NO4
Numéro CAS:
25518-54-1
Poids moléculaire :
343.50
Numéro Beilstein :
4147610
Code UNSPSC :
12352211
ID de substance PubChem :
329755920
Nomenclature NACRES :
NA.26

Niveau de qualité

100

Pureté

≥95.0% (HPLC)

Forme

powder or crystals

Activité optique

[α]/D -20±2°, c = 1 in methanol

Conditionnement

pkg of 10 mg
pkg of 50 mg

Impuretés

≤10% water

Couleur

white to off-white

Groupe fonctionnel

ester

Température de stockage

2-8°C

Chaîne SMILES 

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

InChI

1S/C19H37NO4/c1-5-6-7-8-9-10-11-12-13-14-19(23)24-17(15-18(21)22)16-20(2,3)4/h17H,5-16H2,1-4H3/t17-/m1/s1

Clé InChI

FUJLYHJROOYKRA-QGZVFWFLSA-N

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Description générale

Lauroyl-L-carnitine, or Dodecanoylcarnitine, is an acylcarnitine compound with essential roles in energy metabolism. Synthesized in the liver from methionine, this metabolite of lysine is integral in various metabolic processes, making it a valuable asset in both biochemical and metabolomics research. Its concentration can serve as a diagnostic marker, particularly in cases of carnitine deficiency, and is of significance in assessing disease activity and diagnosing conditions like HIV and chronic hepatitis B infections. Additionally, Lauroyl-L-carnitine is associated with fatty acid oxidation disorders, including long-chain acyl CoA dehydrogenase deficiency and carnitine palmitoyltransferase I/II deficiency, further enhancing its relevance in metabolic research and diagnosis. This acylcarnitine compound has also been detected in cancer tissues, human serum, and tissue biopsies, expanding its applications and potential contributions to various areas of metabolomics research.

Application

Lauroyl-L-carnitine finds application in biochemical research and metabolomics research.

Actions biochimiques/physiologiques

Lauroyl-L-carnitine is an acylcarnitine is present in fatty acid oxidation disorders such as long-chain acyl CoA dehydrogenase deficiency, carnitine palmitoyltransferase I deficiency, and carnitine palmitoyltransferase II deficiency.

Caractéristiques et avantages

  • Can be used in Metabolomics and Biochemical research
  • High-quality compound suitable for multiple research applications

Autres remarques

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Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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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
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
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
Christoph Nowak et al.
Scientific reports, 8(1), 8691-8691 (2018-06-08)
Insulin resistance (IR) predisposes to type 2 diabetes and cardiovascular disease but its causes are incompletely understood. Metabolic challenges like the oral glucose tolerance test (OGTT) can reveal pathogenic mechanisms. We aimed to discover associations of IR with metabolite trajectories
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