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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
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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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)
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
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
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