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42602

Sigma-Aldrich

Propionyl-L-carnitine

≥94.0% (HPLC), suitable for LC/MS

Synonym(s):

(2R)-3-Carboxy-N,N,N-trimethyl-2-(1-oxopropoxy)-1-propanaminium inner salt, L-Carnitine propionyl ester, C3-Carnitine, Propanoyl-L-carnitine

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About This Item

Empirical Formula (Hill Notation):
C10H19NO4
CAS Number:
20064-19-1
Molecular Weight:
217.26
MDL number:
MFCD00870024
UNSPSC Code:
12352209
PubChem Substance ID:
329756246
NACRES:
NA.26

Product Name

Propionyl-L-carnitine, ≥94.0% (HPLC)

Quality Level

100

Assay

≥94.0% (HPLC)

form

powder or crystals

optical activity

[α]/D -23±3°, c = 1 in H2O

technique(s)

LC/MS: suitable

impurities

≤10% water (calcd. from elemental analysis)

color

white to off-white

storage temp.

2-8°C

SMILES string

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

InChI

1S/C10H19NO4/c1-5-10(14)15-8(6-9(12)13)7-11(2,3)4/h8H,5-7H2,1-4H3/t8-/m1/s1

InChI key

UFAHZIUFPNSHSL-MRVPVSSYSA-N

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General description

Propionyl-L-carnitine (PLC) is a short-chain fatty acid ester derivative of carnitine.

Application

Propionyl-L-carnitine has been used as a standard in liquid chromatography-tandem mass spectrometry (LC-MS/MS).

Biochem/physiol Actions

Propionyl-L-carnitine (PLC) plays a key role in lipid and carbohydrate metabolism. It provides substrates to the ischemic muscle for energy production and ATP generation. PLC has the potential to treat severe peripheral arterial disease and chronic heart failure. It is present in high abundance in the urine of patients with methylmalonyl-CoA mutase (MUT) deficiency, together with methylmalonic acid. MUT is a mitochondrial enzyme that catalyzes the isomerization of methylmalonyl-CoA to succinyl-CoA.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
BCCJ5697
BCCB9653
BCBZ8342
BCBX4946
BCBV0261

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William R Hiatt et al.
Journal of cardiopulmonary rehabilitation and prevention, 31(2), 125-132 (2010-09-24)
Exercise training is established for the treatment of peripheral artery disease; however the additional benefit of pharmacologic therapy with exercise has not been studied. This trial tested the hypothesis that propionyl-L-carnitine (PLC), in combination with monitored home-based exercise training, would
M J Cipolla et al.
Journal of vascular surgery, 29(6), 1097-1103 (1999-06-09)
The vasoactive effects of propionyl-L-carnitine (PLC) on human arteries, including endothelial and smooth muscle cell influences, were studied. Small (less than 200 microm) subcutaneous fat arteries (n = 19), obtained from human patients undergoing vascular surgery, were dissected and mounted
Carmen Mingorance et al.
Nutrition reviews, 69(5), 279-290 (2011-04-28)
Propionyl-L-carnitine (PLC) is a naturally occurring derivative of carnitine that plays an important role in the metabolism of both carbohydrates and lipids, leading to an increase of ATP generation. PLC, however, is not only a metabolic drug; it is also
Santica M Marcovina et al.
Translational research : the journal of laboratory and clinical medicine, 161(2), 73-84 (2012-11-10)
Mitochondria play important roles in human physiological processes, and therefore, their dysfunction can lead to a constellation of metabolic and nonmetabolic abnormalities such as a defect in mitochondrial gene expression, imbalance in fuel and energy homeostasis, impairment in oxidative phosphorylation
Qixiao Jiang et al.
Environmental toxicology and pharmacology, 48, 116-124 (2016-10-25)
Perfluorooctanoic acid (PFOA), a persistent organic pollutant, is associated with developmental toxicity. This study investigated the mechanism of PFOA-induced developmental cardiotoxicity in chicken embryo, focusing on the interactions between developmental exposure to PFOA and the levels of l-carnitine (LC), acetyl-l-carnitine
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