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Propionyl-L-carnitine

Name: Propionyl-L-carnitine
Brand: SIGMA

≥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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Amino Acids

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.

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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Effect of propionyl-L-carnitine on a background of monitored exercise in patients with claudication secondary to peripheral artery disease.

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

Pharmacological effects and clinical applications of propionyl-L-carnitine.

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

Propionyl-L-carnitine dilates human subcutaneous arteries through an endothelium-dependent mechanism.

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

Translating the basic knowledge of mitochondrial functions to metabolic therapy: role of L-carnitine.

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

Changes in the levels of l-carnitine, acetyl-l-carnitine and propionyl-l-carnitine are involved in perfluorooctanoic acid induced developmental cardiotoxicity in chicken embryo.

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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