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P4509

Sigma-Aldrich

Palmitoyl-DL-carnitine chloride

powder

Synonym(s):

DL-Hexadecanoylcarnitine, Hexadecanoyl-DL-carnitine, NSC 628323, ​DL-Palmitoylcarnitine

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About This Item

Linear Formula:
C23H46NO4 · Cl
CAS Number:
6865-14-1
Molecular Weight:
436.07
MDL number:
MFCD00063481
UNSPSC Code:
12352200
PubChem Substance ID:
24278634
NACRES:
NA.77

biological source

synthetic (organic)

Assay

≥98% (TLC)

form

powder

color

white

solubility

H2O: 25 mg/mL (with heat or sonication)

storage temp.

−20°C

SMILES string

Cl.CCCCCCCCCCCCCCCC(=O)OC(CC(O)=O)C[N](C)(C)C

InChI

1S/C23H46NO4.ClH/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23(27)28-21(19-22(25)26)20-24(2,3)4;/h21H,5-20H2,1-4H3,(H,25,26);1H

InChI key

LGVBWSFTXDIBPB-UHFFFAOYSA-N

Application

Palmitoyl-DL-carnitine chloride has been used to study its effect on inflammatory cytokines and calcium (Ca2+) influx, using in vitro models of prostate cancer.

Biochem/physiol Actions

Long-chain acylcarnitine and well-known intermediate in mitochondrial fatty acid oxidation. Modifies myocardial levels of high-energy phosphates and free fatty acids in the heart. Increases erythroid colony formation in culture. Reduces surface negative charge of erythrocytes and myocytes. Reported to affect currents and inhibit endothelium-dependent relaxation induced by acetylcholine and substance P in a dose dependent manner by suppressing the intracellular calcium signal transduction in endothelial cells.
Palmitoyl-DL-carnitine chloride is known to inhibit biofilm formation mediated by Pseudomonas aeruginosa and Escherichia coli. It is a phosphokinase C inhibitor.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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Journal of Chemical and Pharmaceutical Sciences , 76(14), 29-29 (2012)
Accumulation of Palmitoylcarnitine and Its Effect on Pro-Inflammatory Pathways and Calcium Influx in Prostate Cancer
Al-Bakheit A, et al.
Prostate, 76(14), 1326-1337 (2016)
Signal transduction of the prophenoloxidase-activating system of prawn haemocytes triggered by CpG oligodeoxynucleotides
Chuo CP, et al.
Fish & Shellfish Immunology, 18(2), 149-162 (2005)
S R Stapleton et al.
British journal of pharmacology, 107(4), 1192-1197 (1992-12-01)
1. The effects of palmitoyl-DL-carnitine (0.01 to 1 mM) on whole cell voltage-activated calcium channel currents carried by calcium or barium and Ca(2+)-activated chloride currents were studied in cultured neurones from rat dorsal root ganglia. 2. Palmitoyl-DL-carnitine applied to the
Q Y Liu et al.
Biochemical and biophysical research communications, 228(2), 252-258 (1996-11-12)
We have studied the effect of a palmitoyl-L-carnitine (L-PC) on single cardiac L-type Ca channels incorporated from porcine ventricular sarcolemma into planar lipid bilayers where we could control the concentration, intracellular and/or extracellular location, and duration of L-PC treatment. We
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