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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)

Quality Level

200

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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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)
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)
Yige Fu et al.
Experimental cell research, 396(1), 112275-112275 (2020-09-09)
Limited treatment options and development of resistance to targeted therapy within few months pose significant challenges in the treatment of BRAF-mutated malignant melanoma. Moreover, extensive angiogenesis and vasculogenic mimicry promote the rapid progression of disease. The purpose of this study
T Nakadate et al.
Cancer research, 47(24 Pt 1), 6537-6542 (1987-12-15)
Palmitoylcarnitine, a reported protein kinase C inhibitor, enhanced the phorbol ester dependency of the enzyme, augmenting protein kinase C activity in the presence of phorbol esters such as phorbol 12,13-dibutyrate while inhibiting the basal activity measured in the presence of
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