Palmitic acid is a common 16-carbon saturated fat that represents 10-20% of the normal human dietary fat intake. Palmitic acid also makes up approximately 25% of the total plasma fatty acids in plasma lipoproteins.1 Saturated fatty acids induce the expression of cyclooxygenase-2 and, after protein acylation, are used to confer lipid anchoring to a variety of signaling molecules.2,3,4,5,6 Palmitic acid ethyl ester is a neutral, lipid-soluble form of the free acid. It is one of the fatty acid ethyl esters that increase cytosolic Ca2+ concentration leading to pancreatic acinar cell injury due to excessive consumption of ethanol.7
1
Santos, M.J., López-Jurado, M., Llopis, J., et al. Influence of dietary supplementation with fish oil on plasma fatty acid composition in coronary heart disease patients. Ann Nutr Metab3952-62(1995).
2
Dietzen, D.J., Hastings, W.R., and Lublin, D.M. Caveolin is palmitoylated on multiple cysteine residues. Palmitoylation is not necessary for localization of caveolin to caveolae. J Biol Chem2706838-6842(1995).
3
Robinson, L.J., and Michel, T. Mutagenesis of palmitoylation sites in endothelial nitric oxide synthase identifies a novel motif for dual acylation and subcellular targeting. Proc Natl Acad Sci USA9211776-11780(1995).
4
Topinka, J.R., and Bredt, D.S. N-terminal palmitoylation of PSD-95 regulates association with cell membranes and interaction with K+ channel Kv1.4. Neuron20125-134(1998).
5
Lee, J.Y., Sohn, K.H., Rhee, S.H., et al. Saturated fatty acids, but not unsaturated fatty acids, induced the expression of cyclooxygenase-2 mediated through toll-like receptor 4. J Biol Chem276(20)16683-16689(2001).
6
Miggin, S.M., Lawler, O.A., and Kinsella, B.T. Palmitoylation of the human prostacyclin receptor. Functional implications of palmitoylation and isoprenylation. J Biol Chem278(9)6947-6958(2003).
7
Chen, N., Appell, M., Berfield, J.L., et al. Inhibition by arachidonic acid and other fatty acids of dopamine uptake at the human dopamine transporter. Eur J Pharmacol47889-95(2003).
Synonyms
Ethyl palmitate
Ethyl hexadecanoate
Formal Name
hexadecanoic acid, ethyl ester
CAS Number
628-97-7
Molecular Formula
C18H36O2
Formula Weight
284.5
Formulation
A solution in ethanol
Purity
>98%
Stability
1 year
Storage
-20°C
Shipping
Wet ice
in continental US; may vary elsewhere
SMILES
Copy SMILES to clipboard
CCCCCCCCCCCCCCCC(=O)OCC
Background Reading
Santos, M.J., López-Jurado, M., Llopis, J., et al. Influence of dietary supplementation with fish oil on plasma fatty acid composition in coronary heart disease patients. Ann Nutr Metab3952-62(1995).
Robinson, L.J., and Michel, T. Mutagenesis of palmitoylation sites in endothelial nitric oxide synthase identifies a novel motif for dual acylation and subcellular targeting. Proc Natl Acad Sci USA9211776-11780(1995).
Miggin, S.M., Lawler, O.A., and Kinsella, B.T. Palmitoylation of the human prostacyclin receptor. Functional implications of palmitoylation and isoprenylation. J Biol Chem278(9)6947-6958(2003).
Chen, N., Appell, M., Berfield, J.L., et al. Inhibition by arachidonic acid and other fatty acids of dopamine uptake at the human dopamine transporter. Eur J Pharmacol47889-95(2003).
Topinka, J.R., and Bredt, D.S. N-terminal palmitoylation of PSD-95 regulates association with cell membranes and interaction with K+ channel Kv1.4. Neuron20125-134(1998).
Lee, J.Y., Sohn, K.H., Rhee, S.H., et al. Saturated fatty acids, but not unsaturated fatty acids, induced the expression of cyclooxygenase-2 mediated through toll-like receptor 4. J Biol Chem276(20)16683-16689(2001).
Dietzen, D.J., Hastings, W.R., and Lublin, D.M. Caveolin is palmitoylated on multiple cysteine residues. Palmitoylation is not necessary for localization of caveolin to caveolae. J Biol Chem2706838-6842(1995).