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Saturated fatty acids are synthesized by both plants and animals from acetyl coenzyme A as a form of long-term energy storage. Palmitic acid is a common 16-carbon saturated fat that represents 10-20% of the normal dietary fat intake. Palmitic acid also makes up approximately 25% of the total plasma fatty acids in plasma lipoproteins.1 Saturated free fatty acids induce the expression of cyclooxygenase 2,2 and after protein acylation, are used to confer lipid anchoring to a variety of signaling molecules.3,4,5,6 Palmitate is the salt (in this case calcium) of palmitic acid. It is this anion that is observed at physiological pH. Calcium palmitate is one of the major components of gallstones.
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
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).
3
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).
4
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).
5
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).
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).
Synonyms
Calcium palmitate
Formal Name
Hexadecanoic acid, calcium salt
CAS Number
542-42-7
Molecular Formula
[C16H31O2]2 · Ca2+
Formula Weight
510.8
Formulation
A crystalline solid
Purity
>98%
Stability
2 years
Storage
-20°C
Shipping
Wet ice
in continental US; may vary elsewhere
SMILES
Copy SMILES to clipboard
CCCCCCCCCCCCCCCC(=O)O
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).
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).
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).
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).
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).
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).