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Structure Database (LMSD)

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Common Name

SFE 2:0/16:0

Systematic Name

ethyl hexadecanoate

Synonyms

WE(2:0/16:0)
Ethyl palmitate

LM ID

LMFA07010471

Formula

C₁₈H₃₆O₂

Exact Mass

Calculate m/z

284.271531

Sum Composition

SFE 18:0

Status

Curated

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Classification

Biological Context

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

This information has been provided by Cayman Chemical

References

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. Metab. 39(1), 52-62 (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. The Journal of Biological Chemisty 270(12), 6838-6842 (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. USA 92(25), 11776-11780 (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. Neuron 20(1), 125-134 (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. The Journal of Biological Chemisty 276(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. The Journal of Biological Chemisty 278(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. Pharmacol. 478(2-3), 89-95 (2003).