Palmitoleic acid (9-hexadecenoic acid) is an unsaturated fatty acid that is found in highest concentration in the liver. It is a common component of the glycerides of human adipose tissues. Two other sources of palmitoleic acid are macadamia oil and sea buckthorn oil which contain about 20% and 40% of total fatty acid composition, respectively.1,2 Palmitoleic acid ethyl ester (ethyl palmitoleate) is a more lipophilic 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. Ethyl palmitoleate (10-100 µM) in addition to 850 mM ethanol resulted in sustained, concentration-dependent increases in Ca2+ that caused cell death.3 This fatty acid ethyl ester is also a potential biomarker for fetal exposure to alcohol.4
1
Yang, B., and Kallio, H.P. Fatty acid composition of lipids in sea buckthorn (Hippophaë rhamnoids L.) berries of different origins. J Agric Food Chem491939-1947(2001).
2
Fard, A.M., Turner, A.G., and Willett, G.D. High-resolution electrospray-ionization fourier-transform ion cyclotron resonance and gas chromatography-mass spectrometry of macadamia nut oil. Aust J Chem56499-508(2003).
3
Criddle, D.N., Raraty, M.G.T., Neoptolemos, J.P., et al. Ethanol toxicity in pancreatic acinar cells: Mediation by nonoxidative fatty acid metabolites. Proc Natl Acad Sci USA101(29)10738-10743(2004).
4
Moore, C., Jones, J., Lewis, D., et al. Prevalence of fatty acid ethyl esters in meconium specimens. Clin Chem49(1)133-136(2003).
Synonyms
Ethyl Palmitoleate
Formal Name
9Z-hexadecenoic acid, ethyl ester
CAS Number
56219-10-4
Molecular Formula
C18H34O2
Formula Weight
282.5
Formulation
A solution in ethanol
Purity
>95%
Stability
1 year
Storage
-20°C
Shipping
Wet ice
in continental US; may vary elsewhere
SMILES
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CCCCCC/C=C\CCCCCCCC(OCC)=O
Background Reading
Yang, B., and Kallio, H.P. Fatty acid composition of lipids in sea buckthorn (Hippophaë rhamnoids L.) berries of different origins. J Agric Food Chem491939-1947(2001).
Fard, A.M., Turner, A.G., and Willett, G.D. High-resolution electrospray-ionization fourier-transform ion cyclotron resonance and gas chromatography-mass spectrometry of macadamia nut oil. Aust J Chem56499-508(2003).
Criddle, D.N., Raraty, M.G.T., Neoptolemos, J.P., et al. Ethanol toxicity in pancreatic acinar cells: Mediation by nonoxidative fatty acid metabolites. Proc Natl Acad Sci USA101(29)10738-10743(2004).
Moore, C., Jones, J., Lewis, D., et al. Prevalence of fatty acid ethyl esters in meconium specimens. Clin Chem49(1)133-136(2003).