Names | |
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Preferred IUPAC name
(9Z)-Hexadec-9-enoic acid | |
Other names | |
Identifiers | |
3D model (
JSmol)
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ChemSpider | |
ECHA InfoCard | 100.006.151 |
PubChem
CID
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UNII | |
CompTox Dashboard (
EPA)
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Properties | |
C16H30O2 | |
Molar mass | 254.414 g·mol−1 |
Density | 0.894 g/cm3 |
Melting point | −0.1 °C (31.8 °F; 273.0 K) |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
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Palmitoleic acid, or (9Z)-hexadec-9-enoic acid, is an omega-7 monounsaturated fatty acid (16:1n-7) with the formula CH3(CH2)5CH=CH(CH2)7COOH. It is a rare component of fats. [1] It is a common constituent of the glycerides of human adipose tissue.[ citation needed] It is present in all tissues but, in general, found in higher concentrations in the liver.
It is biosynthesized from palmitic acid by the action of the enzyme Stearoyl-CoA desaturase-1.
Animal and cell culture studies indicate that palmitoleic acid is anti-inflammatory, and improves insulin sensitivity in liver and skeletal muscles, but more studies are required to establish its actions in humans. [2] Many of the effects of palmitoleic acid are due to its activation of PPAR-alpha. [2]
Palmitoleic acid is found in trace amounts in most foods except for sardine oil, which contains 15% of this acid as a component of triglycerides. [1]
Other dietary sources of palmitoleic acid include breast milk, [3] a variety of animal fats, vegetable oils, and marine oils. Macadamia oil ( Macadamia integrifolia) and sea buckthorn oil ( Hippophae rhamnoides) are botanical sources with high concentrations, containing 17% and 19-29% palmitoleic acid, respectively.[ citation needed] [4] [5]