Palmitoleic acid

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.

Palmitoleic acid

Names
Preferred IUPAC name (9Z)-Hexadec-9-enoic acid
Other names Palmitoleic acid cis-Palmitoleic acid 9-cis-Hexadecenoic acid C16:1 (Lipid numbers)
Identifiers
CAS Number	373-49-9 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:28716
ChemSpider	393216 N
ECHA InfoCard	100.006.151
IUPHAR/BPS	5547
PubChem CID	445638
UNII	209B6YPZ4I Y
CompTox Dashboard (EPA)	DTXSID0041197
InChI InChI=1S/C16H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h7-8H,2-6,9-15H2,1H3,(H,17,18)/b8-7- N Key: SECPZKHBENQXJG-FPLPWBNLSA-N N InChI=1/C16H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h7-8H,2-6,9-15H2,1H3,(H,17,18)/b8-7- Key: SECPZKHBENQXJG-FPLPWBNLBE
SMILES O=C(O)CCCCCCC\C=C/CCCCCC
Properties
Chemical formula	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). N verify (what is YN ?) Infobox references

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]

Dietary sources

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]}