Palmitoleic acid

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
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

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 that is a common constituent of the glycerides of human adipose tissue. 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. Many of the effects of palmitoleic acid are due to its activation of PPAR-alpha.

Dietary sources

Palmitoleic acid can be abbreviated as 16:1∆⁹. Dietary sources of palmitoleic acid include breast milk, 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.