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 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:28716;
ChemSpider	393216 ;
ECHA InfoCard	100.006.151
IUPHAR/BPS	5547;
PubChem CID	445638;
UNII	209B6YPZ4I ;
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- Key: SECPZKHBENQXJG-FPLPWBNLSA-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). verify (what is ?) 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. It is a rare component of fats. It 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.

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