Palmitoleic acid

Palmitoleic acid
Names

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 (Jmol)	Interactive image
ChemSpider	393216^N
ECHA InfoCard	100.006.151
IUPHAR/BPS	5547
PubChem	445638
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	254.41 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 (what is ^YN ?)
Infobox references

Palmitoleic acid, or (9Z)-hexadec-9-enoic acid, is an omega-7 monounsaturated fatty acid 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 delta-9 desaturase. A beneficial fatty acid, it has been shown to increase insulin sensitivity by suppressing inflammation, as well as inhibit the destruction of insulin-secreting pancreatic beta cells.

Palmitoleic acid can be abbreviated as 16:1∆⁹. Dietary sources of palmitoleic acid include breast milk, a variety of animal oils, 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% of palmitoleic acid, respectively.

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