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
ChemSpider	393216
IUPHAR/BPS	5547
Jmol interactive 3D	Image
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- 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	254.41 g·mol^−1
Density	0.894 g/cm^3
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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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.^[1]

Dietary sources

Palmitoleic acid can be abbreviated as 16:1∆⁹. Dietary sources of palmitoleic acid include 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%^[2] and 19% min to 29% max^[3] of palmitoleic acid, respectively.

References

1. Yang ZH, Miyahara H, Hatanaka A (2011). "Chronic administration of palmitoleic acid reduces insulin resistance and hepatic lipid accumulation in KK-Ay Mice with genetic type 2 diabetes". Lipids in Health and Disease 10: 120. doi:10.1186/1476-511X-10-12. PMC 3155149. PMID 21774832.
2. "Nuts, macadamia nuts, raw". NutritionData.com.
3. Li, Thomas S. C.; Thomas H. J. Beveridge (2003). Sea Buckthorn (Hippophae rhamnoides L.) : Production and Utilization. Ottawa, Ontario: NRC Research Press. pp. 54–55. ISBN 0-660-19007-9.