Palmitoleic acid

Palmitoleic acid
IUPAC name
(9Z)-Hexadec-9-enoic acid
Other names
Palmitoleic acid
cis-Palmitoleic acid
9-cis-Hexadecenoic acid
C16:1 (Lipid numbers)
373-49-9 YesY
3D model (Jmol) Interactive image
ChemSpider 393216 N
ECHA InfoCard 100.006.151
PubChem 445638
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).
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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 breast milk,[2] 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.[3][4]


  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-10-120. PMC 3155149Freely accessible. PMID 21774832.
  2. Ogunleye A, Fakoya AT, Niizeki S, Tojo H, Sasajima I, Kobayashi M, Tateishi S, Yamaguchi K (1991). "Fatty acid composition of breast milk from Nigerian and Japanese women". J Nutr Sci Vitaminol (Tokyo). 1991 Aug;37(4):435-42. 37 (4): 435–42. doi:10.3177/jnsv.37.435. PMID 1765848.
  3. "Nuts, macadamia nuts, raw".
  4. 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.
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