Palmitoleic acid

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Palmitoleic acid
Palmitoleic acid.svg
Preferred IUPAC name
(9Z)-Hexadec-9-enoic acid
Other names
Palmitoleic acid
cis-Palmitoleic acid
9-cis-Hexadecenoic acid
C16:1 (Lipid numbers)
3D model (JSmol)
ECHA InfoCard 100.006.151 Edit this at Wikidata
  • 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
  • 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-
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).
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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.[1] Many of the effects of palmitoleic acid are due to its activation of PPAR-alpha.[1]

Dietary sources[edit]

Palmitoleic acid can be abbreviated as 16:1∆9. Dietary sources of palmitoleic acid include breast milk,[2] 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.[3][4] It also comprises 13.55% of the fats from the fruit of the durian species Durio graveolens.[5]


  1. ^ a b de Souza CO, Vannice GK, Rosa Neto JC, Calder PC (2018). "Is Palmitoleic Acid a Plausible Nonpharmacological Strategy to Prevent or Control Chronic Metabolic and Inflammatory Disorders?" (PDF). Molecular Nutrition & Food Research. 62 (1): 1700504. doi:10.1002/mnfr.201700504. PMID 28980402.
  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). 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. Archived from the original on 2010-12-30.
  5. ^ Nasaruddin, Mohd hanif; Noor, Noor Qhairul Izzreen Mohd; Mamat, Hasmadi (2013). "Komposisi Proksimat dan Komponen Asid Lemak Durian Kuning (Durio graveolens) Sabah" [Proximate and Fatty Acid Composition of Sabah Yellow Durian (Durio graveolens)] (PDF). Sains Malaysiana (in Malay). 42 (9): 1283–1288. ISSN 0126-6039. OCLC 857479186. Retrieved 28 November 2017.