Palmitoleic acid

Last updated
Palmitoleic acid
Palmitoleic acid.svg
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
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.006.151 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • 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- X mark.svgN
    Key: SECPZKHBENQXJG-FPLPWBNLSA-N X mark.svgN
  • 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
  • O=C(O)CCCCCCC\C=C/CCCCCC
Properties
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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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. [1] It is a common constituent of the glycerides of human adipose tissue.[ citation needed ] 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. [2] Many of the effects of palmitoleic acid are due to its activation of PPAR-alpha. [2]

Natural sources

Palmitoleic acid is found in trace amounts in most foods except for sardine oil, which contains 15% of this acid as a component of triglycerides. [1]

Other dietary sources of palmitoleic acid include breast milk, [3] 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.[ citation needed ] [4] [5] .

Mink oil is also a source of palmitoleic acid.

References

  1. 1 2 Anneken, David J.; Both, Sabine; Christoph, Ralf; Fieg, Georg; Steinberner, Udo; Westfechtel, Alfred (2006). "Fatty Acids". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a10_245.pub2. ISBN   9783527303854.
  2. 1 2 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.{{cite journal}}: CS1 maint: article number as page number (link)
  3. ↑ 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.
  4. ↑ "Nuts, macadamia nuts, raw". NutritionData.com.
  5. ↑ 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.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.