Palmitoleic acid

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Palmitoleic acid
Palmitoleic acid.svg
Identifiers
CAS number 373-49-9 YesY
PubChem 445638
ChemSpider 393216 N
Jmol-3D images Image 1
Properties
Molecular formula C16H30O2
Molar mass 254.408
Density 0.894 g/cm3
Melting point −0.1 °C (31.8 °F; 273.0 K)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references

Palmitoleic acid, or (Z)-9-hexadecenoic 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[edit]

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.

Potential biological effects[edit]

In an analysis of numerous fatty acids, palmitoleate was shown to possibly influence fatty liver deposition/production, insulin action, palmitate, and fatty acid synthase, leading to proposal of a new term, "lipokine," having hormone-like effects.[4]

As one such effect may include altered insulin sensitivity, palmitoleic acid (C16:1 n-7) was shown in diabetic mice to attenuate hyperglycemia and hypertriglyceridemia by increasing insulin sensitivity, in part owing to suppression of pro-inflammatory gene expressions and improving hepatic lipid metabolism.[5] Seemingly contrary results have been reported, but that study was measuring natural levels of phospholipid palmitoleate in plasma rather than the effect of adding palmitoleic acid to the diet; those with higher palmitoleate in plasma tended to have greater body mass index, and greater intakes of carbohydrate, protein, and alcohol.[6]

Other preliminary research indicated that palmitoleic acid could have a role as a signaling molecule affecting body weight,[7] a finding consistent with previous observations that palmitoleic acid, among other fatty acids available in the diet, may be used by enzymes affecting fat oxidation.[8] As a consequence, oil types manufactured with high palmitoleic acid content may have a role in addressing obesity.[9]

In the United States military, palmitoleic acid has been considered as a component in ready-to-eat meals (MRE).[citation needed] A study for the U.S. Army, initiated in 1996 by the University of Hawaii at Manoa, implied that the monounsaturated fatty acid not only may provide short-term benefits by energy needed in field and combat situations but also may ensure long-term fitness by minimizing risks of cardiovascular disease.[citation needed] Palmitoleic acid-rich products might be especially applicable for certain types of MRE rations.

The significance of palmitoleic acid in U.S. military nutrition research is also mentioned in a 2011 study.[citation needed] This preliminary research cites palmitoleic acid as a possible protective factor related to mental health and suicide, and states that service members with higher levels of palmitoleic acid may have lower risk of suicide.[citation needed]

References[edit]

  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. 
  4. ^ Hodson, L.; Karpe, F. (2013). "Is there something special about palmitoleate?". Current Opinion in Clinical Nutrition and Metabolic Care 16 (2): 225–231. doi:10.1097/MCO.0b013e32835d2edf. PMID 23324899.  edit
  5. ^ Chronic administration of palmitoleic acid reduces insulin resistance and hepatic lipid accumulation in KK-Ay Mice with genetic type 2 diabetes, Central Research Laboratory, Tokyo Innovation Center, Nippon Suisan Kaisha
  6. ^ Mozaffarian, D.; Cao, H.; King, I. B.; Lemaitre, R. N.; Song, X.; Siscovick, D. S.; Hotamisligil, G. S. (2010). "Circulating palmitoleic acid and risk of metabolic abnormalities and new-onset diabetes". American Journal of Clinical Nutrition 92 (6): 1350–1358. doi:10.3945/ajcn.110.003970. PMC 2980960. PMID 20943795.  edit
  7. ^ Zelkowitz R (2008-09-19). "Fat molecule fights weight gain". Science Now. 
  8. ^ Power, G.W., Cake, M.H. & Newsholme E.A. (1997) The influence of diet on the activity of carnitine palmitoyltransferase 1 toward a range of acyl CoA esters. Lipids 32: 31-37
  9. ^ "Fat and Slimy" 7.30 Report, Australian Broadcasting Commission November 1995