Palmitoleic acid
| Palmitoleic acid | |
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hexadec-9-enoic acid |
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Other names
Palmitoleic acid |
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| Identifiers | |
| CAS number | 373-49-9  |
| PubChem | 4668 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C16H30O2 |
| Molar mass | 254.408 |
| Density | 0.894 g/cm³ |
| Melting point |
-0.1 °C |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| 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 generally 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 caused by saturated fats.[1]
[edit] 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 40%[3] of palmitoleic acid, respectively.
[edit] Potential biological effects
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 improved 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]
Other preliminary research indicated that palmitoleic acid could have a role as a signaling molecule affecting body weight,[6] 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.[7] Consequently, oil types manufactured with high palmitoleic acid content may have a role in addressing obesity.[8]
[edit] References
- ^ Chronic administration of palmitoleic acid reduces insulin resistance and hepatic lipid accumulation in KK-Ay Mice with genetic type 2 diabetes
- ^ "Nuts, macadamia nuts, raw". http://www.nutritiondata.com/facts/nut-and-seed-products/3123/2.
- ^ 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. http://www.ovid.com/site/catalog/Book/2738.jsp?top=2&mid=3&bottom=7&subsection=11.
- ^ Identification of a Lipokine, a Lipid Hormone Linking Adipose Tissue to Systemic Metabolism, Department of Genetics and Complex Diseases, Harvard School of Public Health
- ^ 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
- ^ Zelkowitz R (2008-09-19). "Fat molecule fights weight gain". http://sciencenow.sciencemag.org/cgi/content/full/2008/919/3?etoc.
- ^ 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
- ^ "Fat and Slimy" 7.30 Report, Australian Broadcasting Commission November 1995
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