Palmitoleic acid

Palmitoleic acid
IUPAC name hexadec-9-enoic acid
Other names Palmitoleic acid cis-Palmitoleic acid 9-cis-Hexadecenoic acid C16:1 (Lipid numbers)
Identifiers
CAS number	373-49-9 Y
PubChem	445638
ChemSpider	393216
Jmol-3D images	Image 1
SMILES O=C(O)CCCCCCC\C=C/CCCCCC
InChI 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- Key: SECPZKHBENQXJG-FPLPWBNLSA-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- Key: SECPZKHBENQXJG-FPLPWBNLBE
Properties
Molecular formula	C16H30O2
Molar mass	254.408
Density	0.894 g/cm³
Melting point	-0.1 °C
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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]

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 19% min to 29% max^[3] of palmitoleic acid, respectively.

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 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] Contrary results have been reported, indicating association with lower insulin resistance, presence of atherogenic dyslipidemia, and development of diabetes.^[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