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Palmitoleic acid



Palmitoleic acid
IUPAC name hexadec-9-enoic acid
Other names Palmitoleic acid
cis-Palmitoleic acid
9-cis-Hexadecenoic acid
Identifiers
CAS number 373-49-9
PubChem 4668
SMILES CCCCCCC=CCCCCCCCC(=O)O
Properties
Molecular formula C16H30O2
Molar mass 254.408
Density 0.894 g/cm³
Melting point

-0.1 °C

Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

Palmitoleic acid, or (Z)-9-hexadecenoic acid, is a omega-7 monounsaturated fatty acid 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.

Additional recommended knowledge

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 22[citation needed] and 40%[1] of palmitoleic acid, respectively.

In a recent study examining the effects of diets high in various fatty acids, total cholesterol and low density lipoprotein (LDL, "bad cholesterol") concentrations were similar with palmitoleic and palmitic acids and significantly higher than with oleic acid.[2] High density lipoprotein (HDL, "good cholesterol") was significantly lower with palmitoleic than with palmitic acid. The study confirms that, at least in hypercholesterolemic men, a modest increase in palmitic acid raises LDL cholesterol relative to oleic acid, even when dietary cholesterol is low. Palmitoleic acid behaves like a saturated and not a monounsaturated fatty acid in its effect on LDL cholesterol.

In the April 2001 issue of the Journal of Investigative Dermatology, Shinichiro Haze et al published an article suggesting that omega-7 unsaturated fatty acids, such as palmitoleic acid and vaccenic acid found on the skin surface were oxidatively decomposed to 2-nonenal, which may be the cause of the phenomenon commonly known as old person smell.[3]

References

  1. ^ Li, Thomas S. C.; Thomas H. J. Beveridge (2003). Sea Buckthorn (Hippophae rhamnoides L.) : Production and Utilization. Ottawa, Ontario: NRC Research Press, 54-55. ISBN 0-660-19007-9. 
  2. ^ Nestel P, Clifton P, Noakes M. (1994). "Effects of increasing dietary palmitoleic acid compared with palmitic and oleic acids on plasma lipids of hypercholesterolemic men". Journal of Lipid Research 35 (4): 656-662. PMID 8006520.
  3. ^ S. Haze, Y. Gozu, S. Nakamura, Y. Kohno, K. Sawano, H. Ohta and K. Yamazaki (2001). "2-Nonenal Newly Found in Human Body Odor Tends to Increase with Aging". Journal of Investigative Dermatology 116 (4): 520-524. doi:10.1046/j.0022-202x.2001.01287.x.
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Palmitoleic_acid". A list of authors is available in Wikipedia.
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