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.
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
- ^ 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.
- ^ 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.
- ^ 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.
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