Palmitoleic_acid Knowpia

Palmitoleic acid
Names
	Preferred IUPAC name (9Z)-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 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:28716;
ChemSpider	393216 ;
ECHA InfoCard	100.006.151
IUPHAR/BPS	5547;
PubChem CID	445638;
UNII	209B6YPZ4I ;
CompTox Dashboard (EPA)	DTXSID0041197 ;
	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;
	SMILES O=C(O)CCCCCCC\C=C/CCCCCC;
Properties
Chemical formula	C16H30O2
Molar mass	254.414 g·mol−1
Density	0.894 g/cm3
Melting point	−0.1 °C (31.8 °F; 273.0 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Palmitoleic acid, or (9Z)-hexadec-9-enoic acid, is an omega-7 monounsaturated fatty acid (16:1n-7) with the formula CH₃(CH₂)₅CH=CH(CH₂)₇COOH. It is a rare component of fats.^[1] It is a common constituent of the glycerides of human adipose tissue.^{[citation needed]} 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 Stearoyl-CoA desaturase-1.

Animal and cell culture studies indicate that palmitoleic acid is anti-inflammatory, and improves insulin sensitivity in liver and skeletal muscles, but more studies are required to establish its actions in humans.^[2] Many of the effects of palmitoleic acid are due to its activation of PPAR-alpha.^[2]

Dietary sources

Palmitoleic acid is found in trace amounts in most foods except for sardine oil, which contains 15% of this acid as a component of triglycerides.^[1]

Other dietary sources of palmitoleic acid include breast milk,^[3] a variety of animal fats, vegetable oils, and marine oils. Macadamia oil (Macadamia integrifolia) and sea buckthorn oil (Hippophae rhamnoides) are botanical sources with high concentrations, containing 17% and 19-29% palmitoleic acid, respectively.^{[citation needed]}^[4]^[5]

References

^ ^a ^b Anneken, David J.; Both, Sabine; Christoph, Ralf; Fieg, Georg; Steinberner, Udo; Westfechtel, Alfred (2006). "Fatty Acids". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a10_245.pub2. ISBN 9783527303854.
^ ^a ^b de Souza CO, Vannice GK, Rosa Neto JC, Calder PC (2018). "Is Palmitoleic Acid a Plausible Nonpharmacological Strategy to Prevent or Control Chronic Metabolic and Inflammatory Disorders?" (PDF). Molecular Nutrition & Food Research. 62 (1): 1700504. doi:10.1002/mnfr.201700504. PMID 28980402.
^ Ogunleye A, Fakoya AT, Niizeki S, Tojo H, Sasajima I, Kobayashi M, Tateishi S, Yamaguchi K (1991). "Fatty acid composition of breast milk from Nigerian and Japanese women". J Nutr Sci Vitaminol (Tokyo). 37 (4): 435–42. doi:10.3177/jnsv.37.435. PMID 1765848.
^ "Nuts, macadamia nuts, raw". NutritionData.com.
^ 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. Archived from the original on 2010-12-30.

[Ullmann-1] Anneken, David J.; Both, Sabine; Christoph, Ralf; Fieg, Georg; Steinberner, Udo; Westfechtel, Alfred (2006). "Fatty Acids". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a10_245.pub2. ISBN 9783527303854.

[pmid28980402-2] Souza CO, Vannice GK, Rosa Neto JC, Calder PC (2018). "Is Palmitoleic Acid a Plausible Nonpharmacological Strategy to Prevent or Control Chronic Metabolic and Inflammatory Disorders?" (PDF). Molecular Nutrition & Food Research. 62 (1): 1700504. doi:10.1002/mnfr.201700504. PMID 28980402.

[3] Ogunleye A, Fakoya AT, Niizeki S, Tojo H, Sasajima I, Kobayashi M, Tateishi S, Yamaguchi K (1991). "Fatty acid composition of breast milk from Nigerian and Japanese women". J Nutr Sci Vitaminol (Tokyo). 37 (4): 435–42. doi:10.3177/jnsv.37.435. PMID 1765848.

[4] "Nuts, macadamia nuts, raw". NutritionData.com.

[5] 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. Archived from the original on 2010-12-30.

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Names

Preferred IUPAC name (9Z)-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
3D model (JSmol)	Interactive image
ChEBI	CHEBI:28716
ChemSpider	393216^N
ECHA InfoCard	100.006.151
IUPHAR/BPS	5547
PubChem CID	445638
UNII	209B6YPZ4I^Y
CompTox Dashboard (EPA)	DTXSID0041197
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-^N Key: SECPZKHBENQXJG-FPLPWBNLSA-N^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
SMILES O=C(O)CCCCCCC\C=C/CCCCCC
Properties
Chemical formula	C₁₆H₃₀O₂
Molar mass	254.414 g·mol⁻¹
Density	0.894 g/cm³
Melting point	−0.1 °C (31.8 °F; 273.0 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

Summary

Dietary sources

References