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Palmitoleic acid information


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 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 393216 ☒N
ECHA InfoCard 100.006.151 Edit this at Wikidata
IUPHAR/BPS
  • 5547
PubChem CID
  • 445638
UNII
  • 209B6YPZ4I checkY
CompTox Dashboard (EPA)
  • DTXSID0041197 Edit this at Wikidata
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 checkY☒N ?)
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]

  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.
  2. ^ 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.

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Palmitoleic acid

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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...

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List of unsaturated fatty acids

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(Z)-tetradec-9-enoic acid, numerical representation 14:1, n-5, molecular weight 226.36, melting point of −4.5 – −4 °C. CAS Registry Number 544-64-9. Palmitoleic acid has...

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Stearic acid

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stearic acid that oxidatively desaturates to oleic acid is 2.4 times higher than the fraction of palmitic acid analogously converted to palmitoleic acid. Also...

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Mink oil

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contain as much or more palmitoleic acid (17% and 19–29% respectively) than does mink oil (17%). Mink oil and its fatty acids are unique among animal-derived...

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Cocoa butter

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monounsaturated oleic acid in each triglyceride. The predominant triglycerides are POS, SOS, and POP, where P = palmitic, O = oleic, and S = stearic acid residues...

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a fatty acid is a carboxylic acid with an aliphatic chain, which is either saturated or unsaturated. Most naturally occurring fatty acids have an unbranched...

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Sapienic acid

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name from the root sapiens. The equivalent fatty acid in mouse sebum is palmitoleic acid. Sapienic acid salts, esters, anion, and conjugate base are known...

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Sea buckthorn oil

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65% combined of the monounsaturated fatty acid, palmitoleic acid, and the saturated fatty acid, palmitic acid. This results in a major difference between...

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Triglyceride

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fatty acids. Animals synthesize even-numbered fatty acids, but bacteria possess the ability to synthesise odd- and branched-chain fatty acids. As a result...

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acid. Almost invariably that fatty acid is oleic acid (18:1 n−9). Palmitoleic acid (16:1 n−7) and cis-vaccenic acid (18:1 n−7) occur in small amounts in...

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Hydnocarpus wightianus

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Pitaya

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myristic acid (negligible), palmitic acid (17%), stearic acid (5%), palmitoleic acid (about 1%), oleic acid (22%), cis-vaccenic acid (3%), linoleic acid (50%)...

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Tallow

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Monounsaturated fatty acids: Oleic acid (C18-1, ω-9): 47% Palmitoleic acid (C16:1): 3% Polyunsaturated fatty acids: Linoleic acid: 3% Linolenic acid: 1% Tallow is...

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Jojoba oil

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it is composed almost entirely (~97%) of mono-esters of long-chain fatty acids (wax ester) and alcohols (isopropyl jojobate), accompanied by only a tiny...

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Apricot oil

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chiefly composed of oleic acid and linoleic acid, both of which are unsaturated fats. Palmitic acid, Palmitoleic acid, and Stearic acid make minor contributions...

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Egg oil

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Macadamia

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and contain, as 17% of total fat, the monounsaturated fat, omega-7 palmitoleic acid. Macadamia allergy is a type of food allergy to macadamia nuts which...

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Crocodile oil

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those found in human skin oil indicated that the Palmitoleic acid (6%), oleic acid (39%), and linoleic acid (20%) in crocodile oil showed higher percentage...

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α-linolenic acid, which oxidises in air. The fatty acids in a typical linseed oil are of the following types: The triply unsaturated α-linolenic acid (51.9–55...

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Yolk

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prevalent fatty acids in egg yolk typically is: Unsaturated fatty acids: Oleic acid, 47% Linoleic acid, 16% Palmitoleic acid, 5% Linolenic acid, 2% Saturated...

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Pumpkin seed oil

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seed oil has an intense nutty taste and is rich in polyunsaturated fatty acids. Browned oil has a bitter taste. Pumpkin seed oil serves as a salad dressing...

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Kusum oil

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letting them dry. The oil contains oleic acid (2-3%), stearic acid (2-6%), gadoleic acid, and arachidic acid as well as cyanogenic compounds, which must...

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Vaccenic acid

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Oxidation of omega-7 unsaturated fatty acids on the skin surface, such as palmitoleic acid and vaccenic acid, may be the cause of the phenomenon commonly...

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Lard

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