Palmitoleic acid

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Palmitoleic acid
Palmitoleic acid.svg
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
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.006.151 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • 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- X mark.svgN
    Key: SECPZKHBENQXJG-FPLPWBNLSA-N X mark.svgN
  • 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
  • O=C(O)CCCCCCC\C=C/CCCCCC
Properties
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).
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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 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]

Related Research Articles

<span class="mw-page-title-main">Fat</span> Esters of fatty acid or triglycerides

In nutrition, biology, and chemistry, fat usually means any ester of fatty acids, or a mixture of such compounds, most commonly those that occur in living beings or in food.

<span class="mw-page-title-main">Triglyceride</span> Any ester of glycerol having all three hydroxyl groups esterified with fatty acids

A triglyceride is an ester derived from glycerol and three fatty acids. Triglycerides are the main constituents of body fat in humans and other vertebrates as well as vegetable fat. They are also present in the blood to enable the bidirectional transference of adipose fat and blood glucose from the liver and are a major component of human skin oils.

Essential fatty acids, or EFAs, are fatty acids that are required by humans and other animals for normal physiological function that cannot be synthesized in the body.⁠ As they are not synthesized in the body, the essential fatty acids – alpha-linolenic acid (ALA) and linoleic acid – must be obtained from food or from a dietary supplement. Essential fatty acids are needed for various cellular metabolic processes and for the maintenance and function of tissues and organs. These fatty acids also are precursors to vitamins, cofactors, and derivatives, including prostaglandins, leukotrienes, thromboxanes, lipoxins, and others.

A saturated fat is a type of fat in which the fatty acid chains have all single bonds between the carbon atoms. A fat known as a glyceride is made of two kinds of smaller molecules: a short glycerol backbone and fatty acids that each contain a long linear or branched chain of carbon (C) atoms. Along the chain, some carbon atoms are linked by single bonds (-C-C-) and others are linked by double bonds (-C=C-). A double bond along the carbon chain can react with a pair of hydrogen atoms to change into a single -C-C- bond, with each H atom now bonded to one of the two C atoms. Glyceride fats without any carbon chain double bonds are called saturated because they are "saturated with" hydrogen atoms, having no double bonds available to react with more hydrogen.

An unsaturated fat is a fat or fatty acid in which there is at least one double bond within the fatty acid chain. A fatty acid chain is monounsaturated if it contains one double bond, and polyunsaturated if it contains more than one double bond.

<span class="mw-page-title-main">Palmitic acid</span> Chemical compound

Palmitic acid is a fatty acid with a 16-carbon chain. It is the most common saturated fatty acid found in animals, plants and microorganisms. Its chemical formula is CH3(CH2)14COOH, and its C:D ratio is 16:0. It is a major component of palm oil from the fruit of Elaeis guineensis, making up to 44% of total fats. Meats, cheeses, butter, and other dairy products also contain palmitic acid, amounting to 50–60% of total fats.

<span class="mw-page-title-main">Oleic acid</span> Monounsaturated omega-9 fatty acid

Oleic acid is a fatty acid that occurs naturally in various animal and vegetable fats and oils. It is an odorless, colorless oil, although commercial samples may be yellowish due to the presence of impurities. In chemical terms, oleic acid is classified as a monounsaturated omega-9 fatty acid, abbreviated with a lipid number of 18:1 cis-9, and a main product of Δ9-desaturase. It has the formula CH3−(CH2)7−CH=CH−(CH2)7−COOH. The name derives from the Latin word oleum, which means oil. It is the most common fatty acid in nature. The salts and esters of oleic acid are called oleates. It is a common component of oils, and thus occurs in many types of food, as well as in soap.

<span class="mw-page-title-main">Oily fish</span> Fish species with oils in their tissues and coelom

Oily fish are fish species with oil (fats) in soft tissues and in the coelomic cavity around the gut. Their fillets may contain up to 30% oil, although this figure varies both within and between species. Examples of oily fish include small forage fish such as sardines, herring and anchovies, and other larger pelagic fish such as salmon, trout, tuna, swordfish and mackerel.

Linoleic acid (LA) is an organic compound with the formula HOOC(CH2)7CH=CHCH2CH=CH(CH2)4CH3. Both alkene groups are cis. It is a fatty acid sometimes denoted 18:2 (n−6) or 18:2 cis-9,12. A linoleate is a salt or ester of this acid.

<i>Hippophae</i> Genus of flowering plants (sea buckthorns)

Hippophae is the genus of sea buckthorns, deciduous shrubs in the family Elaeagnaceae. The name sea buckthorn may be hyphenated to avoid confusion with the unrelated true buckthorns. It is also referred to as sandthorn, sallowthorn, or seaberry. It produces orange-yellow berries, which have been used over centuries as food, traditional medicine, and skin treatment in Mongolia, Ladakh, Russia, Ukraine, and northern Europe, which are its origin regions.

In biochemistry and nutrition, a monounsaturated fat is a fat that contains a monounsaturated fatty acid (MUFA), a subclass of fatty acid characterized by having a double bond in the fatty acid chain with all of the remaining carbon atoms being single-bonded. By contrast, polyunsaturated fatty acids (PUFAs) have more than one double bond.

<span class="mw-page-title-main">Mink oil</span> Oil derived from the fat of mink

Mink oil is an oil used in medical and cosmetic products. It is obtained by the rendering of mink fat which has been removed from pelts bound for the fur industry.

Capric acid, also known as decanoic acid or decylic acid, is a saturated fatty acid, medium-chain fatty acid (MCFA), and carboxylic acid. Its formula is CH3(CH2)8COOH. Salts and esters of decanoic acid are called caprates or decanoates. The term capric acid is derived from the Latin "caper / capra" (goat) because the sweaty, unpleasant smell of the compound is reminiscent of goats.

<i>Hippophae rhamnoides</i> Species of flowering plant

Hippophae rhamnoides, also known as sea-buckthorn, is a species of flowering plant in the family Elaeagnaceae, native to the cold-temperate regions of Europe and Asia. It is a spiny deciduous shrub. The plant is used in the food and cosmetics industries, in traditional medicine, as animal fodder, in horticulture, and for ecological purposes.

<span class="mw-page-title-main">Macadamia oil</span> Non-volatile oil expressed from the nut meat of the macadamia

Macadamia oil, also known as macadamia nut oil, is a non-volatile oil extracted from the nuts of the macadamia tree, indigenous to Australia. This oil is used in culinary applications as a frying or salad oil, and in cosmetics for its emollient properties and as a fragrance fixative.

Rose hip seed oil is a pressed seed oil, extracted from the seeds of the wild rose bush Rosa rubiginosa in the southern Andes. Rosehip seed oil can also be extracted from Rosa canina, a wild rose species native to Europe, northwest Africa, and western Asia. The fruits of the rosehip have been used in folk medicine for a long time. Rosehips have prophylactic and therapeutic actions against the common cold, infectious diseases, gastrointestinal disorders, urinary tract diseases, and inflammatory diseases.

<span class="mw-page-title-main">Sea buckthorn oil</span> Vegetable oil

Sea buckthorn oil is a red-orange oil derived from sea buckthorn plants. The most commonly used species for this purpose is Hippophae rhamnoides. Species belonging to this genus accumulate lipids in the mesocarp, so the oil can be extracted from either the seeds or the pulp.

Vaccenic acid is a naturally occurring trans fatty acid and an omega-7 fatty acid. It is the predominant kind of trans-fatty acid found in human milk, in the fat of ruminants, and in dairy products such as milk, butter, and yogurt. Trans fat in human milk may depend on trans fat content in food. Vaccenic acid was discovered in 1928 in animal fats and butter. Mammals convert it into rumenic acid, a conjugated linoleic acid, where it shows anticarcinogenic properties. Cows milk had highest trans-vaccenic acid content in the first few days of the cows being milked, indicating that it is stockpiled similarly to omega-3 fatty acids.

A lipokine is a lipid-controlling hormone. The term was coined by Hotamisligil Lab in 2008 to classify fatty acids which modulate lipid metabolism by what he called a "chaperone effect".

Omega−7 fatty acids are a class of unsaturated fatty acids in which the site of unsaturation is seven carbon atoms from the end of the carbon chain.

References

  1. 1 2 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. 1 2 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.
  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.