Linoleic acid

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Linoleic acid
LAnumbering.png
Linoleic-acid-from-xtal-1979-3D-balls.png
Linoleic-acid-from-xtal-1979-3D-vdW.png
Names
Preferred IUPAC name
(9Z,12Z)-Octadeca-9,12-dienoic acid
Other names
cis,cis-9,12-Octadecadienoic acid
C18:2 (Lipid numbers)
Identifiers
3D model (JSmol)
3DMet
1727101
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.428 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 200-470-9
57557
KEGG
PubChem CID
UNII
  • InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10H,2-5,8,11-17H2,1H3,(H,19,20)/b7-6-,10-9- Yes check.svgY
    Key: OYHQOLUKZRVURQ-HZJYTTRNSA-N Yes check.svgY
  • InChI=1/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10H,2-5,8,11-17H2,1H3,(H,19,20)/b7-6-,10-9-
    Key: OYHQOLUKZRVURQ-HZJYTTRNBX
  • CCCCC/C=C\C/C=C\CCCCCCCC(=O)O
Properties
C18H32O2
Molar mass 280.452 g·mol−1
AppearanceColorless oil
Density 0.9 g/cm3 [1]
Melting point −12 °C (10 °F) [1]
−6.9 °C (19.6 °F) [2]
−5 °C (23 °F) [3]
Boiling point 229 °C (444 °F) at 16 mmHg [2]
230 °C (446 °F) at 21 mbar [3]
230 °C (446 °F) at 16 mmHg [1]
0.139 mg/L [3]
Vapor pressure 16 Torr at 229 °C[ citation needed ]
Acidity (pKa)4.77 at 25°C [4]
Hazards
NFPA 704 (fire diamond)
NFPA 704.svgHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
0
Flash point 112 °C (234 °F) [3]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Linoleic acid (LA) is an organic compound with the formula HOOC(CH2)7CH=CHCH2CH=CH(CH2)4CH3. Both alkene groups (−CH=CH−) 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. [5]

Linoleic acid is a polyunsaturated, omega−6 fatty acid. It is a colorless liquid that is virtually insoluble in water but soluble in many organic solvents. [2] It typically occurs in nature as a triglyceride (ester of glycerin) rather than as a free fatty acid. [6] It is one of two essential fatty acids for humans, who must obtain it through their diet, [7] and the most essential, because the body uses it as a base to make the others.

The word "linoleic" derives from Latin linum ' flax 'and oleum 'oil', reflecting the fact that it was first isolated from linseed oil.

History

In 1844, F. Sacc, working at the laboratory of Justus von Liebig, isolated linoleic acid from linseed oil. [8] [9] In 1886, K. Peters determined the existence of two double bonds. [10] Its essential role in human diet was discovered by G. O. Burr and others in 1930. [11] Its chemical structure was determined by T. P. Hilditch and others in 1939, and it was synthesized by R. A. Raphael and F. Sondheimer in 1950. [12]

In physiology

The consumption of linoleic acid is vital to proper health, as it is an essential fatty acid. [13]

Metabolism and eicosanoids

Linoleic Acid Metabolism.gif

Linoleic acid (LA: C
18 H
32 O
2; 18:2,n−6) is a precursor to arachidonic acid (AA: C
20H
32O
2; 20:4,n−6) with elongation and unsaturation. [13] AA is the precursor to some prostaglandins, [14] leukotrienes (LTA, LTB, LTC), thromboxane (TXA) [15] and the N-acylethanolamine (NAE) arachidonoylethanolamine (AEA: C
22H
37 NO
2; 20:4,n−6), [16] and other endocannabinoids and eicosanoids. [17]

The metabolism of LA to AA begins with the conversion of LA into gamma-linolenic acid (GLA), effected by Δ6 desaturase. [18] GLA is converted to dihomo-γ-linolenic acid (DGLA), the immediate precursor to AA.

LA is also converted by various lipoxygenases, cyclooxygenases, cytochrome P450 enzymes (the CYP monooxygenases), and non-enzymatic autoxidation mechanisms to mono-hydroxyl products viz., 13-Hydroxyoctadecadienoic acid, and 9-Hydroxyoctadecadienoic acid; these two hydroxy metabolites are enzymatically oxidized to their keto metabolites, 13-oxo-octadecadienoic acid and 9-oxo-octadecdienoic acid. Certain cytochrome P450 enzymes, the CYP epoxygenases, catalyze oxidation of LA to epoxide products viz., its 12,13-epoxide, vernolic acid, and its 9,10-epoxide, coronaric acid. These linoleic acid products are implicated in human physiology and pathology. [19]

Hydroperoxides derived from the metabolism of anandamide (AEA: C
22H
37 NO
2; 20:4,n−6), or its linoleoyl analogues, are by a lipoxygenase action found to be competitive inhibitors of brain and immune cell FAAH, the enzyme that breaks down AEA and other endocannabinoids, and the compound linoleoyl-ethanol-amide (C
20H
37NO
2; 18:2,n−6), an N-acylethanolamine,[ clarification needed ] - the ethanolamide of linoleic acid (LA: C
18H
32O
2; 18:2,n−6) and its metabolized incorporated ethanolamine (MEA: C
2H
7NO), [20] is the first natural inhibitor of FAAH, discovered. [21] [22]

Uses and reactions

Linoleic acid is a component of quick-drying oils, which are useful in oil paints and varnishes. These applications exploit the lability of the doubly allylic C−H groups (−CH=CH−CH2−CH=CH−) toward oxygen in air (autoxidation). Addition of oxygen leads to crosslinking and formation of a stable film. [23]

Reduction of the carboxylic acid group of linoleic acid yields linoleyl alcohol. [24]

Linoleic acid is a surfactant with a critical micelle concentration of 1.5 x 10−4 M @ pH 7.5.[ citation needed ]

Linoleic acid has become increasingly popular in the beauty products industry because of its beneficial properties on the skin. Research points to linoleic acid's anti-inflammatory, acne reductive, skin-lightening and moisture retentive properties when applied topically on the skin. [25] [26] [27] [28]

Linoleic acid is also used in some bar of soap products.

Dietary sources

It is abundant in safflower, and corn oil, and comprises over half their composition by weight. It is present in medium quantities in soybean oils, sesame, and almonds. [29] [30]

Name% LA†ref.
Salicornia oil 75% [31]
Safflower oil72–78% [32]
Evening Primrose oil 65–80% [33]
Melon seed oil50–70% [34]
Poppyseed oil 74% [35]
Grape seed oil 70% [36]
Prickly Pear seed oil50–78% [37]
Cardoon oil60% [38] [39]
Hemp oil 54.3% [40]
Wheat germ oil 56% [41] [42]
Cottonseed oil 54% [43] [44]
Corn oil 51.9% [45]
Walnut oil 50–72% [46] [47]
Soybean oil 50.9% [48]
Sesame oil 45% [49] [50]
Pumpkin seed oil 42–59% [51]
Rice bran oil 39%
Argan oil 37%
Pistachio oil 32.7%
Peach oil29% [52]
Almonds 24%
Canola oil17.8% [53]
Sunflower oil 20.5% [54]
Chicken fat 18–23% [55]
Peanut oil 19.6% [56]
Egg yolk 16%
Linseed oil (flax), cold pressed14.2% [57]
Lard 10%
Palm oil 10%
Olive oil 8.4% [58]
Tallow 3%
Cocoa butter 3%
Macadamia oil 2%
Butter 2%
Coconut oil 2%
 †average val, except the items where a range is given

Other occurrences

Cockroaches release oleic and linoleic acid upon death, which discourages other roaches from entering the area. This is similar to the mechanism found in ants and bees, which release oleic acid upon death. [59]

Health effects

Consumption of linoleic acid has been associated with lowering the risk of cardiovascular disease, diabetes and premature death. [60] [61] [62] There is high-quality evidence that increased intake of linoleic acid decreases total blood cholesterol and low-density lipoprotein. [63] Higher in vivo circulating and tissue levels of linoleic acid are associated with a lower risk of major cardiovascular events. [64] Clinical trials have shown that increased linoleic acid intake does not increase markers of inflammation or oxidative stress. [65] [66]

The American Heart Association advises people to replace saturated fat with linoleic acid to reduce CVD risk. [67]

See also

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.

Omega−3 fatty acids, also called omega−3 oils, ω−3 fatty acids or n−3 fatty acids, are polyunsaturated fatty acids (PUFAs) characterized by the presence of a double bond three atoms away from the terminal methyl group in their chemical structure. They are widely distributed in nature, being important constituents of animal lipid metabolism, and they play an important role in the human diet and in human physiology. The three types of omega−3 fatty acids involved in human physiology are α-linolenic acid (ALA), eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA). ALA can be found in plants, while DHA and EPA are found in algae and fish. Marine algae and phytoplankton are primary sources of omega−3 fatty acids. DHA and EPA accumulate in fish that eat these algae. Common sources of plant oils containing ALA include walnuts, edible seeds, and flaxseeds as well as hempseed oil, while sources of EPA and DHA include fish and fish oils, and algae oil.

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.

α-Linolenic acid Chemical compound

α-Linolenic acid, also known as alpha-linolenic acid (ALA), is an n−3, or omega-3, essential fatty acid. ALA is found in many seeds and oils, including flaxseed, walnuts, chia, hemp, and many common vegetable oils.

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.

<span class="mw-page-title-main">Hemp oil</span> Oil from hemp seeds

Hemp oil is oil obtained by pressing hemp seeds. Cold pressed, unrefined hemp oil is dark to clear light green in color, with a nutty flavor. The darker the color, the grassier the flavour. It should not be confused with hash oil, a tetrahydrocannabinol-containing oil made from the Cannabis flower.

<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">Omega-6 fatty acid</span> Fatty acids where the sixth bond is double

Omega−6 fatty acids are a family of polyunsaturated fatty acids that have in common a final carbon-carbon double bond in the n−6 position, that is, the sixth bond, counting from the methyl end.

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">Eicosapentaenoic acid</span> Chemical compound

Eicosapentaenoic acid (EPA; also icosapentaenoic acid) is an omega−3 fatty acid. In physiological literature, it is given the name 20:5(n−3). It also has the trivial name timnodonic acid. In chemical structure, EPA is a carboxylic acid with a 20-carbon chain and five cis double bonds; the first double bond is located at the third carbon from the omega end.

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

Docosahexaenoic acid (DHA) is an omega−3 fatty acid that is an important component of the human brain, cerebral cortex, skin, and retina. It is given the fatty acid notation 22:6(n−3). It can be synthesized from alpha-linolenic acid or obtained directly from maternal milk (breast milk), fatty fish, fish oil, or algae oil. The consumption of DHA (e.g., from fatty fish such as salmon, herring, mackerel and sardines) contributes to numerous physiological benefits, including cognition. As a component of neuronal membranes, the function of DHA is to support neuronal conduction and to allow the optimal functioning of neuronal membrane proteins (such as receptors and enzymes).

<span class="mw-page-title-main">Sunflower oil</span> Oil pressed from the seed of Helianthus annuus

Sunflower oil is the non-volatile oil pressed from the seeds of the sunflower. Sunflower oil is commonly used in food as a frying oil, and in cosmetic formulations as an emollient.

<span class="mw-page-title-main">Polyunsaturated fat</span> Type of fatty acid defined by molecular bonds

In biochemistry and nutrition, a polyunsaturated fat is a fat that contains a polyunsaturated fatty acid, which is a subclass of fatty acid characterized by a backbone with two or more carbon–carbon double bonds. Some polyunsaturated fatty acids are essentials. Polyunsaturated fatty acids are precursors to and are derived from polyunsaturated fats, which include drying oils.

Fatty acid desaturases are a family of enzymes that convert saturated fatty acids into unsaturated fatty acids and polyunsaturated fatty acids. For the common fatty acids of the C18 variety, desaturases convert stearic acid into oleic acid. Other desaturases convert oleic acid into linoleic acid, which is the precursor to alpha-linolenic acid, gamma-linolenic acid, and eicosatrienoic acid.

<span class="mw-page-title-main">Essential fatty acid interactions</span>

There is a wide variety of fatty acids found in nature. Two classes of fatty acids are considered essential, the omega-3 and omega-6 fatty acids. Essential fatty acids are necessary for humans but cannot be synthesized by the body and must therefore be obtained from food. Omega-3 and omega-6 are used in some cellular signaling pathways and are involved in mediating inflammation, protein synthesis, and metabolic pathways in the human body.

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.

α-Eleostearic acid Chemical compound

α-Eleostearic acid or (9Z,11E,13E)-octadeca-9,11,13-trienoic acid, is an organic compound, a conjugated fatty acid and one of the isomers of octadecatrienoic acid. It is often called simply eleostearic acid although there is also a β-eleostearic acid. Its high degree of unsaturation gives tung oil its properties as a drying oil.

Only two essential fatty acids are known to be essential for humans: alpha-linolenic acid and linoleic acid. The biological effects of the ω-3 and ω-6 fatty acids are mediated by their mutual interactions. Closely related, these fatty acids act as competing substrates for the same enzymes. The biological effects of the ω-3 and ω-6 fatty acids are largely mediated by essential fatty acid interactions. The proportion of omega-3 to omega-6 fatty acids in a diet may have metabolic consequences. Unlike omega-3 fatty acids and omega-6 fatty acids, omega-9 fatty acids are not classed as essential fatty acids because they can be created by the human body from monounsaturated and saturated fatty acids, and are therefore not essential in the diet.

<span class="mw-page-title-main">Cooking oil</span> Oil consumed by humans, of vegetable or animal origin

Cooking oil is a plant or animal liquid fat used in frying, baking, and other types of cooking. Oil allows higher cooking temperatures than water, making cooking faster and more flavorful, while likewise distributing heat, reducing burning and uneven cooking. It sometimes imparts its own flavor. Cooking oil is also used in food preparation and flavoring not involving heat, such as salad dressings and bread dips.

<span class="mw-page-title-main">Seed oil misinformation</span> Medical controversy

Since 2018, the health effects of consuming certain processed vegetable oils, or "seed oils" have been subject to misinformation in popular and social media. The trend grew in 2020 after podcaster and comedian Joe Rogan interviewed fad diet proponent Paul Saladino about the carnivore diet. Saladino made several claims about the health effects of vegetable fats.

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