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, ω-6) is a precursor to arachidonic acid (AA: C
20H
32O
2; 20:4, ω-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, ω-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%
Safflower oil72-78% [31]
Evening Primrose oil 65-80% [32]
Melon seed oil70%
Poppyseed oil 70%
Grape seed oil 69.6%
Prickly Pear seed oil63%
Artichoke oil 60%
Hemp oil 54.3% [33]
Wheat germ oil 55%
Cottonseed oil 54%
Corn oil 51.9% [34]
Walnut oil 51%
Soybean oil 50.9% [35]
Sesame oil 45%
Pumpkin seed oil 42-59% [36]
Rice bran oil 39%
Argan oil 37%
Pistachio oil 32.7%
Peach oil29% [37]
Almonds 24%
Canola oil17.8% [38]
Sunflower oil 20.5% [39]
Chicken fat 18-23% [40]
Peanut oil 19.6% [41]
Egg yolk 16%
Linseed oil (flax), cold pressed14.2% [42]
Lard 10%
Palm oil 10%
Olive oil 8.4% [43]
Cocoa butter 3%
Macadamia oil 2%
Butter 2%
Coconut oil 2%
 †average val

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. [44]

Health effects

Consumption of linoleic acid has been associated with lowering the risk of cardiovascular disease, diabetes and premature death. [45] [46] [47] There is high-quality evidence that increased intake of linoleic acid decreases total blood cholesterol and low-density lipoprotein. [48]

The American Heart Association advises people to replace saturated fat with linoleic acid to reduce CVD risk. [49]

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.

Essential fatty acids, or EFAs, are fatty acids that humans and other animals must ingest because the body requires them for good health, but cannot synthesize them.

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. 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">Linseed oil</span> Oil obtained from the dried, ripened seeds of the flax plant

Linseed oil, also known as flaxseed oil or flax oil, is a colourless to yellowish oil obtained from the dried, ripened seeds of the flax plant. The oil is obtained by pressing, sometimes followed by solvent extraction.

<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">Grape seed oil</span> Liquid fat derived from grape seeds

Grape seed oil is a vegetable oil derived from the seeds of grapes. A by-product of the winemaking industry, it is typically used for edible applications.

<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.

gamma-Linolenic acid or GLA is an n−6, or omega-6, fatty acid found primarily in seed oils. When acting on GLA, arachidonate 5-lipoxygenase produces no leukotrienes and the conversion by the enzyme of arachidonic acid to leukotrienes is inhibited.

<span class="mw-page-title-main">Rice bran oil</span> Oil extracted from the hard outer brown layer of rice

Rice bran oil is the oil extracted from the hard outer brown layer of rice called bran. It is known for its high smoke point of 232 °C (450 °F) and mild flavor, making it suitable for high-temperature cooking methods such as stir frying and deep frying. It is popular as a cooking oil in East Asia, the Indian subcontinent, and Southeast Asia including India, Nepal, Bangladesh, Indonesia, Japan, Southern China and Malaysia.

<span class="mw-page-title-main">Corn oil</span> Oil from the seeds of corn

Corn oil or maize oil (British) is oil extracted from the germ of corn (maize). Its main use is in cooking, where its high smoke point makes refined corn oil a valuable frying oil. It is also a key ingredient in some margarines. Corn oil is generally less expensive than most other types of vegetable oils.

<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 linolenic 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 are many fatty acids found in nature. Two types of fatty acids considered essential for human health are the omega-3 and omega-6 types. These two essential fatty acids are necessary for some cellular signalling pathways and are involved in mediating inflammation, protein synthesis, and metabolic pathways in the human body.

<span class="mw-page-title-main">Avocado oil</span> Edible oil pressed from the pulp of avocados

Avocado oil is an edible oil extracted from the pulp of avocados, the fruit of Persea americana. It is used as an edible oil both raw and for cooking, where it is noted for its high smoke point. It is also used for lubrication and in cosmetics.

Protein combining or protein complementing is a dietary theory for protein nutrition that purports to optimize the biological value of protein intake. According to the theory, vegetarian and vegan diets may provide an insufficient amount of some essential amino acids, making protein combining with multiple foods necessary to obtain a complete protein food. The terms complete and incomplete are outdated in relation to plant protein. In fact, all plant foods contain all 20 amino acids including the 9 essential amino acids in varying amounts.

<span class="mw-page-title-main">Linoleoyl-CoA desaturase</span> Class of enzymes

Linoleoyl-CoA desaturase (also Delta 6 desaturase, EC 1.14.19.3) is an enzyme that converts between types of fatty acids, which are essential nutrients in the human body. The enzyme mainly catalyzes the chemical reaction

<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.

References

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  18. ↑ Evidence suggests that infants must acquire Δ6-desaturase breast milk. Breast-milk fed babies have higher concentrations of GLA than formula-fed babies, while formula-fed babies have elevated concentrations of LA. David F. Horrobin (1993). "Fatty acid metabolism in health and disease: the role of Δ-6-desaturase". American Journal of Clinical Nutrition. 57 (5 Suppl): 732S–737S. doi: 10.1093/ajcn/57.5.732S . PMID   8386433.
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  46. ↑ Marangoni, Franca; Agostoni, Carlo; Borghi, Claudio; Catapano, Alberico L.; Cena, Hellas; Ghiselli, Andrea; La Vecchia, Carlo; Lercker, Giovanni; Manzato, Enzo; Pirillo, Angela; Riccardi, Gabriele; Risé, Patrizia; Visioli, Francesco; Poli, Andrea (2020). "Dietary linoleic acid and human health: Focus on cardiovascular and cardiometabolic effects". Atherosclerosis. 292: 90–98. doi:10.1016/j.atherosclerosis.2019.11.018. PMID   31785494. S2CID   208516015.
  47. ↑ Mousavi, Seyed Mohammad; Jalilpiran, Yahya; Karimi, Elmira; Aune, Dagfinn; Larijani, Bagher; Mozaffarian, Dariush; Willett, Walter C.; Esmaillzadeh, Ahmad (2021). "Dietary Intake of Linoleic Acid, Its Concentrations, and the Risk of Type 2 Diabetes: A Systematic Review and Dose-Response Meta-analysis of Prospective Cohort Studies". Diabetes Care. 44 (9): 2173–2181. doi: 10.2337/dc21-0438 . PMID   34417277. S2CID   237255109.
  48. ↑ "Systematic review of the evidence for relationships between saturated, cis monounsaturated, cis polyunsaturated fatty acids and selected individual fatty acids, and blood cholesterol concentration". foodstandards.gov.au. Retrieved 10 January 2023.
  49. ↑ Sacks FM, Lichtenstein AH, Wu JH, Appel LJ, Creager MA, Kris-Etherton PM, Miller M, Rimm EB, Rudel LL, Robinson JG, Stone NJ, Van Horn LV (July 2017). "Dietary Fats and Cardiovascular Disease: A Presidential Advisory From the American Heart Association". Circulation. 136 (3): e1–e23. doi: 10.1161/CIR.0000000000000510 . PMID   28620111. S2CID   367602.

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