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]

The American Heart Association advises people to replace saturated fat with linoleic acid to reduce CVD risk. [64]

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">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. Grape seeds are a winemaking by-product, and oil made from the seeds is commonly used as an edible oil.

<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.

γ-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">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.

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

Stearidonic acid (SDA: C18H28O2; 18:4, n-3) is an ω-3 fatty acid, sometimes called moroctic acid.

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.

<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

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.

References

  1. 1 2 3 The Merck Index , 11th Edition, 5382
  2. 1 2 3 William M. Haynes (2016). CRC Handbook of Chemistry and Physics (97th ed.). Boca Raton: CRC Press. pp. 3–338. ISBN   978-1-4987-5429-3.
  3. 1 2 3 4 Record of CAS RN 60-33-3 in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  4. ↑ National Center for Biotechnology Information (2024). PubChem Compound Summary for CID 5280450, Linoleic Acid. Retrieved January 20, 2024 from https://pubchem.ncbi.nlm.nih.gov/compound/Linoleic-Acid.
  5. ↑ "Fatty Acids". Cyber Lipid. Archived from the original on 28 October 2018. Retrieved 31 July 2017.
  6. ↑ Mattes, Richard D. (2009). "Is there a fatty acid taste?". Annual Review of Nutrition . 29: 305–327. doi:10.1146/annurev-nutr-080508-141108. PMC   2843518 . PMID   19400700.
  7. ↑ Simopoulos, Artemis P. (2008). "The importance of the omega-6/omega-3 fatty acid ratio in cardiovascular disease and other chronic diseases". Experimental Biology and Medicine. 233 (6): 674–688. doi:10.3181/0711-mr-311. PMID   18408140. S2CID   9044197.
  8. ↑ F. Sacc (1844). "Ueber das Leinöl, seine physicalischen und chemischen Eigenschaften und seine Oxydationsproducte". Liebigs Annalen , volume 51, issue 2, pages 213–230. doi : 10.1002/jlac.18440510207.
  9. ↑ F. Sacc (1845). "Expériences sur les propriétés physiques et chimiques de l'huile de Lin". Neue Denkschriften der Allg. Schweizerischen Gesellschaft für die Gesammten Naturwissenschaften, volume 7, pages 191–208 in pdf.
  10. ↑ Peters, Karl (December 1886). "Über Leinölsäure". Monatshefte für Chemie und verwandte Teile anderer Wissenschaften. 7: 552–555. doi:10.1007/BF01516597.
  11. ↑ Burr GO, Burr MM (April 1930). "On the Nature and Rôle of the Fatty Acids Essential in Nutrition". J. Biol. Chem. 86 (2): 587–621. doi: 10.1016/S0021-9258(20)78929-5 .
  12. ↑ Raphael, R.A.; Sondheimer, Franz (1950). "The synthesis of long-chain aliphatic acids from acetylenic compounds. Part III. The synthesis of linoleic acid". Journal of the Chemical Society (Resumed): article 432, pp 2100–2103. doi:10.1039/jr9500002100.
  13. 1 2 Whelan, Jay; Fritsche, Kevin (May 2013). "Linoleic Acid". Advances in Nutrition. 4 (3): 311–312. doi:10.3945/an.113.003772. PMC   3650500 . PMID   23674797.
  14. ↑ Wlodawer, Paulina; Samuelsson, Bengt (25 August 1973). "On the organization and mechanism of prostaglandin synthetase". The Journal of Biological Chemistry. 248 (16): 5673–5678. doi: 10.1016/S0021-9258(19)43558-8 . PMID   4723909.
  15. ↑ Terano, Takashi; Salmon, John A.; Moncada, Salvador (February 1984). "Biosynthesis and biological activity of leukotriene B5". Prostaglandins. 27 (2): 217–232. doi:10.1016/0090-6980(84)90075-3. PMID   6326200.
  16. ↑ Murru, Elisabetta; Lopes, Paula A.; Carta, Gianfranca; Manca, Claudia; Abolghasemi, Armita; Guil-Guerrero, José L.; Prates, José A. M.; Banni, Sebastiano (15 February 2021). "Different Dietary N-3 Polyunsaturated Fatty Acid Formulations Distinctively Modify Tissue Fatty Acid and N-Acylethanolamine Profiles". Nutrients. 13 (2): 625. doi: 10.3390/nu13020625 . ISSN   2072-6643. PMC   7919039 . PMID   33671938.
  17. ↑ Salem, Norman; Van Dael, Peter (27 February 2020). "Arachidonic Acid in Human Milk". Nutrients. 12 (3): 626. doi: 10.3390/nu12030626 . ISSN   2072-6643. PMC   7146261 . PMID   32121018.
  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.
  19. ↑ Jandacek, Ronald J. (20 May 2017). "Linoleic Acid: A Nutritional Quandary". Healthcare. 5 (2): 25. doi: 10.3390/healthcare5020025 . ISSN   2227-9032. PMC   5492028 . PMID   28531128.
  20. ↑ PubChem. "Linoleoyl ethanolamide". pubchem.ncbi.nlm.nih.gov. Retrieved 29 October 2022.
  21. ↑ Maccarrone, Mauro; Stelt, Marcelis van der; Rossi, Antonello; Veldink, Gerrit A.; Vliegenthart, Johannes F. G.; Agrò, Alessandro Finazzi (27 November 1998). "Anandamide Hydrolysis by Human Cells in Culture and Brain *". Journal of Biological Chemistry. 273 (48): 32332–32339. doi: 10.1074/jbc.273.48.32332 . hdl: 1887/50863 . ISSN   0021-9258. PMID   9822713.
  22. ↑ Scala, Coralie Di; Fantini, Jacques; Yahi, Nouara; Barrantes, Francisco J.; Chahinian, Henri (22 May 2018). "Anandamide Revisited: How Cholesterol and Ceramides Control Receptor-Dependent and Receptor-Independent Signal Transmission Pathways of a Lipid Neurotransmitter". Biomolecules. 8 (2): 31. doi: 10.3390/biom8020031 . ISSN   2218-273X. PMC   6022874 . PMID   29789479.
  23. ↑ Ulrich Poth (2002). "Drying Oils and Related Products". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a09_055. ISBN   978-3527306732.
  24. ↑ Adkins, Homer; Gillespie, R.H. (1949). "Oleyl Alcohol". Organic Syntheses. 29: 80. doi:10.15227/orgsyn.029.0080.
  25. ↑ Diezel, W.E.; Schulz, E.; Skanks, M.; Heise, H. (1993). "Plant oils: Topical application and anti-inflammatory effects (croton oil test)". Dermatologische Monatsschrift. 179: 173.
  26. ↑ Letawe, C.; Boone, M.; Pierard, G.E. (March 1998). "Digital image analysis of the effect of topically applied linoleic acid on acne microcomedones". Clinical and Experimental Dermatology. 23 (2): 56–58. doi:10.1046/j.1365-2230.1998.00315.x. PMID   9692305. S2CID   28594076.
  27. ↑ Ando, Hideya; Ryu, Atsuko; Hashimoto, Akira; Oka, Masahiro; Ichihashi, Masamitsu (March 1998). "Linoleic acid and α-linolenic acid lightens ultraviolet-induced hyperpigmentation of the skin". Archives of Dermatological Research. 290 (7): 375–381. doi:10.1007/s004030050320. PMID   9749992. S2CID   23036319.
  28. ↑ Darmstadt, Gary L.; Mao-Qiang, M.; Chi, E.; Saha, S.K.; Ziboh, V.A.; Black, R.E.; Santosham, M.; Elias, P.M. (2002). "Impact of topical oils on the skin barrier: possible implications for neonatal health in developing countries". Acta Paediatrica. 91 (5): 546–554. CiteSeerX   10.1.1.475.1064 . doi:10.1080/080352502753711678. PMID   12113324.
  29. ↑ "Nutrient Data Laboratory Home Page". USDA National Nutrient Database for Standard Reference, Release 20. U.S. Department of Agriculture, Agricultural Research Service. 2007. Archived from the original on 14 April 2016.
  30. ↑ Kaur, Narinder; Chugh, Vishal; Gupta, Anil K. (October 2014). "Essential fatty acids as functional components of foods- a review". Journal of Food Science and Technology. 51 (10): 2289–2303. doi:10.1007/s13197-012-0677-0. PMC   4190204 . PMID   25328170.
  31. ↑ Alfheeaid, Hani A.; et al. (November 2022). "Salicornia bigelovii, S. brachiata and S. herbacea: Their Nutritional Characteristics and an Evaluation of Their Potential as Salt Substitutes". Foods. 11 (21): 3402. doi: 10.3390/foods11213402 . PMC   9655280 . PMID   36360016.
  32. ↑ Hall III, C. (2015). Wrigley, Colin W.; Corke, Harold; Seetharaman, Koushik; Faubion, Jonathan (eds.). Encyclopedia of Food Grains. Academic Press. ISBN   978-0-12-394786-4.
  33. ↑ "Evening Primrose Oil for Menopause does it help". 26 January 2018.
  34. ↑ Zhang G, Li Z, Guo Z, Charalampopoulos D (June 2024). "Comparative extraction of melon seed (Cucumis melo L.) oil by conventional and enzymatic methods: Physicochemical properties and oxidative stability". Journal of Agriculture and Food Research. 16. doi: 10.1016/j.jafr.2024.101182 .
  35. ↑ Bozan, Berrin; Temelli, Feral (September 2008). "Chemical composition and oxidative stability of flax, safflower and poppy seed and seed oils". Bioresource Technology. 99 (14): 6354–6359. Bibcode:2008BiTec..99.6354B. doi:10.1016/j.biortech.2007.12.009. PMID   18198133.
  36. ↑ Martin ME, Grao-Cruces E, Millan-Linares MC, Montserrat-de la Paz S (October 2020). "Grape (Vitis vinifera L.) Seed Oil: A Functional Food from the Winemaking Industry". Foods. 9 (10): 1360. doi: 10.3390/foods9101360 . PMC   7599587 . PMID   32992712.
  37. ↑ Al-Naqeb G, Fiori L, Ciolli M, Aprea E (August 2021). "Prickly Pear Seed Oil Extraction, Chemical Characterization and Potential Health Benefits". Molecules. 26 (16): 5018. doi: 10.3390/molecules26165018 . PMC   8401162 . PMID   34443606.
  38. ↑ Varvouni EF, Graikou K, Gortzi O, Cheilari A, Aligiannis N, Chinou I (November 2021). "Chemical and Biological Evaluation of the Oil and Seedcake from Seeds of a Greek Cardoon Cultivar as Potential Functional Vegetable Oil. Comparison with Sesame, Flaxseed and Extra Virgin Olive Oils". Foods. 10 (11): 2665. doi: 10.3390/foods10112665 . PMC   8618587 . PMID   34828945.
  39. ↑ Barbosa CH, Andrade MA, Vilarinho F, Castanheira I, Fernando AL, Loizzo MR, Sanches Silva A (May 2020). "A New Insight on Cardoon: Exploring New Uses besides Cheese Making with a View to Zero Waste". Foods. 9 (5): 564. doi: 10.3390/foods9050564 . hdl: 10316/106089 . PMC   7278730 . PMID   32370268.
  40. ↑ Oomah, B. Dave; Busson, Muriel; Godfrey, David V; Drover, John C. G. (1 January 2002). "Characteristics of hemp (Cannabis sativa L.) seed oil". Food Chemistry. 76 (1): 33–43. doi:10.1016/S0308-8146(01)00245-X.
  41. ↑ Rahim MA, et al. (October 2023). "Essential Components from Plant Source Oils: A Review on Extraction, Detection, Identification, and Quantification". Molecules. 28 (19): 6881. doi: 10.3390/molecules28196881 . PMC   10574037 . PMID   37836725.
  42. ↑ Siraj, Naila (March 2022). "Wheat germ oil: a comprehensive review". Food Science and Technology. 42. doi: 10.1590/fst.113721 .
  43. ↑ Lukonge E, Labuschagne MT, Hugo A (January 2007). "The evaluation of oil and fatty acid composition in seed of cotton accessions from various countries". J Sci Food Agric. 87 (2): 340–347. Bibcode:2007JSFA...87..340L. doi:10.1002/jsfa.2731. To download the article, click the title (not doi) and choose option [PDF] academia.edu.
  44. ↑ Yang A, et al. (January 2021). "Effects of Dietary Cottonseed Oil and Cottonseed Meal Supplementation on Liver Lipid Content, Fatty Acid Profile and Hepatic Function in Laying Hens". Animals. 11 (1): 78. doi: 10.3390/ani11010078 . PMC   7824706 . PMID   33406775.
  45. ↑ "Oil, corn". FoodData Central. USDA. December 2019.
  46. ↑ Masoodi L, et al. (September 2022). "An Overview on Traditional vs. Green Technology of Extraction Methods for Producing High Quality Walnut Oil". Agronomy. 12 (10): 2258. doi: 10.3390/agronomy12102258 .
  47. ↑ "Oil, walnut". FoodData Central. USDA. April 2019. Retrieved 31 July 2024.
  48. ↑ "Oil, soybean". FoodData Central. USDA. December 2019.
  49. ↑ Dunford, Nurhan (August 2021). "Sesame Seed Oil Properties". OSU Extension. Retrieved 1 August 2024.
  50. ↑ Oboulbiga EB, et al. (June 2023). "Physicochemical, potential nutritional, antioxidant and health properties of sesame seed oil: a review". Front. Nutr. 10. Table 2. doi: 10.3389/fnut.2023.1127926 . PMC   10292629 . PMID   37377483.
  51. ↑ Nawirska-Olszańska A, Kita A, Biesiada A, Sokół-Łętowska A, Kucharska AZ (2013). "Characteristics of antioxidant activity and composition of pumpkin seed oils in 12 cultivars". Food Chemistry. 139 (1–4): 155–161. doi:10.1016/j.foodchem.2013.02.009. PMID   23561092.
  52. ↑ Wu, Hao; Shi, John; Xue, Sophia; Kakuda, Yukio; Wang, Dongfeng; Jiang, Yueming; Ye, Xingqian; Li, Yanjun; Subramanian, Jayasankar (2011). "Essential oil extracted from peach (Prunus persica) kernel and its physicochemical and antioxidant properties". LWT - Food Science and Technology. 44 (10): 2032–2039. doi:10.1016/j.lwt.2011.05.012.
  53. ↑ "Oil, canola". FoodData Central. USDA. December 2019.
  54. ↑ "Oil, sunflower". FoodData Central. USDA. April 2021.
  55. ↑ Nutter MK, Lockhart EE, Harris RS (1943). "The chemical composition of depot fats in chickens and turkeys". Journal of the American Oil Chemists' Society. 20 (11): 231–234. doi:10.1007/BF02630880. S2CID   84893770.
  56. ↑ "Oil, peanut". FoodData Central. USDA. April 2021.
  57. ↑ "Oil, flaxseed, cold pressed". FoodData Central. USDA. April 2019.
  58. ↑ "Oil, olive, extra virgin". FoodData Central. USDA. December 2019.
  59. ↑ "Earth News: Ancient 'smell of death' revealed". BBC. 9 September 2009.
  60. ↑ Li, Jun; Guasch-Ferré, Marta; Li, Yanping; Hu, Frank B. (2020). "Dietary intake and biomarkers of linoleic acid and mortality: systematic review and meta-analysis of prospective cohort studies". The American Journal of Clinical Nutrition. 112 (1): 150–167. doi:10.1093/ajcn/nqz349. PMC   7326588 . PMID   32020162.
  61. ↑ 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.
  62. ↑ 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.
  63. ↑ "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.
  64. ↑ 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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