List of unsaturated fatty acids

Last updated

ω−nCommon NameLipid NumbersΔnStructural FormulaTrans or CisNaturally Occurring in
ω−3 α-Linolenic acid C18:3Δ9,12,15CH3CH2CH=CHCH2CH=CHCH2CH=CH(CH2)7COOHcisflaxseeds, chia seeds, walnuts [1]
ω−3 Stearidonic acid C18:4Δ6,9,12,15CH3CH2CH=CHCH2CH=CHCH2CH=CHCH2CH=CH(

CH2)4COOH

cisseed oils of hemp, blackcurrant, corn gromwell [ citation needed ]
ω−3 Eicosapentaenoic acid C20:5Δ5,8,11,14,17CH3CH2CH=CHCH2CH=CHCH2CH=CHCH2CH=CHCH2

CH=CH(CH2)3COOH

ciscod liver, herring, mackerel, salmon, menhaden and sardine [ citation needed ]
ω−3 Cervonic acid C22:6Δ4,7,10,13,16,19CH3CH2CH=CHCH2CH=CHCH2CH=CHCH2CH=CHCH2

CH=CHCH2CH=CH(CH2)2COOH

cismaternal milk, fish oil [2]
ω−6 Linoleic acid C18:2Δ9,12CH3(CH2)4CH=CHCH2CH=CH(CH2)7COOHcispeanut oil, [3] chicken fat, [4] olive oil [5] [6]
ω−6 Linolelaidic acid C18:2CH3(CH2)4CH=CHCH2CH=CH(CH2)7COOHtranspartially hydrogenated vegetable oils
ω−6 γ-Linolenic acid C18:3Δ6,9,12CH3(CH2)4CH=CHCH2CH=CHCH2CH=CH(CH2)4COOHcisborage oil, black currant oil, evening primrose oil [7] and safflower oil [8]
ω−6 Dihomo-γ-linolenic acid C20:3Δ8,11,14CH3(CH2)4CH=CHCH2CH=CHCH2CH=CH(CH2)6COOHcisonly in trace amounts in animal products [9] [10]
ω−6 Arachidonic acid C20:4Δ5,8,11,14CH3(CH2)4CH=CHCH2CH=CHCH2CH=CHCH2

CH=CH(CH2)3COOH

cis
ω−6 Docosatetraenoic acid C22:4Δ7,10,13,16CH3(CH2)4CH=CHCH2CH=CHCH2CH=CHCH2

CH=CH(CH2)5COOH

cis
ω−7 Palmitoleic acid C16:1Δ9CH3(CH2)5CH=CH(CH2)7COOHcismacadamia nuts [11]
ω−7 Vaccenic acid C18:1Δ11CH3(CH2)5CH=CH(CH2)9COOHtrans dairy products such as milk, butter, and yogurt [12]
ω−7 Paullinic acid C20:1Δ13CH3(CH2)5CH=CH(CH2)11COOHcis guarana [13]
ω−9 Oleic acid C18:1Δ9CH3(CH2)7CH=CH(CH2)7COOHcis olive oil, pecan oil, [14] canola oil [15]
ω−9 Elaidic acid C18:1Δ9CH3(CH2)7CH=CH(CH2)7COOHtrans hydrogenated vegetable oil [16]
ω−9 Gondoic acid C20:1Δ11CH3(CH2)7CH=CH(CH2)9COOHcis jojoba oil [17] (edible but non-caloric and non-digestible)
ω−9 Erucic acid C22:1Δ13CH3(CH2)7CH=CH(CH2)11COOHciswallflower seed, mustard oil
ω−9 Nervonic acid C24:1Δ15CH3(CH2)7CH=CH(CH2)13COOHcis King salmon, flaxseed, sockeye salmon, sesame seed, macadamia nuts [18]
ω−9 Mead acid C20:3Δ5,8,11CH3(CH2)7CH=CHCH2CH=CHCH2CH=CH(CH2)3COOHcis cartilage

Fatty acid molecular species

Mono-unsaturated fatty acid

The following fatty acids have one unsaturated bond.

Contents

Crotonic acid

Crotonic acid has 4 carbons, is included in croton oil, and is a trans-2-mono-unsaturated fatty acid. C3H5 CO2H, IUPAC organization name (E)-but-2-enoic acid, trans-but-2-enoic acid, numerical representation 4:1, n-1, molecular weight 86.09, melting point 72–74 °C, boiling point 180–181 °C, specific gravity 1.027. CAS registry number 107-93-7.

Crotonic acid1.svg

Myristoleic

Myristoleic acid has 14 carbons, is found in whale blubber, and is a cis-9-monounsaturated fatty acid. C13H25CO2H, IUPAC organization name (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.

Myristoleic acid.svg

Palmitoleic acid

Palmitoleic acid has 16 carbons, is found in cod liver oil, sardine oil, and herring oil, and is a cis-9-monounsaturated fatty acid. C15H29CO2H, IUPAC organization name (Z)-hexadec-9-enoic acid, n-7, numerical representation of 16:1, molecular weight 254.41, melting point 5 °C, specific gravity 0.894. CAS Registry Number 373-49-9.

Palmitoleic acid1.svg

Sapienic acid

Sapienic acid has 16 carbons, is found in the skin, and is a cis-6-mono-unsaturated fatty acid. C15H29CO2H, IUPAC organization name (Z)-6-Hexadecenoic acid, n-10, numerical expression 16:1, molecular weight 254.41. CAS Registry Number 17004-51-2.

Oleic acid

Oleic acid has 18 carbons, is found in most animal fats and olive oil, and is a cis-9-monounsaturated fatty acid. C17H33CO2H, IUPAC organization name (Z)-octadec-9-enoic acid, numerical representation 18:1 (9), n-9, molecular weight 282.46, melting point 13.4 °C, specific gravity 0.891. CAS Registry Number 112-80-1.

Oleic acid.svg

Elaidic acid

Elaidic acid has 18 carbons and is a trans-9-mono-unsaturated fatty acid. It is also a trans isomer of oleic acid. C17H33CO2H, IUPAC organization name (E)-octadec-9-enoic acid, numerical representation 18:1 (9), n-9, molecular weight 282.46, melting point 43–45 °C. CAS Registry Number 112-79-8.

Elaidic acid.svg

Vaccenic acid

Vaccenic acid has 18 carbons, is found in beef tallow, mutton, and butter, and is a trans-11-mono-unsaturated fatty acid. C17H33CO2H, IUPAC organization name (E)-octadec-11-enoic acid, numerical representation 18:1 (11) n-7, molecular weight 282.46. CAS Registry Number 506-17-2.

Vaccenic Acid.svg

Gadoleic acid

Gadoleic acid has 20 carbons, is found in cod liver oil and other marine animal oils, and is a cis-9-mono-unsaturated fatty acid. C19H37CO2H, IUPAC organization name (Z)-icos-9-enoic acid, numerical representation 20:1 (9), n-11, molecular weight 310.51. CAS Registry Number 29204-02-2.

Gadoleic acid.svg

Eicosenoic acid

Eicosenoic acid has 20 carbons, is found in a wide variety of plant oils, and is a cis-11-mono-unsaturated fatty acid. C19H37CO2H, IUPAC organization name (Z)-icos-11-enoic acid, numerical representation 20:1 (11), n-9, molecular weight 310.51. CAS Registry Number 5561-99-9.

Eicosenoic acid.svg

Erucic acid

Erucic acid has 22 carbons, is found in rapeseed oil and mustard oil, and is a cis-13-monounsaturated is a fatty acid. C21H41CO2H, IUPAC organization name (Z)-docos-13-enoic acid, numerical representation 22:1, n-9, molecular weight 338.57, melting point 33–35 °C. CAS Registry Number 112-86-7.

Erucic acid.svg

Nervonic acid

Nervonic acid has 24 carbons, is found in brain glycolipids (Nervon) and sphingomyelin, and is a cis-15-mono-unsaturated fatty acid. C23H45CO2H, IUPAC organization name (Z)-tetracos-15-enoic acid, numerical representation 24:1, n-9, molecular weight 366.62, melting point 42–43 °C. CAS Registry Number 506-37-6.

Nervonic acid.svg

Di-unsaturated fatty acid

The following fatty acids have two unsaturated bonds.

Linoleic acid

Linoleic acid has 18 carbons, is contained in many vegetable oils, particularly semi-drying oils, and is a cis-9-cis-12-di-unsaturated fatty acid. C17H31CO2H, IUPAC organization name (9Z, 12Z)-octadeca-9,12-dienoic acid, numerical representation 18:2 (9,12), n-6, molecular weight 280.45, melting point −5 °C, specific gravity 0.902. CAS Registry Number 60-33-3. There are isomers of linoleic acid with double bonds separated by one single bond. They are named conjugated linoleic acids.

Linoleic acid.svg

Eicosadienoic acid

Eicosadienoic acid (eicosadienoic's) has 20 carbons and is a cis-11-cis-14-di-unsaturated fatty acid. C19H35CO2H, IUPAC organization name (11Z, 14Z)-icosa-11,14-dienoic acid, numerical representation 20:2 (11,14), n-6, molecular weight 308.50.

Eicosadienoic acid.svg

Docosadienoic acid

Docosadienoic acid (docosadienoic's) has 22 carbons and is a cis-13-cis-16-di-unsaturated fatty acid. C21H39CO2H, IUPAC organization name (13Z, 16Z)-docosa-13,16-dienoic acid, numerical representation 22:2 (13,16), n-6, molecular weight 336.55. CAS Registry Number 7370-49-2.

Docosadienoic acid.svg

Tri-unsaturated fatty acids

The following fatty acids have three unsaturated bonds.

Linolenic acid

α-Linolenic acid (alpha-linolenic's) has 18 carbons, is found in linseed oil and drying oil, and is a 9,12,15-tri-unsaturated fatty acid. C17H29CO2H, IUPAC organization name (9Z, 12Z, 15Z)-octadeca-9,12,15-trienoic acid, numerical representation 18:3 (9,12,15), n-3, molecular weight 278.43, melting point −11 °C, specific gravity 0.914. CAS Registry Number 463-40-1.

Alpha-linolenic acid.svg

γ-Linolenic acid (gamma-linolenic's) has 18 carbons, is the structural isomer of α-linolenic acid. IUPAC organization name (6Z, 9Z, 12Z)-octadeca-6,9,12-trienoic acid, numerical representation 18:3 (6,9,12), n-6. CAS Registry Number 506-26-3.

Gamma-linolenic acid.svg

Pinolenic acid

Pinolenic acid (pinolenic's) has 18 carbons, is found in pine nuts, and is a 5,9,12-triunsaturated fatty acid. C17H29CO2H, IUPAC organization name (5Z, 9Z, 12Z)-octadeca-5,9,12-trienoic acid, numerical representation 18:3 (5,9,12), n-6, molecular weight 278.43. CAS Registry Number 16833-54-8.

Pinolenic acid.svg

Eleostearic acid

α-Eleostearic acid (alpha-eleostearic's) has 18 carbons, is found in Kiri drying oil, and is a 9,11,13-triunsaturated fatty acid. C17H29CO2H, IUPAC organization name (9Z, 11E, 13E)-octadeca-9,11,13-trienoic acid, numerical representation 18:3 (9,11,13), n-5, molecular weight 278.43.

Alpha-eleostearic acid1.svg

β-Eleostearic acid (beta-eleostearic's, beta-eleostearic acid) is a geometric isomer of α-eleostearic acid. IUPAC organization name (9E, 11E, 13E)-octadeca-9,11,13-trienoic acid, numerical representation 18:3 (9,11,13), n-5.

Beta-eleostearic acid.svg
α- and β-Eleostearic acids are cis–trans isomers. Other cis–trans isomers of eleostearic acid are:

Catalpic acid (9E, 11E, 13Z)
Punicic acid (9Z, 11E, 13Z).

Mead acid

Mead acid (Mead's) has 20 carbons, is a 5,8,11-tri-unsaturated fatty acid. C19H33CO2H, IUPAC organization name (5Z, 8Z, 11Z)-icosa-5,8,11-trienoic acid, numerical representation 20:3 (5,8,11), n-9, molecular weight 306.48. CAS Registry Number 20590-32-3.

Mead acid1.svg

Dihomo-γ-linolenic acid

Dihomo-γ-linolenic acid (dihomo-gamma-linolenic's, dihomo-gamma-linolenic acid, DGLA) has 20 carbons, and is an 8,11,14-tri-unsaturated fatty acid. C19H33CO2H, IUPAC organization name (8Z, 11Z, 14Z)-icosa-8,11,14-trienoic acid, numerical representation 20:3 (8,11,14), n-6, molecular weight 306.48. CAS Registry Number 1783-84-2.

Dihomo-gamma-linolenic acid.svg

Eicosatrienoic acid

Eicosatrienoic acid (eicosatrienoic's, eicosatrienoic acid) has 20 carbons and is an 11,14,17- tri unsaturated fatty acid. C19H33CO2H, IUPAC organization name (11Z, 14Z, 17Z)-icosa-11,14,17-trienoic acid, numerical representation 20:3 (11,14,17), n-3, molecular weight 306.48.

Eicosatrienoic acid.svg

Tetra-unsaturated fatty acids

The following fatty acids have four unsaturated bonds.

Stearidonic acid

Stearidonic acid (stearidonic's) has 18 carbons, is found in sardine oil and herring oil, and is a 6,9,12,15-tetraunsaturated fatty acid. C17H27CO2H, IUPAC organization name (6Z, 9Z, 12Z, 15Z)-octadeca-6,9,12,15-tetraenoic acid, numerical representation 18:4 (6,9,12,15), n-3, molecular weight 276.41. CAS Registry Number 20290-75-9.

Stearidonic acid.svg

Arachidonic acid

Arachidonic acid (arachidonic's) has 20 carbons, is present in animal visceral fat (brain, liver, kidney, lung, spleen), and is a 5,8,11,14-tetra-unsaturated fatty acid. C19H31CO2H, IUPAC organization name (5Z, 8Z, 11Z, 14Z)-icosa-5,8,11,14-tetraenoic acid, numerical representation 20:4 (5,8,11,14), n-6, molecular weight 304.47, boiling point 169–171 °C. CAS Registry Number 506-32-1.

Arachidonic acid1.svg

In signal transduction, arachidonic acid is produced through decomposition of the phospholipid cell membrane. This gives rise to the arachidonic acid cascade, a metabolic pathway that yields lipid mediator compounds [19] such as prostaglandins, thromboxanes and leukotrienes. This pathway has attracted study for its key role in inflammatory diseases such as asthma. [20]

Eicosatetraenoic acid

Eicosatetraenoic acid (eicosatetraenoic's) has 20 carbons and is an 8,11,14,17-tetraunsaturated fatty acid. C19H31CO2H, IUPAC organization name (8Z, 11Z, 14Z, 17Z)-icosa-8,11,14,17-tetraenoic acid, numerical representation 20:4 (8,11,14,17), n-3, molecular weight 304.47.

Eicosatetraenoic acid.svg

Adrenic acid

Adrenic acid (adrenic'sd) has 22 carbons and is a 7,10,13,16-tetra-unsaturated fatty acid. C21H35CO2H, IUPAC organization name (7Z, 10Z, 13Z, 16Z)-docosa-7,10,13,16-tetraenoic acid, numerical representation 22:4 (7,10,13,16), n-6, molecular weight 332.52. CAS Registry Number 28874-58-0.

Adrenic acid.svg

Pentaunsaturated fatty acids

The following fatty acids have five unsaturated bonds.

Bosseopentaenoic acid

Bosseopentaenoic acid (Boseopentaen's), has 20 carbons and is a 5,8,10,12,14-pentaunsaturated fatty acid. C17H25CO2H, IUPAC organization name (5Z, 8Z, 10E, 12E, 14Z)-eicosa-5,8,10,12,14-pentaenoic acid, numerical representation 20:5 (5,8,10,12,14), n-6, molecular weight 302.46 g·mol−1. [21]

Eicosapentaenoic acid

Eicosapentaenoic acid (EPA) has 20 carbons, is found in fish oil, is a pentaunsaturated fatty acid. It is one of the essential fatty acids. The recommendation of ingesting fish oil supplements during pregnancy is said to help increase the cognitive ability at 6 months, but mercury concentration in fish products offsets the effect. In patients with hyperlipidemia and obstructive artery disease it can help lower triglycerides and also has an anti-platelet effect similar to other anti-platelet agents. It has also been shown to help in secondary prevention of ischemic heart disease as shown with the JELIS test.

C19H29CO2H, IUPAC organization name (5Z, 8Z, 11Z, 14Z, 17Z)-icosa-5,8,11,14,17-pentaenoic acid, numerical representation of 20:5 (5,8,11,14,17), n-3, molecular weight 302.45, melting point −54 – −53 °C, specific gravity 0.943. CAS Registry Number 10417-94-4.

Eicosapetaenoic acid.svg

Ozubondo acid

Ozubondo acid (Ozubondo's, Osbond acid), has 22 carbons, is a 4,7,10,13,16- pentaunsaturated fatty acid. C21H33CO2H, IUPAC organization name (4Z, 7Z, 10Z, 13Z, 16Z)-docosa-4,7,10,13,16-pentaenoic acid, numerical representation 22:5 (4,7,10,13,16), n-6, molecular weight 330.50. CAS Registry Number 25182-74-5

Osbond acid.svg

Sardine acid

Sardine acid (clupanodonic acid) has 22 carbons, is found in sardine oil and herring oil, is a 7,10,13,16,19- pentaunsaturated fatty acid. C21H33CO2H, IUPAC organization name (7Z, 10Z, 13Z, 16Z, 19Z)-docosa-7,10,13,16,19-pentaenoic acid, numerical representation 22:5 (7,10,13,16,19), n-3, molecular weight 330.50.

Clupanodonic acid.svg

Tetracosapentaenoic acid

Tetracosapentaenoic acid has 24 carbons, is a 9,12,15,18,21-penta unsaturated fatty acid. C23H37CO2H, IUPAC organization name (9Z, 12Z, 15Z, 18Z, 21Z)-tetracosa-9,12,15,18,21-pentaenoic acid, numerical representation 24:5 (9,12,15,18,21), n-3, molecular weight 358.56.

Tetracosapentaenoic acid.svg

Hexa-unsaturated fatty acids

The following fatty acids have six unsaturated bonds.

Cervonic acid

Cervonic acid (or docosahexaenoic acid) has 22 carbons, is found in fish oil, is a 4,7,10,13,16,19-hexa unsaturated fatty acid. In the human body its generation depends on consumption of omega 3 essential fatty acids (e.g., ALA or EPA), but the conversion process is inefficient. [22] C21H31CO2H, IUPAC organization name (4Z, 7Z, 10Z, 13Z, 16Z, 19Z)-docosa-4,7,10,13,16,19-hexaenoic acid, numerical representation 22:6 (4,7,10,13,16,19), n-3, molecular weight 328.49, melting point −44 °C, specific gravity 0.950. CAS Registry Number 6217-54-5.

Docosahexaenoic acid.svg

Herring acid

Herring acid (Herring's, Nisinic acid) is a 6,9,12,15,18,21-hexa unsaturated fatty acid with 24 carbon atoms. C23H35CO2H, IUPAC organization name (6Z, 9Z, 12Z, 15Z, 18Z, 21Z)-tetracosa-6,9,12,15,18,21-hexaenoic acid, numerical representation 24:6 (6,9,12,15,18,21), n-3, molecular weight 356.54.

Nisinic acid.svg

See also

Related Research Articles

<span class="mw-page-title-main">Fatty acid</span> Carboxylic acid

In chemistry, particularly in biochemistry, 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 chain of an even number of carbon atoms, from 4 to 28. Fatty acids are a major component of the lipids in some species such as microalgae but in some other organisms are not found in their standalone form, but instead exist as three main classes of esters: triglycerides, phospholipids, and cholesteryl esters. In any of these forms, fatty acids are both important dietary sources of fuel for animals and important structural components for cells.

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.

<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 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.

<span class="mw-page-title-main">Eicosanoid</span> Class of compounds

Eicosanoids are signaling molecules made by the enzymatic or non-enzymatic oxidation of arachidonic acid or other polyunsaturated fatty acids (PUFAs) that are, similar to arachidonic acid, around 20 carbon units in length. Eicosanoids are a sub-category of oxylipins, i.e. oxidized fatty acids of diverse carbon units in length, and are distinguished from other oxylipins by their overwhelming importance as cell signaling molecules. Eicosanoids function in diverse physiological systems and pathological processes such as: mounting or inhibiting inflammation, allergy, fever and other immune responses; regulating the abortion of pregnancy and normal childbirth; contributing to the perception of pain; regulating cell growth; controlling blood pressure; and modulating the regional flow of blood to tissues. In performing these roles, eicosanoids most often act as autocrine signaling agents to impact their cells of origin or as paracrine signaling agents to impact cells in the proximity of their cells of origin. Eicosanoids may also act as endocrine agents to control the function of distant cells.

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.

Eicosatetraenoic acid (ETA) designates any straight chain 20:4 fatty acid. Eicosatetraenoic acid belongs to the family of eicosanoids, molecules synthesized from oxidized polyunsaturated fatty acids (PUFAs) to mediate cell-cell communication. The eicosanoids, working in tandem, contribute to a lipid signaling complex widely responsible for inducing an inflammatory immune response. Common signs of inflammation are both internal and external, with effects like visible redness, pain in the surrounding area, swelling, and the sensation of heat—many of these an effect of varying eicosanoid species. These effects are associated with and have been observed in patients with cancers and various neurological/metabolic disorders.

Candlenut oil or kukui nut oil is extracted from the nut of Aleurites moluccanus, the candlenut or kuku'i.

Docosapentaenoic acid (DPA) designates any straight open chain polyunsaturated fatty acid (PUFA) which contains 22 carbons and 5 double bonds. DPA is primarily used to designate two isomers, all-cis-4,7,10,13,16-docosapentaenoic acid and all-cis-7,10,13,16,19-docosapentaenoic acid. They are also commonly termed n-6 DPA and n-3 DPA, respectively; these designations describe the position of the double bond being 6 or 3 carbons closest to the (omega) carbon at the methyl end of the molecule and is based on the biologically important difference that n-6 and n-3 PUFA are separate PUFA classes, i.e. the omega-6 fatty acids and omega-3 fatty acids, respectively. Mammals, including humans, can not interconvert these two classes and therefore must obtain dietary essential PUFA fatty acids from both classes in order to maintain normal health.

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

Hepoxilins (Hx) are a set of epoxyalcohol metabolites of polyunsaturated fatty acids (PUFA), i.e. they possess both an epoxide and an alcohol residue. HxA3, HxB3, and their non-enzymatically formed isomers are nonclassic eicosanoid derived from acid the (PUFA), arachidonic acid. A second group of less well studied hepoxilins, HxA4, HxB4, and their non-enzymatically formed isomers are nonclassical eicosanoids derived from the PUFA, eicosapentaenoic acid. Recently, 14,15-HxA3 and 14,15-HxB3 have been defined as arachidonic acid derivatives that are produced by a different metabolic pathway than HxA3, HxB3, HxA4, or HxB4 and differ from the aforementioned hepoxilins in the positions of their hydroxyl and epoxide residues. Finally, hepoxilin-like products of two other PUFAs, docosahexaenoic acid and linoleic acid, have been described. All of these epoxyalcohol metabolites are at least somewhat unstable and are readily enzymatically or non-enzymatically to their corresponding trihydroxy counterparts, the trioxilins (TrX). HxA3 and HxB3, in particular, are being rapidly metabolized to TrXA3, TrXB3, and TrXC3. Hepoxilins have various biological activities in animal models and/or cultured mammalian tissues and cells. The TrX metabolites of HxA3 and HxB3 have less or no activity in most of the systems studied but in some systems retain the activity of their precursor hepoxilins. Based on these studies, it has been proposed that the hepoxilins and trioxilins function in human physiology and pathology by, for example, promoting inflammation responses and dilating arteries to regulate regional blood flow and blood pressure.

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

Mead acid is an omega-9 fatty acid, first characterized by James F. Mead. As with some other omega-9 polyunsaturated fatty acids, animals can make Mead acid de novo. Its elevated presence in the blood is an indication of essential fatty acid deficiency. Mead acid is found in large quantities in cartilage.

<span class="mw-page-title-main">ALOX15</span> Lipoxygenase found in humans

ALOX15 is, like other lipoxygenases, a seminal enzyme in the metabolism of polyunsaturated fatty acids to a wide range of physiologically and pathologically important products. ▼ Gene Function

α-Parinaric acid Chemical compound

α-Parinaric acid is a conjugated polyunsaturated fatty acid. Discovered by Tsujimoto and Koyanagi in 1933, it contains 18 carbon atoms and 4 conjugated double bonds. The repeating single bond-double bond structure of α-parinaric acid distinguishes it structurally and chemically from the usual "methylene-interrupted" arrangement of polyunsaturated fatty acids that have double-bonds and single bonds separated by a methylene unit (−CH2−). Because of the fluorescent properties conferred by the alternating double bonds, α-parinaric acid is commonly used as a molecular probe in the study of biomembranes.

<span class="mw-page-title-main">Octadecatrienoic acid</span> Index of chemical compounds with the same name

An octadecatrienoic acid is a chemical compound with formula C
18H
30O
2, a polyunsaturated fatty acid whose molecule has an 18-carbon unbranched backbone with three double bonds.

<span class="mw-page-title-main">Divinylether fatty acids</span>

Divinylether fatty acids contain a fatty acid chemically combined with a doubly unsaturated carbon chain linked by an oxygen atom (ether). Fatty acid hydroperoxides generated by plant lipoxygenases from linoleic and linolenic acids are known to serve as substrates for a divinyl ether synthase which produces divinyl ether fatty acids. Up to date divinyl ethers were detected only within the plant kingdom.

<span class="mw-page-title-main">Epoxydocosapentaenoic acid</span> Group of chemical compounds

Epoxide docosapentaenoic acids are metabolites of the 22-carbon straight-chain omega-3 fatty acid, docosahexaenoic acid (DHA). Cell types that express certain cytochrome P450 (CYP) epoxygenases metabolize polyunsaturated fatty acids (PUFAs) by converting one of their double bonds to an epoxide. In the best known of these metabolic pathways, cellular CYP epoxygenases metabolize the 20-carbon straight-chain omega-6 fatty acid, arachidonic acid, to epoxyeicosatrienoic acids (EETs); another CYP epoxygenase pathway metabolizes the 20-carbon omega-3 fatty acid, eicosapentaenoic acid (EPA), to epoxyeicosatetraenoic acids (EEQs). CYP epoxygenases similarly convert various other PUFAs to epoxides. These epoxide metabolites have a variety of activities. However, essentially all of them are rapidly converted to their corresponding, but in general far less active, vicinal dihydroxy fatty acids by ubiquitous cellular soluble epoxide hydrolase. Consequently, these epoxides, including EDPs, operate as short-lived signaling agents that regulate the function of their parent or nearby cells. The particular feature of EDPs distinguishing them from EETs is that they derive from omega-3 fatty acids and are suggested to be responsible for some of the beneficial effects attributed to omega-3 fatty acids and omega-3-rich foods such as fish oil.

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

Epoxyeicosatetraenoic acids are a set of biologically active epoxides that various cell types make by metabolizing the omega 3 fatty acid, eicosapentaenoic acid (EPA), with certain cytochrome P450 epoxygenases. These epoxygenases can metabolize EPA to as many as 10 epoxides that differ in the site and/or stereoisomer of the epoxide formed; however, the formed EEQs, while differing in potency, often have similar bioactivities and are commonly considered together.

Pentenoic acid is any of five mono-carboxylic acids whose molecule has an unbranched chain of five carbons connected by three single bonds and one double bond. That is, any compound with one of the formulas HO(O=)C−CH=CH−CH2−CH3 (2-pentenoic), HO(O=)C−CH2−CH=CH−CH3 (3-pentenoic), or HO(O=)C−CH2−CH2−CH=CH2 (4-pentenoic). In the IUPAC-recommended nomenclature, these acids are called pent-2-enoic, pent-3-enoic, and pent-4-enoic, respectively. All these compounds have the empirical formula C
5H
8O
2.

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

Sciadonic acid, also known as eicosatrienoic acid, is a polyunsaturated fatty acid. In regard to its structure, 5Z,11Z,14Z-eicosa-5,11,14-trienoic acid has 3 double bonds in the 5, 11, and 14 positions all of which are in the cis configuration. It is further classified as Δ5-fatty, and an omega-6 acid due to the methylene interrupted double bond at carbon-5 and a final double bond 6 carbons away from the methylene tail of the hydrocarbon. Sciadonic acid is a naturally occurring compound and has been found to play a role as a plant metabolite, commonly found in pine nut oil. Furthermore, there have been propositions of several health applications for sciadonic acid as an anti-inflammatory agent. Sharing close structural similarity to arachidonic acid, sciadonic acid acts as a replacement phospholipid in the corresponding biochemical pathways.

References

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  2. ↑ Guesnet P, Alessandri JM (2011). "Docosahexaenoic acid (DHA) and the developing central nervous system (CNS) - Implications for dietary recommendations". Biochimie. 93 (1): 7–12. doi:10.1016/j.biochi.2010.05.005. PMID   20478353.
  3. ↑ Oil, peanut, salad or cooking: search for peanut oil on "USDA Food Composition Databases". Archived from the original on 2015-03-03. Retrieved 2011-11-14.
  4. ↑ M. K. Nutter, E. E. Lockhart and R. S. Harris (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.
  5. ↑ "Olive Oil : Chemical Characteristics".
  6. ↑ Beltran; Del Rio, C; Sánchez, S; Martínez, L; et al. (2004). "Influence of Harvest Date and Crop Yield on the Fatty Acid Composition of Virgin Olive Oils from Cv. Picual" (PDF). J. Agric. Food Chem. 52 (11): 3434–3440. doi:10.1021/jf049894n. PMID   15161211.
  7. ↑ "Conditions We Treat".
  8. ↑ Flider, Frank J. (2013). "Development and commercialization of GLA safflower oil". Lipid Technology. 25 (10): 227–229. doi:10.1002/lite.201300302.
  9. ↑ Horrobin, D. F., 1990a. Gamma linolenic acid. Rev. Contemp. Pharmacother. 1, 1-45
  10. ↑ Huang, Y.-S. and Mills, D. E. (Eds.), 1996. Gamma-linolenic acid metabolism and its roles in nutrition and medicine. AOCS Press, Champaign, Illinois, 319 pp.
  11. ↑ "Nuts, macadamia nuts, raw". NutritionData.com.
  12. ↑ Natural trans fats may be good for you. May 19, 2008
  13. ↑ Avato, P; Pesante, MA; Fanizzi, FP; Santos, CA (2003). "Seed oil composition of Paullinia cupana var. Sorbilis (Mart.) Ducke". Lipids. 38 (7): 773–80. doi:10.1007/s11745-003-1126-5. PMID   14506841. S2CID   4026737.
  14. ↑ Villarreal-Lozoya, Jose E.; Lombardini, Leonardo; Cisneros-Zevallos, Luis (2007). "Phytochemical constituents and antioxidant capacity of different pecan Carya illinoinensis (Wangenh.) K. Koch] cultivars". Food Chemistry. 102 (4): 1241. doi:10.1016/j.foodchem.2006.07.024.
  15. ↑ "Comparison of Dietary Fats Chart". Canola Council of Canada. Archived from the original on 2008-06-06. Retrieved 2008-09-03.
  16. ↑ Abbey M, Nestel PJ (1994). "Plasma cholesteryl ester transfer protein activity is increased when trans-elaidic acid is substituted for cis-oleic acid in the diet". Atherosclerosis. 106 (1): 99–107. doi:10.1016/0021-9150(94)90086-8. PMID   8018112.
  17. ↑ Miwa, Thomas (1971). "Jojoba Oil Wax Esters and Derived Fatty Acids and Alcohols: Gas Chromatographic Analyses". Journal of the American Oil Chemists' Society. 48 (6): 259–264. doi:10.1007/bf02638458. S2CID   1466516 . Retrieved May 6, 2013.
  18. ↑ "Foods highest in 24:1 C".
  19. ↑ Edwards; McCarthy; Wenceslau (2020). "ch. 3.1: Arachidonic Acid-Derived Bioactive Lipids". Current Pharmaceutical Design. 26 (30): 3723–3732. doi:10.2174/1381612826666200417150121. PMC   7542659 .
  20. ↑ Wang, B.; Wu, L.; Chen, J; et al. (2021). "Metabolism pathways of arachidonic acids". Signal Transduction and Targeted Therapy. 6 (64). doi: 10.1038/s41392-020-00443-w . PMC   7910446 .
  21. ↑ Burgess, J.R.; De la Rosa, R.I.; Jacobs, R.S.; Butler, A (1991). "A new eicosapentaenoic acid formed from arachidonic acid in the coralline red algae Bossiella orbigniana". Lipids. 26 (2): 1057–1059. doi:10.1007/BF02544012
  22. ↑ Gropper, Sareen Annora Stepnick; Smith, Jack L.; Carr, Timothy P. Advanced nutrition and human metabolism (7 ed.). Australia. ISBN   9781305627857. OCLC   988914315.
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