List of unsaturated fatty acids on:
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γ-linolenic acid (gamma-linolenic's) has 18 carbons, the structural isomers of α- linolenic acid. IUPAC organization name (6''Z '', 9''Z '', 12''Z'')-octadeca-6,9,12-trienoic acid, numerical representation 18: 3 (6, 9, 12), n-6. CAS Registry Number 506-26-3.
β-eleostearic acid (beta-eleostearic's, beta-eleostearic acid) is a geometric isomer of α- eleostearic acid. IUPAC organization name (9''E '', 11''E '', 13''E'')-octadeca-9,11,13-trienoic acid, numerical representation 18: 3 (9, 11, 13), n-5.
In
Fatty acid molecular species
Mono-unsaturated fatty acid
The following fatty acids have one unsaturated bond.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
A CAS Registry Number (also referred to as CAS RN or informally CAS Number) is a unique identification number assigned by the Chemical Abstracts Service (CAS), US to every chemical substance described in the open scientific literature. It inclu ...
107-93-7.
Myristoleic
Myristoleic acid has 14 carbons, is found inwhale
Whales are a widely distributed and diverse group of fully aquatic placental marine mammals. As an informal and colloquial grouping, they correspond to large members of the infraorder Cetacea, i.e. all cetaceans apart from dolphins and ...
blubber
Blubber is a thick layer of vascularized adipose tissue under the skin of all cetaceans, pinnipeds, penguins, and sirenians.
Description
Lipid-rich, collagen fiber-laced blubber comprises the hypodermis and covers the whole body, except ...
, 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.
Palmitoleic acid
Palmitoleic acid has 16 carbons, is found in cod liver oil,sardine oil
"Sardine" and "pilchard" are common names for various species of small, oily forage fish in the herring family Clupeidae. The term "sardine" was first used in English during the early 15th century, a folk etymology says it comes from the Ita ...
, and herring oil
Herring are forage fish, mostly belonging to the family of Clupeidae.
Herring often move in large schools around fishing banks and near the coast, found particularly in shallow, temperate waters of the North Pacific and North Atlantic Ocea ...
, 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.
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
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. In chemical terms, oleic acid is classified as a monounsaturated om ...
has 18 carbons, is found in most animal fats and olive oil
Olive oil is a liquid fat obtained from olives (the fruit of ''Olea europaea''; family Oleaceae), a traditional tree crop of the Mediterranean Basin, produced by pressing whole olives and extracting the oil. It is commonly used in cooking: ...
, 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.
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.
Vaccenic acid
Vaccenic acid has 18 carbons, is found in beef tallow,mutton
Lamb, hogget, and mutton, generically sheep meat, are the meat of domestic sheep, ''Ovis aries''. A sheep in its first year is a lamb and its meat is also lamb. The meat from sheep in their second year is hogget. Older sheep meat is mutton. Ge ...
, and butter
Butter is a dairy product made from the fat and protein components of churned cream. It is a semi-solid emulsion at room temperature, consisting of approximately 80% butterfat. It is used at room temperature as a spread (food), spread, melted a ...
, 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.
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.
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.
Erucic acid
Erucic acid has 22 carbons, is found inrapeseed oil
Close-up of canola blooms
Canola flower
Rapeseed oil is one of the oldest known vegetable oils. There are both edible and industrial forms produced from rapeseed, the seed of several cultivars of the plant family Brassicaceae. Historically, ...
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.
Nervonic acid
Nervonic acid
Nervonic acid (24:1, n−9) is a fatty acid. It is a monounsaturated analog of lignoceric acid (24:0). It is also known as selacholeic acid and ''cis''-15-tetracosenoic acid. Its name derives from the Latin word '' nervus'', meaning nerve or si ...
has 24 carbons, is found in brain
The brain is an organ that serves as the center of the nervous system in all vertebrate and most invertebrate animals. It consists of nervous tissue and is typically located in the head ( cephalization), usually near organs for special ...
glycolipids (Nervon) and sphingomyelin
Sphingomyelin (SPH, ˌsfɪŋɡoˈmaɪəlɪn) is a type of sphingolipid found in animal cell membranes, especially in the membranous myelin sheath that surrounds some nerve cell axons. It usually consists of phosphocholine and ceramide, or a ethano ...
, 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.
Di-unsaturated fatty acid
The following fatty acids have two unsaturated bonds.Linoleic acid
Linoleate 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 (9''Z '', 12''Z'')-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 is a double bond is conjugated as an isomer conjugated linoleic acid.
Eicosadienoic acid
Eicosadienoic acid (eicosadienoic's) has 20 carbons and is a ''cis''-11-''cis''14-di-unsaturated fatty acid. C19H35CO2H, IUPAC organization name (11''Z '', 14''Z'')-icosa- 11,14-dienoic acid, numerical representation 20: 2 (11,14), n-6, molecular weight 308.50.
Docosadienoic acid
Docosadienoic acid (docosadienoic's) has 22 carbons and is a ''cis''-13-''cis''16-di-unsaturated fatty acid. C21H39CO2H, IUPAC organization name (13''Z '', 16''Z'')-docosa- 13,16-dienoic acid, numerical representation 22: 2 (13,16), n-6, molecular weight 336.55. CAS Registry Number 7370-49-2.
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 inlinseed oil
Linseed oil, also known as flaxseed oil or flax oil (in its edible form), is a colourless to yellowish oil obtained from the dried, ripened seeds of the flax plant (''Linum usitatissimum''). The oil is obtained by Expeller pressing, pressing, some ...
and drying oil
A drying oil is an oil that hardens to a tough, solid film after a period of exposure to air, at room temperature. The oil hardens through a chemical reaction in which the components crosslink (and hence, polymerize) by the action of oxygen ( ...
, and is a 9,12,15-tri-unsaturated fatty acid. C17H29CO2H, IUPAC organization name (9''Z '', 12''Z '', 15 '' Z'')-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.
γ-linolenic acid (gamma-linolenic's) has 18 carbons, the structural isomers of α- linolenic acid. IUPAC organization name (6''Z '', 9''Z '', 12''Z'')-octadeca-6,9,12-trienoic acid, numerical representation 18: 3 (6, 9, 12), n-6. CAS Registry Number 506-26-3.
Pinolenic acid
Pinolenic acid (pinolenic's) has 18 carbons, is found inpine
A pine is any conifer tree or shrub in the genus ''Pinus'' () of the family (biology), family Pinaceae. ''Pinus'' is the sole genus in the subfamily Pinoideae. The World Flora Online created by the Royal Botanic Gardens, Kew and Missouri Botanic ...
nuts, and is a 5,9,12-triunsaturated fatty acid. C17H29CO2H, IUPAC organization name (5''Z '', 9''Z '', 12 '' Z'')-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.
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 (9''E '', 11''E '', 13 '' Z'')-octadeca-9,11,13-trienoic acid, numerical representation 18: 3 (9,11,13), n-5, molecular weight 278.43.
β-eleostearic acid (beta-eleostearic's, beta-eleostearic acid) is a geometric isomer of α- eleostearic acid. IUPAC organization name (9''E '', 11''E '', 13''E'')-octadeca-9,11,13-trienoic acid, numerical representation 18: 3 (9, 11, 13), n-5.
Mead acid
Mead acid (Mead's) has 20 carbons, is a 5,8,11-tri-unsaturated fatty acid. C19H33CO2H, IUPAC organization name (5''Z '', 8''Z '', 11 '' Z'')-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.
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 (8''Z '', 11''Z '', 14 '' Z'')-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.
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 (11''Z '', 14''Z '', 17 '' Z'')-icosa-11,14,17-trienoic acid, numerical representation 20: 3 (11,14,17), n-3, molecular weight 306.48.
Tetra-unsaturated fatty acids
The following fatty acids have four unsaturated bonds.Stearidonic acid
Stearidonic acid
Stearidonic acid (SDA: C18 H28 O2; 18: 4, n-3) is an ω-3 fatty acid, sometimes called moroctic acid. It is biosynthesized from alpha-linolenic acid (ALA: C18H30O2; 18:3, n-3) by the enzyme delta-6-desaturase, that removes two hydrogen (H) ato ...
(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 (6''Z '', 9''Z '', 12 '' Z '', 15''Z'')-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.
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 (5''Z '', 8''Z '', 11 '' Z '', 14''Z'')-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.
In signal transduction
Signal transduction is the process by which a chemical or physical signal is transmitted through a cell as a series of molecular events, most commonly protein phosphorylation catalyzed by protein kinases, which ultimately results in a cellular ...
, arachidonic acid is produced through decomposition of the phospholipid
Phospholipids, are a class of lipids whose molecule has a hydrophilic "head" containing a phosphate group and two hydrophobic "tails" derived from fatty acids, joined by an alcohol residue (usually a glycerol molecule). Marine phospholipids ty ...
cell membrane
The cell membrane (also known as the plasma membrane (PM) or cytoplasmic membrane, and historically referred to as the plasmalemma) is a biological membrane that separates and protects the interior of all cells from the outside environment (the ...
. This gives rise to the arachidonic acid cascade
The two essential fatty acids are omega 3 and omega 6, which are required for a good human health. However, the effects of the ω-3 (omega-3) and ω-6 (omega-6) essential fatty acids (EFAs) are characterized by their interactions. The interac ...
, a metabolic pathway
In biochemistry, a metabolic pathway is a linked series of chemical reactions occurring within a cell. The reactants, products, and intermediates of an enzymatic reaction are known as metabolites, which are modified by a sequence of chemical ...
that yields lipid mediator compounds such as prostaglandin
The prostaglandins (PG) are a group of physiologically active lipid compounds called eicosanoids having diverse hormone-like effects in animals. Prostaglandins have been found in almost every tissue in humans and other animals. They are der ...
s, thromboxane
Thromboxane is a member of the family of lipids known as eicosanoids. The two major thromboxanes are thromboxane A2 and thromboxane B2. The distinguishing feature of thromboxanes is a 6-membered ether-containing ring.
Thromboxane is named for ...
s and leukotriene
Leukotrienes are a family of eicosanoid inflammatory mediators produced in leukocytes by the oxidation of arachidonic acid (AA) and the essential fatty acid eicosapentaenoic acid (EPA) by the enzyme arachidonate 5-lipoxygenase.
Leukotrie ...
s. This pathway has attracted study for its key role in inflammatory diseases such as asthma
Asthma is a long-term inflammatory disease of the airways of the lungs. It is characterized by variable and recurring symptoms, reversible airflow obstruction, and easily triggered bronchospasms. Symptoms include episodes of wheezing, c ...
.
Eicosatetraenoic acid
Eicosatetraenoic acid (eicosatetraenoic's) has 20 carbons and is an 8,11,14,17-tetraunsaturated fatty acid. C19H31CO2H, IUPAC organization name (8''Z '', 11''Z '', 14 '' Z '', 17''Z'')-icosa-8,11,14,17-tetraenoic acid, numerical representation 20: 4 (8,11,14,17), n-3, molecular weight 304.47.
Adrenic acid
Adrenic acid
Docosatetraenoic acid designates any straight chain 22:4 fatty acid. (''See'' essential fatty acid for nomenclature.)
One isomer is of particular interest:
* all-''cis''-7,10,13,16-docosatetraenoic acid is an ω-6 fatty acid with the common nam ...
(adrenic'sd) has 22 carbons and is a 7,10,13,16-tetra-unsaturated fatty acid. C21H35CO2H, IUPAC organization name (7''Z '', 10''Z '', 13 '' Z '', 16''Z'')-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.
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 (5''Z '', 8''Z '', 10 '' E '', 12''E '', 14''Z'')-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.Eicosapentaenoic acid
Eicosapentaenoic acid
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- ...
(EPA) has 20 carbons, is found in fish oil, is a pentaunsaturated fatty acid. It is one of the essential fatty acids
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.
Only two fatty acids are known to be essential for humans: alpha-linolenic a ...
. The recommendation of ingesting fish oil supplement
Supplement or Supplemental may refer to:
Health and medicine
* Bodybuilding supplement
* Dietary supplement
* Herbal supplement
Media
* Supplement (publishing), a publication that has a role secondary to that of another preceding or concurre ...
s 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
Hyperlipidemia is abnormally elevated levels of any or all lipids (fats, cholesterol, or triglycerides) or lipoproteins in the blood. citing: and The term ''hyperlipidemia'' refers to the laboratory finding itself and is also used as an umbr ...
and obstructive artery disease it can help lower triglycerides
A triglyceride (TG, triacylglycerol, TAG, or triacylglyceride) is an ester derived from glycerol and three fatty acids (from ''tri-'' and '' glyceride'').
Triglycerides are the main constituents of body fat in humans and other vertebrates, as ...
and also has an anti-platelet
Platelets, also called thrombocytes (from Greek θρόμβος, "clot" and κύτος, "cell"), are a component of blood whose function (along with the coagulation factors) is to react to bleeding from blood vessel injury by clumping, thereby i ...
effect similar to other anti-platelet agent
An antiplatelet drug (antiaggregant), also known as a platelet agglutination inhibitor or platelet aggregation inhibitor, is a member of a class of pharmaceuticals that decrease platelet aggregation and inhibit thrombus formation. They are effecti ...
s. It has also been shown to help in secondary prevention of ischemic heart disease as shown with the JELIS test.
C19H29CO2H, IUPAC organization name (5''Z '', 8''Z '', 11 '' Z '', 14''Z '', 17''Z'')-icosa-5,8,11,14,17-pentaenoic acid, numerical representation of 20: 5 (5,8,11,14,17), n-3, molecular weight 302.45, from melting point -54 -53 °C, specific gravity 0.943. CAS Registry Number 10417-94-4.
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 (4''Z '', 7''Z '', 10''Z '', 13''Z '', 16''Z'')-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
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 (7''Z '', 10''Z '', 13 '' Z '', 16''Z '', 19''Z'')-docosa-7,10,13,16,19-pentaenoic acid, numerical representation 22: 5 (7,10,13,16,19), n-3, molecular weight 330.50.
Tetracosanolpentaenoic acid
Tetracosanolpentaenoic acid has 24 carbons, is a 9,12,15,18,21-penta unsaturated fatty acid. C23H37CO2H, IUPAC organization name (9''Z '', 12''Z '', 15 '' Z '', 18''Z '', 21''Z'')-tetracosa-9,12,15,18,21-pentaenoic acid, numerical representation 24: 5 (9,12,15,18,21), n-3, molecular weight 358.56.
Hexa-unsaturated fatty acids
The following fatty acids have six unsaturated bonds.Cervonic acid
Cervonic acid (ordocosahexaenoic acid
Docosahexaenoic acid (DHA) is an omega-3 fatty acid that is a primary structural component of the human brain, cerebral cortex, skin, and retina. In physiological literature, it is given the name 22:6(n-3). It can be synthesized from alpha-li ...
) 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. C21H31CO2H, IUPAC organization name (4''Z'', 7''Z'', 10''Z'', 13''Z'', 16''Z'', 19''Z'')-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.
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 (6''Z '', 9''Z '', 12 '' Z '', 15''Z '', 18''Z '', 21''Z'')-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.
See also
* List of saturated fatty acids *Carboxylic acid
In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group () attached to an R-group. The general formula of a carboxylic acid is or , with R referring to the alkyl, alkenyl, aryl, or other group. Carboxyl ...
** List of carboxylic acids
* Dicarboxylic acid
References
{{Fatty acids Unsaturated Fatty Acids Alkenoic acids