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Polyunsaturated Fatty Acid
Polyunsaturated fatty acids (PUFAs) are fatty acids that contain more than one double bond in their backbone. This class includes many important compounds, such as essential fatty acids and those that give drying oils their characteristic property. Polyunsaturated fatty acids can be classified in various groups by their chemical structure: * methylene-interrupted polyenes * conjugated fatty acids * other PUFAs Based on the length of their carbon backbone, they are sometimes classified in two groups: * short chain polyunsaturated fatty acids (SC-PUFA), with 18 carbon atoms * long-chain polyunsaturated fatty acids (LC-PUFA) with 20 or more carbon atoms Dietary sources Types Methylene-interrupted polyenes These fatty acids have 2 or more ''Cis-trans isomerism, cis'' double bonds that are separated from each other by a single methylene bridge (--). This form is also sometimes called a ''divinylmethane pattern''. The essential fatty acids are all omega-3 and -6 methylene-i ...
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Fatty Acids
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 (up to 70% by weight) 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. History The concept of fatty acid (''acide gras'') was introduced in 1813 by Michel Eugène Chevreul, though he initially used some variant terms: ''graisse acide'' and ''acide huileux'' ("acid fat" and "oily acid"). Types of fatty acids Fatty acids are classified in many ways: by length, by saturation vs unsatura ...
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Docosapentaenoic Acid
Docosapentaenoic acid (DPA) designates any straight chain 22:5 fatty acid, that is a straight chain open chain type of 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 (i.e. 4''Z'',7''Z'',10''Z'',13''Z'',16''Z''-docosapentaenoic acid) and ''all''-''cis''-7,10,13,16,19-docosapentaenoic acid (i.e. 7''Z'',10''Z'',13''Z'',16''Z'',19''Z''-docosapentaenoic acid). They are also commonly termed n-6 DPA and n-3 DPA, respectively; these designations describes 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 ...
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Omega-9 Fatty Acid
Omega-9 fatty acids (ω−9 fatty acids or ''n''−9 fatty acids) are a family of unsaturated fatty acids which have in common a final carbon–carbon double bond in the omega−9 position; that is, the ninth bond from the methyl end of the fatty acid. Unlike omega-3 fatty acids and omega-6 fatty acid, omega−9 fatty acids are not classed as essential fatty acids (EFA). This is both because they can be created by the human body from unsaturated fat, and are therefore not essential in the diet, and because the lack of an omega−6 double bond keeps them from participating in the reactions that form the eicosanoids. Background Some omega−9 fatty acids are common components of animal fat and vegetable oil. Two omega−9 fatty acids important in industry are: * Oleic acid (18:1, ''n''−9), which is a main component of olive oil, macadamia oil and other monounsaturated fats * Erucic acid (22:1, ''n''−9), which is found in rapeseed, wallflower seed, and mustard seed. Rapes ...
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Docosatetraenoic 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 name adrenic acid (AdA). This is a naturally occurring polyunsaturated fatty acid formed through a 2-carbon chain elongation of arachidonic acid. It is one of the most abundant fatty acids in the early human brain. This unsaturated fatty acid is also metabolized by cells to biologically active products viz., dihomoprostaglandins, and epoxydocosatrienoic acids (EDTs, also known as dihomo-EETs). In addition to being endothelium-derived hyperpolarizing factors, EDTs have demonstrated anti-endoplasmic reticulum stress and anti-nociceptive activities. They are hydrolyzed by the soluble epoxide hydrolase (sEH) to dihydroxydocosatrienoic acids (DHDTs) and hence might play a role in the efficacy of sEH inhibitors. See also *Polyunsaturated fatty ...
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Arachidonic Acid
Arachidonic acid (AA, sometimes ARA) is a polyunsaturated omega-6 fatty acid 20:4(ω-6), or 20:4(5,8,11,14). It is structurally related to the saturated arachidic acid found in cupuaçu butter. Its name derives from the New Latin word ''arachis'' (peanut), but peanut oil does not contain any arachidonic acid. Chemistry In chemical structure, arachidonic acid is a carboxylic acid with a 20-carbon chain and four ''cis''-double bonds; the first double bond is located at the sixth carbon from the omega end. Some chemistry sources define 'arachidonic acid' to designate any of the eicosatetraenoic acids. However, almost all writings in biology, medicine, and nutrition limit the term to ''all cis''-5,8,11,14-eicosatetraenoic acid. Biology Arachidonic acid is a polyunsaturated fatty acid present in the phospholipids (especially phosphatidylethanolamine, phosphatidylcholine, and phosphatidylinositides) of membranes of the body's cells, and is abundant in the brain, muscles, an ...
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Eicosadienoic Acid
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 107-93-7. 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. 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. C15H29 ...
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Linoleic Acid
Linoleic acid (LA) is an organic compound with the formula COOH(CH2)7CH=CHCH2CH=CH(CH2)4CH3. Both alkene groups are cis-trans isomerism, ''cis''. It is a fatty acid sometimes denoted 18:2 (n-6) or 18:2 ''cis''-9,12. A linoleate is a salt (chemistry), salt or ester of this acid. Linoleic acid is a polyunsaturated fatty acid, polyunsaturated omega-6 fatty acid. It is a colorless liquid that is virtually insoluble in water but soluble in many organic solvents. It typically occurs in nature as a triglyceride (ester of glycerol, glycerin) rather than as a free fatty acid. It is one of two essential fatty acids for humans, who must obtain it through their diet, and the most essential, because the body uses it as a base to make the others. The word "linoleic" derives from the Latin ''linum'' "flax" + ''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 l ...
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Omega-6 Fatty Acid
Omega-6 fatty acids (also referred to as ω-6 fatty acids or ''n''-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. Health effects One review found that an increased intake of omega‐6 fatty acids has been shown to reduce total serum cholesterol and may reduce myocardial infarction. The same review found no significant change in LDL cholesterol and triglycerides. A 2021 review found that omega 6 supplements do not affect the risk of CVD morbidity and mortality. Dietary sources Dietary sources of omega-6 fatty acids include: * poultry * eggs * nuts * hulled sesame seeds * cereals * durum wheat * whole-grain breads * pumpkin seeds * hemp seeds Vegetable oils Vegetable oils are a major source of omega-6 linoleic acid. Worldwide, more than 100 million metric tons of vegetable oils are extracted annually from palm fruits, soybean ...
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