Very Long-chain Fatty Acid
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Very Long-chain Fatty Acid
A very-long-chain fatty acid (VLCFA) is a fatty acid with 22 or more carbons. Their biosynthesis occurs in the endoplasmic reticulum. VLCFA's can represent up to a few percent of the total fatty acid content of a cell. Unlike most fatty acids, VLCFAs are too long to be metabolized in the mitochondria, in the endoplasmic reticulum (ER) in plants and must be metabolized in peroxisomes. Certain peroxisomal disorders, such as adrenoleukodystrophy and Zellweger syndrome, can be associated with an accumulation of VLCFAs. Enzymes that produce VLCFAs are the targets of herbicides including pyroxasulfone. Major VLCFAs Some of the more common saturated VLCFAs: lignoceric acid (C24), cerotic acid (C26), montanic acid (C28), melissic acid (C30), lacceroic acid (C32), ghedoic acid (C34), and the odd-chain fatty acid ceroplastic acid (C35). Several monounsaturated VLCFAs are also known: nervonic acid (Δ15-24:1), ximenic acid (Δ17-26:1), and lumequeic acid (Δ21-30:1). See also * ...
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Fatty 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 (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 unsaturati ...
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Ghedoic Acid
Geddic acid, or tetratriacontanoic acid, is a 34-carbon-long carboxylic acid and saturated fatty acid. It occurs in cotton, carnauba, candelilla wax, and in ghedda wax (wild beeswax), from which its common name is derived. See also * List of carboxylic acids * List of saturated fatty acids * Very long chain fatty acid A very-long-chain fatty acid (VLCFA) is a fatty acid with 22 or more carbons. Their biosynthesis occurs in the endoplasmic reticulum. VLCFA's can represent up to a few percent of the total fatty acid content of a cell. Unlike most fatty acids, VL ... References Alkanoic acids Fatty acids {{organic-compound-stub ...
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Cerotic Acid
Cerotic acid, or hexacosanoic acid, is a 26-carbon long-chain saturated fatty acid with the chemical formula CH3(CH2)24COOH. It is most commonly found in beeswax and carnauba wax. It is a white solid, although impure samples appear yellowish. The name is derived from the Latin word ''cerotus'', which in turn was derived from the Ancient Greek word κηρός (keros), meaning beeswax or honeycomb. Cerotic acid is also a type of very long chain fatty acid that is often associated with the disease adrenoleukodystrophy, which involves the excessive saturation of unmetabolized fatty acid chains, including cerotic acid, in the peroxisome. See also *List of saturated fatty acids *Very long chain fatty acids A very-long-chain fatty acid (VLCFA) is a fatty acid with 22 or more carbons. Their biosynthesis occurs in the endoplasmic reticulum. VLCFA's can represent up to a few percent of the total fatty acid content of a cell. Unlike most fatty acids, VL ... References Fatty acids ...
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SLC27A5
Bile acyl-CoA synthetase is an enzyme that in humans is encoded by the ''SLC27A5'' gene. The protein encoded by this gene is an isozyme of very long-chain acyl-CoA synthetase (VLCS). It is capable of activating very long-chain fatty-acids containing 24- and 26-carbons. It is expressed in liver and associated with endoplasmic reticulum but not with peroxisome A peroxisome () is a membrane-bound organelle, a type of microbody, found in the cytoplasm of virtually all eukaryotic cells. Peroxisomes are oxidative organelles. Frequently, molecular oxygen serves as a co-substrate, from which hydrogen pero ...s. Its primary role is in fatty acid elongation or complex lipid synthesis rather than in degradation. This gene has a mouse ortholog. See also * Solute carrier family References Further reading * * * * * * * Solute carrier family {{gene-19-stub ...
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SLC27A2
Very long-chain acyl-CoA synthetase is an enzyme that in humans is encoded by the ''SLC27A2'' gene. The protein encoded by this gene is an isozyme of long-chain fatty-acid-coenzyme A ligase family. Although differing in substrate specificity, subcellular localization, and tissue distribution, all isozymes of this family convert free long-chain fatty acids into fatty acyl-CoA esters, and thereby play a key role in lipid biosynthesis and fatty acid degradation. This isozyme activates long-chain, branched-chain and very long chain fatty acids containing 22 or more carbons to their CoA derivatives. It is expressed primarily in liver and kidney, and is present in both endoplasmic reticulum and peroxisomes but not in mitochondria. Its decreased peroxisomal enzyme activity is in part responsible for the biochemical pathology in X-linked adrenoleukodystrophy Adrenoleukodystrophy (ALD) is a disease linked to the X chromosome. It is a result of fatty acid buildup caused by peroxisomal fatt ...
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ACADVL
Very long-chain specific acyl-CoA dehydrogenase, mitochondrial (VLCAD) is an enzyme that in humans is encoded by the ACADVL gene. Mutations in the ACADVL are associated with very long-chain acyl-coenzyme A dehydrogenase deficiency. The protein encoded by this gene is targeted to the inner mitochondrial membrane, where it catalyzes the first step of the mitochondrial fatty acid beta-oxidation pathway. This acyl-Coenzyme A dehydrogenase is specific to long-chain and very-long-chain fatty acids. A deficiency in this gene product reduces myocardial fatty acid beta-oxidation and is associated with cardiomyopathy. Alternative splicing results in multiple transcript variants encoding different isoforms. Structure The ACADVL gene contains 20 exons, and is about 5.4 kb long. VLCAD has interesting gene structure in humans, in that is located in a head-to-head structure with the DLG4 gene on Chromosome 17, and that the transcribed regions of these genes overlap. It has been shown that ...
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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 ''wikt:nervus, nervus'', meaning nerve or sinew. It exists in nature as an elongation product of oleic acid (18:1 Δ9), its immediate precursor being erucic acid. Nervonic acid is particularly abundant in the white matter of animal brains and in peripheral nervous tissue where nervonyl sphingolipids are enriched in the myelin sheath of nerve fibers. In the same way, recent studies have concluded that nervonic acid is implicated as an intermediate in the biosynthesis of nerve cell myelin. This acid is an important member of the group of the cerebrosides, which are fatty acids of the glycosphingolipids group, important components of the muscles and the central nervous system and peripheral. Indeed, it is one of the major fatty acids in brain sphingolipids, normally accou ...
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Ceroplastic Acid
Ceroplastic acid (or pentatriacontanoic acid) is a saturated aliphatic carboxylic acid. The name is derived from the Latin word ''cerotus'', which in turn was derived from the Ancient Greek word κηρός (keros), meaning beeswax or honeycomb, combined with "plastic" from the Latin plasticus (meaning of molding, from Greek plastikos, from plassein to mold, form). Applications Like many other carboxylic acids, ceroplastic acid can react with UV curable moiety alcohols to form reactive esters, such as 2-allyloxyethanol. See also *List of saturated fatty acids See also * List of unsaturated fatty acids *Carboxylic acid **List of carboxylic acids *Dicarboxylic acid {{DEFAULTSORT:List Of Saturated Fatty Acids Saturated Fatty Acids A saturated fat is a type of fat in which the fatty acid chains ... References External linksCeroplastic acidat the ''Nature Lipidomics Gateway'' Fatty acids Alkanoic acids {{organic-compound-stub ...
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Odd-chain Fatty Acid
Odd-chain fatty acids are those fatty acids that contain an odd number of carbon atoms. In addition to being classified according to their saturation or unsaturation, fatty acids are also classified according to their odd or even numbers of constituent carbon atoms. With respect to natural abundance, most fatty acids are even chain, e.g. palmitic (C16) and stearic (C18). In terms of physical properties, odd and even fatty acids are similar, generally being colorless, soluble in alcohols, and often somewhat oily. The odd-chain fatty acids are biosynthesized and metabolized slightly differently from the even-chained relatives. In addition to the usual C12-C22 long chain fatty acids, some very long chain fatty acids (VLCFAs) are also known. Some of these VLCFAs are also of the odd-chain variety. Biosynthesis The most common OCFA are the saturated C15 and C17 derivatives, respectively pentadecanoic acid and heptadecanoic acid. The synthesis of even-chained fatty acid synthesis is ...
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Lacceroic Acid
Lacceroic acid (or dotriacontanoic acid) is a saturated fatty acid. Sources Lacceroic acid can be derived by saponification of lacceryl lacceroate or by oxidation of 1-Dotriacontanol (lacceryl) and purification of the product. It can also be isolated from stick lac wax, from which the name is derived. Derivatives Ethyl lacceroate can be obtained as a crystalline solid (rhombic plates, mp 76 °C) by the action of HCl gas on lacceroic acid in boiling absolute alcohol. See also *List of saturated fatty acids See also *List of unsaturated fatty acids *Carboxylic acid **List of carboxylic acids *Dicarboxylic acid {{DEFAULTSORT:List Of Saturated Fatty Acids Saturated Fatty Acids A saturated fat is a type of fat in which the fatty acid chains ... References External linksLacceroic acidat the ''Nature Lipidomics Gateway'' Fatty acids Alkanoic acids {{organic-compound-stub ...
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