A very-long-chain fatty acid (VLCFA) is a

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, ...

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 Adrenoleukodystrophy (ALD) is a disease linked to the X chromosome. It is a result of fatty acid buildup caused by peroxisomal fatty acid beta oxidation which results in the accumulation of very long chain fatty acids in tissues throughout the b ...

and

Zellweger syndrome Zellweger syndrome is a rare congenital disorder characterized by the reduction or absence of functional peroxisomes in the cells of an individual. It is one of a family of disorders called Zellweger spectrum disorders which are leukodystrophies ...

, can be associated with an accumulation of VLCFAs. Enzymes that produce VLCFAs are the targets of herbicides including

pyroxasulfone Pyroxasulfone is a pre-emergence herbicide that inhibits the production of very long chain fatty acids in plants. The structure of the existing herbicide thiobencarb served as the basis for development but pyroxasulfone requires a lower dose (100 ...

Major VLCFAs

Some of the more common saturated VLCFAs:

lignoceric acid Lignoceric acid, or tetracosanoic acid, is the saturated fatty acid with formula C23H47COOH. It is found in wood tar, various cerebrosides, and in small amounts in most natural fats. The fatty acids of peanut oil contain small amounts of lignoc ...

(C24),

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. ...

(C26),

montanic acid Montanic acid is a saturated fatty acid isolated and detected mainly in montan wax. It also occurs in beeswax and Chinese wax. Montanic acid ethylene glycol esters and glycerol esters are used as protective layer on fruit skins and coating on foo ...

(C28),

melissic acid Melissic acid (or triacontanoic acid) is the organic compound with the formula CH3(CH2)28CO2H. It is classified as a very long chain fatty acid, a subset of saturated fatty acids. It is a white solid that is soluble in organic solvents. Melissic ...

(C30),

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 ...

(C32),

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 ...

(C34), and the

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 consti ...

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, ...

(C35). Several monounsaturated VLCFAs are also known:

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 s ...

(Δ15-24:1), ximenic acid (Δ17-26:1), and lumequeic acid (Δ21-30:1).

References

Bibliography

* Fatty acids {{chemistry-stub