Erucic acid (Molecule of the Month for August 2007)
Docos-13-enoic acid, Unsaturated Fatty acid
Erucic acid is a monounsaturated omega-9 fatty acid, denoted 22:1 ω-9. It is prevalent in rapeseed, wallflower seed, and mustard seed, making up 40 to 50 percent of their oils. Fatty acids are a carboxylic acid with a long unbranched aliphatic tail (chain), which is either saturated or unsaturated. Fatty acids derived from natural fats and oils may be assumed to have at least 8 carbon atoms. Most of the natural fatty acids have an even number of carbon atoms, because their biosynthesis involves acetyl-CoA, a coenzyme carrying a two-carbon-atom group.
Unsaturated fatty acids have one or more alkenyl functional groups exist along the chain. The two next carbon atoms in the chain that are bound to either side of the double bond can occur in a cis or trans configuration. A cis configuration means that adjacent carbon atoms are on the same side of the double bond. The rigidity of the double bond freezes its conformation and, in the case of the cis isomer, causes the chain to bend and restricts the conformational freedom of the fatty acid. The more double bonds the chain has in the cis configuration, the less flexibility it has. When a chain has many cis bonds, it becomes quite curved in its most accessible conformations. For example, oleic acid, with one double bond, has a "kink" in it, while linoleic acid, with two double bonds, has a more pronounced bend. Alpha-linolenic acid, with three double bonds, favors a hooked shape.The effect of this is that in restricted environments, such as when fatty acids are part of a phospholipid in a lipid bilayer, or triglycerides in lipid droplets, cis bonds limit the ability of fatty acids to be closely packed and therefore could affect the melting temperature of the membrane or of the fat. A trans configuration, by contrast, means that the next two carbon atoms are bound to opposite sides of the double bond. As a result, they don't cause the chain to bend much, and their shape is similar to straight saturated fatty acids. In most naturally occurring unsaturated fatty acids, each double bond has 3n carbon atoms after it, for some n, and all are cis bonds. Most fatty acids in the trans configuration (trans fats) are not found in nature and are the result of human processing (eg, hydrogenation). The differences in geometry between the various types of unsaturated fatty acids, as well as between saturated and unsaturated fatty acids, play an important role in biological processes, and in the construction of biological structures (such as cell membranes).
The human body can produce all but two of the fatty acids it needs. These two, linoleic acid (LA) and alpha-linolenic acid (LNA), are widely distributed in plant oils. In addition, fish oils contain the longer-chain omega-3 fatty acids eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA). Since they cannot be made in the body from other substrates and must be supplied in food, they are called essential fatty acids. Mammals lack the ability to introduce double bonds in fatty acids beyond carbon 9 and 10.Hence linoleic acid and linoleinic acid are essential fatty acids for humans. In the body, essential fatty acids are primarily used to produce hormone-like substances that regulate a wide range of functions, including blood pressure, blood clotting, blood lipid levels, the immune response, and the inflammation response to injury infection.
Formal Chemical Name (IUPAC)
Update by Karl Harrison
(Molecule of the Month for August 2007 )
All the images on this web site are are made available with a Creative Commons Attribution license and so can be used as long as the attribution © Karl Harrison 3DChem.com is written with the image. High resolution images and illustrations are available on request.