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The biosynthesis of oleic acid involves the action of the enzyme stearoyl-CoA 9-desaturase acting on stearoyl-CoA. In effect, stearic acid is dehydrogenated to give the monounsaturated derivative, oleic acid. [6] Oleic acid undergoes the typical reactions of carboxylic acids and alkenes. It is soluble in aqueous base to give soaps called ...
It is formed from the precursor oleic acid (a monounsaturated fatty acid). [29] After oleic acid is esterified to a phospholipid, S-adenosyl-methionine donates a methyl group to the double bond of oleic acid. [30] This methylation reaction forms the intermediate 10-methylene-octadecanoyal.
Fatty acids exhibit reactions like other carboxylic acids, i.e. they undergo esterification and acid-base reactions. Fatty acids do not show a great variation in their acidities, as indicated by their respective pK a. Nonanoic acid, for example, has a pK a of 4.96, being only slightly weaker than acetic acid (4.76).
Much like beta-oxidation, straight-chain fatty acid synthesis occurs via the six recurring reactions shown below, until the 16-carbon palmitic acid is produced. [ 35 ] [ 36 ] The diagrams presented show how fatty acids are synthesized in microorganisms and list the enzymes found in Escherichia coli . [ 35 ]
The synthesis of unsaturated fatty acids involves a desaturation reaction, whereby a double bond is introduced into the fatty acyl chain. For example, in humans, the desaturation of stearic acid by stearoyl-CoA desaturase-1 produces oleic acid .
Azelaic acid and pelargonic acids are produced from ozonolysis of oleic acid on an industrial scale. An example is the ozonolysis of eugenol converting the terminal alkene to an aldehyde: [9] By controlling the reaction/workup conditions, unsymmetrical products can be generated from symmetrical alkenes: [10]
Long-chain-fatty-acid—CoA ligase catalyzes the reaction between a fatty acid with ATP to give a fatty acyl adenylate, plus inorganic pyrophosphate, which then reacts with free coenzyme A to give a fatty acyl-CoA ester and AMP. If the fatty acyl-CoA has a long chain, then the carnitine shuttle must be utilized (shown in the table below):
It can be produced by the hydrogenation of oleic acid esters by Bouveault–Blanc reduction, which avoids reduction of the C=C group (as would occur with usual catalytic hydrogenation). The required oleate esters are obtained from beef fat , fish oil , and, in particular, olive oil (from which it gains its name).
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