Substituent groups

In addition to the very common fatty acids with straight saturated or unsaturated acyl chains, many fatty acids are chemically modified by substituents on the hydrocarbon chain. For example, the preening gland of ducks secretes a fatty acid 10 carbons long with methyl (CH₃) groups substituted for one of the hydrogens on carbons 2, 4, 6, and 8. Some bacteria produce fatty acids that have a methyl group on the carbon atom farthest from the acidic group or on the penultimate carbon. Other bacteria incorporate a cyclopropane ring near the centre of the acyl chain. The bacterium that causes tuberculosis (Mycobacterium tuberculosis) synthesizes a whole family of cyclopropane-containing fatty acids called α-mycolic acids. Similar fatty acids are found in related bacteria. A third common constituent is a hydroxyl group (OH). Monohydroxyl acids are found in both plants and animals in relatively small amounts, but they are more prevalent in bacteria.