Lipids are naturally occurring organic compounds that can be extracted from cells and tissues using nonpolar solvents. Although many lipids have complex structures, their chemistry can often be understood quite readily by applying the basic concepts you have studied in previous chapters. We begin the chapter with a study of fats and oils, and explain the different origins of these structurally similar substances. A discussion of soaps follows, as soap is obtained by the reaction of a fat with sodium hydroxide. Phospholipids are substances whose structures are somewhat similar to those of fats, except that the former contain a phosphate group. Prostaglandins are lipids that play important roles in biological systems and are of great interest to those involved in the medical and pharmaceutical professions. Terpenoids form a series of compounds whose structural similarity can be seen through the application of the isoprene rule. The chapter concludes with a discussion of steroids, with particular attention being paid to the stereochemistry of these substances.
- 27.2: Waxes, Fats, and Oils
- Fats play an important role in human nutrition, and most people are aware of the desirability of limiting their dietary intake of saturated fats, as these compounds have been associated with heart disease. Unsaturated fats are generally considered to be much more desirable from the point of view of good health. Notice that all the fatty acids derived from naturally occurring fats have a Z (i.e., cis) configuration.
- 27.5: Prostaglandins and Other Eicosanoids
- Prostaglandins were first discovered and isolated from human semen in the 1930s by Ulf von Euler of Sweden. Thinking they had come from the prostate gland, he named them prostaglandins. It has since been determined that they exist and are synthesized in virtually every cell of the body. Prostaglandins, are like hormones in that they act as chemical messengers, but do not move to other sites, but work right within the cells where they are synthesized.
- 27.7: Steroids
- The important class of lipids called steroids are actually metabolic derivatives of terpenes, but they are customarily treated as a separate group. Steroids may be recognized by their tetracyclic skeleton, consisting of three fused six-membered and one five-membered ring.