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3: Lipids

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  • The lipids are a large and diverse group of naturally occurring organic compounds that are related by their solubility in nonpolar organic solvents (e.g., ether, chloroform, acetone and benzene) and general insolubility in water. There is great structural variety among the lipids, as will be demonstrated in the following sections.

    • 3.1: Prelude to Lipids
      Lipids are not defined by the presence of specific functional groups, as carbohydrates are, but by a physical property—solubility. Compounds isolated from body tissues are classified as lipids if they are more soluble in organic solvents, such as dichloromethane, than in water. Hence, the lipid category includes not only fats and oils, which are esters of the trihydroxy alcohol glycerol and fatty acids, but also compounds derived from phosphoric acid, carbohydrates,  amino alcohols and steroids.
    • 3.2: Fatty Acids
      Fatty acids are carboxylic acids that are the structural components of many lipids. They may be saturated or unsaturated. Most fatty acids are unbranched and contain an even number of carbon atoms. Unsaturated fatty acids have lower melting points than saturated fatty acids containing the same number of carbon atoms.
    • 3.3: Fats and Oils
      Fats and oils are composed of molecules known as triglycerides, which are esters composed of three fatty acid units linked to glycerol. An increase in the percentage of shorter-chain fatty acids and/or unsaturated fatty acids lowers the melting point of a fat or oil. The hydrolysis of fats and oils in the presence of a base makes soap and is known as saponification. Double bonds present in unsaturated triglycerides can be hydrogenated to convert oils (liquid) into margarine (solid).
    • 3.4: Waxes
      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.
    • 3.5: Membrane Lipids- Phosphoglycerides and Spingholipids
      Lipids are important components of biological membranes. These lipids have dual characteristics: part of the molecule is hydrophilic, and part of the molecule is hydrophobic. Membrane lipids may be classified as phospholipids, glycolipids, and/or sphingolipids. Proteins are another important component of biological membranes. Integral proteins span the lipid bilayer, while peripheral proteins are more loosely associated with the surface of the membrane.
    • 3.6: Saponification of Fats and Oils; Soaps and Detergents
      Soaps are the carboxylate salts of fatty acids, while detergents are sulfonate salts with long hydrocarbon tails.
    • 3.7: Steroids
      Steroids have a four-fused-ring structure and have a variety of functions. Cholesterol is a steroid found in mammals that is needed for the formation of cell membranes, bile acids, and several hormones. Bile salts are secreted into the small intestine to aid in the digestion of fats.
    • 3.8: Prostaglandins and other Eicosanoids
      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.

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