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Berg JM, Tymoczko JL, Stryer L. Biochemistry. 5th edition. New York: W H Freeman; 2002.

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Biochemistry. 5th edition.

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Section 12.2Fatty Acids Are Key Constituents of Lipids

Among the most biologically significant properties of lipids are their hydrophobic properties. These properties are mainly due to a particular component of lipids: fatty acids, or simply fats. Fatty acids also play important roles in signal-transduction pathways (Sections 15.2 and 22.6.2).

12.2.1. The Naming of Fatty Acids

Fatty acids are hydrocarbon chains of various lengths and degrees of unsaturation that terminate with carboxylic acid groups. The systematic name for a fatty acid is derived from the name of its parent hydrocarbon by the substitution of oic for the final e. For example, the C18 saturated fatty acid is called octadecanoic acid because the parent hydrocarbon is octadecane. A C18 fatty acid with one double bond is called octadecenoic acid; with two double bonds, octadecadienoic acid; and with three double bonds, octadecatrienoic acid. The notation 18:0 denotes a C18 fatty acid with no double bonds, whereas 18:2 signifies that there are two double bonds. The structures of the ionized forms of two common fatty acids—palmitic acid (C16, saturated) and oleic acid (C18, monounsaturated)—are shown in Figure 12.2.

Image ch12fu2.jpg

Figure 12.2. Structures of Two Fatty Acids.

Figure 12.2

Structures of Two Fatty Acids. Palmitate is a 16-carbon, saturated fatty acid, and oleate is an 18-carbon fatty acid with a single cis double bond.

Fatty acid carbon atoms are numbered starting at the carboxyl terminus, as shown in the margin. Carbon atoms 2 and 3 are often referred to as α and β, respectively. The methyl carbon atom at the distal end of the chain is called the ω-carbon atom. The position of a double bond is represented by the symbol Δ followed by a superscript number. For example, cis9 means that there is a cis double bond between carbon atoms 9 and 10; trans2 means that there is a trans double bond between carbon atoms 2 and 3. Alternatively, the position of a double bond can be denoted by counting from the distal end, with the ω-carbon atom (the methyl carbon) as number 1. An ω-3 fatty acid, for example, has the structure shown in the margin. Fatty acids are ionized at physiological pH, and so it is appropriate to refer to them according to their carboxylate form: for example, palmitate or hexadecanoate.

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12.2.2. Fatty Acids Vary in Chain Length and Degree of Unsaturation

Fatty acids in biological systems usually contain an even number of carbon atoms, typically between 14 and 24 (Table 12.1). The 16- and 18-carbon fatty acids are most common. The hydrocarbon chain is almost invariably unbranched in animal fatty acids. The alkyl chain may be saturated or it may contain one or more double bonds. The configuration of the double bonds in most unsaturated fatty acids is cis. The double bonds in polyunsaturated fatty acids are separated by at least one methylene group.

Table 12.1. Some naturally occurring fatty acids in animals.

Table 12.1

Some naturally occurring fatty acids in animals.

The properties of fatty acids and of lipids derived from them are markedly dependent on chain length and degree of saturation. Unsaturated fatty acids have lower melting points than saturated fatty acids of the same length. For example, the melting point of stearic acid is 69.6°C, whereas that of oleic acid (which contains one cis double bond) is 13.4°C. The melting points of polyunsaturated fatty acids of the C18 series are even lower. Chain length also affects the melting point, as illustrated by the fact that the melting temperature of palmitic acid (C16) is 6.5 degrees lower than that of stearic acid (C18). Thus, short chain length and unsaturation enhance the fluidity of fatty acids and of their derivatives.

By agreement with the publisher, this book is accessible by the search feature, but cannot be browsed.

Copyright © 2002, W. H. Freeman and Company.
Bookshelf ID: NBK22497


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