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H3C — C — C — C — C—C — C — C — C=C — C — C — C—C — C — C — C — C

Oleate

(ionized form of oleic acid)

▲ FIGURE 2-18 The effect of a double bond on the shape of fatty acids. Shown are space-filling models and chemical structures of the ionized form of palmitic acid, a saturated fatty acid with 16 C atoms, and oleic acid, an unsaturated one with

18 C atoms. In saturated fatty acids, the hydrocarbon chain is often linear; the cis double bond in oleate creates a rigid kink in the hydrocarbon chain. [After L. Stryer, 1994, Biochemistry, 4th ed., W. H. Freeman and Company, p. 265.]

If the acyl groups are long enough, these molecules are insoluble in water even though they contain three polar ester bonds. Fatty acyl groups also form the hydrophobic portion of phospholipids, which we discuss next.

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