Chapter 10.1: Storage Lipids

CHEM 7784 Biochemistry Professor Bensley

CHAPTER 10.1

Storage Lipids

Chapter Objectives

: To understand the – Biological roles of lipids – Structure and properties of storage lipids

Lipids: Structurally Diverse Class • Low solubility in water • Good solubility in nonpolar solvents

Classification of Lipids Based on the structure and function: 1.

Lipids that contain fatty acids (complex lipids): Storage lipids and membrane lipids 2.

Lipids that do not contain fatty acids: Cholesterol, terpenes , …

Lipid Subclasses

Fatty Acids • Carboxylic acids with hydrocarbon chains containing from 4 to 36 carbons • Almost all natural fatty acids have an even number of carbons • Most natural fatty acids are unbranched • Saturated: • Monounsaturated: • Polyunsaturated:

Common Saturated Fatty Acids 12:0 14:0 16:0 18:0 20:0 22:0 24:0 common name laurate myristate palmitate stearate arachidate behenate lignocerate IUPAC name dodeconoate tetradeconoate hexadeconoate octadeconoate eicosanoate docosanoate tetracosanate melting point (C o ) 44 52 63 70 75 81 84

Common Unsaturated Fatty Acids common name IUPAC name 16:0 16:1 D 9 18:0 18:1 D 9 18:2 D 9,12 18:3 D 9,12,15 20:0 20:4 D 5,8,11,14 palmitate palmitoleate stearate oleate linoleate linolenate arachidate arachindonate hexadeconoate cis D 9 -hexadeconoate octadeconoate cis D 9 - octadeconoate cis D 9,12 - octadeconoate cis D 9,12,15 - octadeconoate eicosanoate cis D 5,8,11,14 eicosatetraenoate melting point (C o ) 63 -0.5

70 13 -9 -17 75 -49

Physical Properties and Conformation of Saturated Fatty Acids • Solubility decreases as the chain length increases • Melting point increases as the chain length increases • The saturated chain tends to adopt extended conformations • The double bonds in natural unsaturated fatty acids are commonly in cis configuration • This introduces a kink in the chain

Melting Point and Double Bonds • Saturated fatty acids pack in a fairly orderly way – extensive favorable interactions • Unsaturated cis fatty acid pack less regular due to the kink – Less extensive favorable interactions • It takes less thermal energy to disrupt disordered packing of unsaturated fatty acids: – unsaturated cis fatty acids have a lower melting point

Melting Points of Fatty Acids

18:0 18:1 18:3 70 o C 13 o C -17 o C

Trans Fatty Acids • Trans fatty acids form by partial dehydrogenation of unsaturated fatty acids • A trans double bond allows a given fatty acid to adopt an extended conformation • Trans fatty acids can pack more regularly, and show higher melting points than cis forms

Triacylglycerols (fats and oils) • Majority of fatty acids in biological systems are found in the form of triacylglycerols • Triacylglycerols are the primary storage form of lipids ( body fat ) • Triacylglycerols are less soluble in water than fatty acids due to the lack of charged carboxylate group • Triacylglycerols are less dense than water: fats and oils float

Waxes • Waxes are esters of long-chain saturated and unsaturated fatty acids with long-chain alcohols • Insoluble and have high melting points • Beeswax is a mixture of a large number of lipids, including esters of triacontanol, and a long-chain alkane hentiacontane