Chapter 10.1: Storage Lipids

CHEM 7784

Biochemistry

Professor Bensley

CHAPTER 10.1 Storage Lipids

– Biological roles of lipids – Structure and properties of storage lipids

Chapter Objectives: To understand the

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

common name IUPAC name melting point (Co)

12:0 laurate dodeconoate 44

14:0 myristate tetradeconoate 52

16:0 palmitate hexadeconoate 63

18:0 stearate octadeconoate 70

20:0 arachidate eicosanoate 75

22:0 behenate docosanoate 81

24:0 lignocerate tetracosanate 84

Common Unsaturated Fatty Acids

common name IUPAC namemelting point

(Co)

16:0 palmitate hexadeconoate 63

16:1 9 palmitoleate cis-9-hexadeconoate -0.5

18:0 stearate octadeconoate 70

18:1 9 oleate cis-9- octadeconoate 13

18:2 9,12 linoleate cis-9,12- octadeconoate -9

18:3 9,12,15 linolenate cis-9,12,15- octadeconoate -17

20:0 arachidate eicosanoate 75

20:4 5,8,11,14 arachindonate cis- 5,8,11,14-eicosatetraenoate -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

70o C 13o C -17o 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