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Lipids

Lipids

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Published by Imran Sheriff

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Published by: Imran Sheriff on May 17, 2012
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Lipids

Types of Lipids Fatty Acids Fats, and Oils Chemical Properties of Triglycerides

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Types of Lipids • Lipids with fatty acids Waxes Fats and oils (trigycerides) Phospholipids Sphingolipids • Lipids without fatty acids Steroids 2 .

Fatty Acids • • • • Long-chain carboxylic acids Insoluble in water Typically 12-18 carbon atoms (even number) Some contain double bonds corn oil contains 86% unsaturated fatty acids and 14% saturated fatty acids 3 .

Saturated and Unsaturated Fatty Acids Saturated = C–C bonds Unsaturated = one or more C=C bonds COOH palmitic acid. a saturated acid COOH palmitoleic acid. an unsaturated fatty acid 4 .

Structures Saturated fatty acids • Fit closely in regular pattern COOH COOH COOH Unsaturated fatty acids H • Cis double bonds H C C cis double bond COOH 5 .

Properties of Saturated Fatty Acids • Contain only single C–C bonds • Closely packed • Strong attractions between chains • High melting points • Solids at room temperature 6 .

Properties of Unsaturated Fatty Acids • Contain one or more double C=C bonds • Nonlinear chains do not allow molecules to pack closely • Few interactions between chains • Low melting points • Liquids at room temperature 7 .

Fats and Oils Formed from glycerol and fatty acids O CH2 OH CH CH2 OH OH + HO C O (CH2)14CH3 HO C (CH2)14CH3 O HO C (CH2)14CH3 glycerol palmitic acid (a fatty acid) 8 .

Triglycerides (triacylglcerols) Esters of glycerol and fatty acids ester bonds O CH2 CH CH2 O O O C O C (CH2)14CH3 O C + H2O H 2O 9 (CH2)14CH3 + H2O (CH2)14CH3 + .

Learning Check L2 What are the fatty acids in the following triglyceride? O CH2 CH CH2 O O O C O C (CH2)7CH CH(CH2)7CH3 O C (CH2)12CH3 10 (CH2)16CH3 .

Solutions L2 What are the fatty acids in the following triglyceride? O CH2 CH CH2 O O C O (CH2)16CH3 Stearic acid Oleic acid C (CH2)7CH CH(CH2)7CH3 O Myristic acid O C (CH2)12CH3 11 .

Properties of Triglycerides Hydrogenation • Unsaturated compounds react with H2 • Ni or Pt catalyst • C=C bonds C–C bonds Hydrolysis • Split by water and acid or enzyme catalyst • Produce glycerol and 3 fatty acids 12 .

Hydrogenation O CH 2 CH CH2 O O O C O C (CH 2)5CH CH(CH 2)7CH 3 O C (CH 2)5CH CH(CH 2)7CH 3 + 3 H2 (CH 2)5CH CH(CH 2)7CH3 Ni 13 .

The solid products are used to make margarine and other hydrogenated items.Product of Hydrogenation O CH2 CH CH2 O O O C O C (CH 2)14CH 3 O C (CH 2)14CH 3 (CH 2)14CH 3 Hydrogenation converts double bonds in oils to single bonds. 14 .

Hydrolysis Triglycerides split into glycerol and three fatty acids (H+ or enzyme catalyst) O C O CH CH2 O O C (CH2)14CH3 O C (CH2)14CH3 CH2 OH CH CH2 OH OH + O 3 HO C (CH2)14CH3 15 CH2 O (CH2)14CH3 H +3 H2O + .

Saponification and Soap • Hydrolysis with a strong base • Triglycerides split into glycerol and the salts of fatty acids • The salts of fatty acids are “soaps” • KOH gives softer soaps 16 .

Saponification O CH2 CH CH 2 O O O C O C O C (CH 2)16CH3 + 3 NaOH (CH2)16CH3 CH2 OH CH CH2 (CH 2)16CH3 O +OH + 3 Na O C (CH 2)14CH3 salts of fatty acids (soaps) OH 17 .

Learning Check L3 What are the products obtained from the complete hydrogenation of glyceryl trioleate? (1) Glycerol and 3 oleic acids (2) Glyceryltristearate (3) Glycerol and 3 stearic acids 18 .

Glyceryltristearate 19 .Solution L3 What are the products obtained from the complete hydrogenation of glyceryl trioleate? 2.

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