18.4 Chemical properties of fats and oils

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Presentation transcript:

18.4 Chemical properties of fats and oils 1. Hydrolysis Reverse of esterification Forms carboxylic acids (FAs) and alcohol (glycerol) Catalyst = acid or enzyme (lipase)

Chemical reactions of TAGs 2. Saponification (hydrolysis in base) Forms carboxylic acid salts (soaps) Na+ = hard soap; K+ = liquid soap

Chemical reactions of TAGs 3. Hydrogenation Unsaturated chains add H2 (become “hydrogenated”) Increase the melting point (become semi-solid) Side effect = production of trans fats

Olestra Artificial, noncaloric fat substitute (indigestible) FDA warning “This Product Contains Olestra. Olestra may cause abdominal cramping and loose stools. Olestra inhibits the absorption of some vitamins and other nutrients. Vitamins A, D, E, and K have been added.”

Reaction map for triglycerides

18.5 Waxes Esters of fatty acids Alcohol has long chain Insoluble in water Not easily hydrolyzed Natural protective coatings on plants, fruit, skin, fur, feathers Commercially used as candles, cosmetics

Membrane/structural lipids 18.6 Phospholipids (phosphoglycerides) 18.7 Sphingolipids (sphingomyelins and glycolipids)

18.8 Biological membranes Separate contents of cells from external fluids Semipermeable Nutrients enter, waste products leave Lipid bilayer = structural lipids and cholesterol

Fluid-mosaic model

18.9 Steroids Ex: Cholesterol, hormones 4 ring structure

Cholesterol Contains –OH Produced by liver Supplied by diet Precursor for hormones, vitamin D Component of cell membranes Provide rigidity High levels Gallstones Deposits on arteries

18.10 Steroid hormones Chemical messengers carried through the blood Same 4-ring structure as cholesterol Examples: Cortisol: increase glucose concentration in the body Cortisone: anti-inflammatory (arthritis, asthma) Testosterone, estradiol, estrone, progesterone: sex hormones

18.11 Prostaglandins Hormones involved in production of pain, fever, inflammatory reactions Synthesized from arachidonic acid (a polyunsaturated FA) Synthesis inhibited by NSAIDs e.g. acetylsalicylic acid (aspirin)

Summary of lipids