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)

1
 Chemical reactions of TAGs

2. Saponification (hydrolysis in base)

– Forms carboxylic acid salts (soaps)
– Na+ = hard soap; K+ = liquid soap

2
 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

3
 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.”

4
Reaction map for triglycerides

5
 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

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

7
 18.8 Biological membranes
• Separate contents of cells from external fluids
• Semipermeable
– Nutrients enter, waste products leave
• Lipid bilayer = structural lipids and cholesterol

8
Fluid-mosaic model

9
 18.9 Steroids
• Ex: Cholesterol, hormones
• 4 ring structure

10
 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

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 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
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 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)

13
Summary of lipids

14