CHAPTER 15

LIPIDS
 REACTION OF FATS AND OILS
A) Addition reaction
i) Addition of I2

-high number of Iodin – high degree of unsaturation (double bond)

typical procedure:
- fat is mixed with wij’s solution (1,1,1-trichloroethane), then left in
the dark room.
-potasium iodide and deionized water is added
- the mixture then titrated with sodium thiosulfate.
ii) Addition of H2
- H is added to double bonds of fats and oils – saturated
glycerides
B) Oxidation Reactions
i) Rancidification
– fats and oils are exposed to air to produce
carboxylic acids – make the oils unusable.
- C=C is oxidized to carboxylic acid
- to avoid rancidification, antioxidant is added
(flavonoids, tocopherols,ascorbic acid, BHA, BHT)

ii) Drying oils

- unsaturated oil is exposed to air – hardens to a
tough through chemical polymerization
- oxygen attacks at the allylic position to form an
extremely large cross-linked polymer.
-key component of oil paint and varnishes.
c) Saponification
- alkaline hydrolysis of esters to form glycerol and salts
of the constituents fatty acids

- Soap production
 SOAPS AND DETERGENTS
Sructure of soaps ( Sodium strearate, Na+ C17H35CO2 -)

• The carboxylate – hydrophilic( water loving) and hydrocarbon tail is

hydrophobic (water fearing)
• h/c tend to cluster to minimize their contact with water, carboxylate
group remain to contact with water = micelles
• when water containing dissolved soap is mixed with oil, the
hydrocarbon tail will ‘dissolve’ the oil in the center of micelle– broken
up into small droplets and washed away in the polar wash water.
Detergent
• Posses a long, nonpolar, hydrophobic hydrocarbon chain
that is soluble in fats, oils and greases
• Posses a polar, hydrophilic end that is soluble in water
• Anionic detergents: (-ve)ly charge polar end such as
sulfonate or sulfate
• Cationic detergent – (+ve)ly charge polar end such as an
ammonium group

• Have significant germicidal properties – used in

shampoo, mouthwash, soaps disinfectant skin sprays
• Nonionic detergent- water soluble end is polar
and form hydrogen bonds with water such as
alcohol.
 BIOLIPIDS
A) Steroids – fused rings (3 six-membered rings and 1
five-membered ring)
i) Cholesterol – the precursor to all endocrine hormons
- nonsaponifiable, nonpolar lipid

cholesterol
ii) Steroid hormones

aldosterone cortisol
estrogen progesterone

testosterone
iii) Bile acids – a cholesterol derived detergent molecule,
that is secreted by the gall-bladder into the intestine to
assist in the absorption of dietary lipids

Taurocholic acid Glycocholic acid

iv) Toxins

batrachotoxin digitoxin
B) Vitamins

Vitamin E – tocopherol
Vitamin K = aid in blood clotting
- antioxidant

Vitamin D3 – facilitates the

absorption of Ca & P into
the bones
c) Pigments

Phycoerythrin – red pigment

β-carotene

Chlorophyll a
 homework
The uses of cholesterol, steroid hormones,
bile acids, toxins, vitamins and pigments.