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O Pt
+3H2
CH2 O C (CH2)7CH CH(CH2)7CH3 O
O
CH2 O C (CH2)16CH3
CH O C (CH2)7CH CH(CH2)7CH3 O
O
CH O C (CH2)16CH3
CH2 O C (CH2)7CH CH(CH2)7CH3 O
CH2 O C (CH2)16CH3
Cis and Trans Unsaturated Fatty Acids
• Natural unsaturated fatty acids have cis double bonds
• When unsaturated vegetable oils are hydrogenated to form
more saturated oils (as in margarine), some of the cis fatty
acids are isomerized to trans fatty acids
• Trans fatty acids are much more linear than cis fatty acids, so
their melting points are higher and studies have shown that
trans fats may act similarly to saturated fats and could
contribute to heart disease and some cancers
• Due to new requirements for including amounts of trans fats
on food labels, many companies are developing hydrogenation
methods that do not produce trans fats
Oxidation of Unsaturated Oils
• Fats and oils can become rancid in two ways:
- bacterial ester hydrolysis (next slide)
- air oxidation of alkenes
• Oxidation of fatty acid alkenes involves cleavage of the double
bonds to form short-chain carboxylic acids
• These oxidation products are foul-tasting and smell horrible
OH
O2 or O 3
O O O
+
OH HO OH
Hydrolysis of Fats and Oils
• Fats and oils contain ester groups which can be hydrolyzed
with aqueous acid, aqueous base (saponification) or enzymes
• The hydrolysis products are glycerol and three fatty acids
• When triacylglycerols containing short-chain fatty acids are
hydrolyzed the carboxylic acid products (such as butanoic and
hexanoic acids) are foul-smelling and foul-tasting (rancid)
O
H 2C OH
H 2C O C (CH2)14CH3 O
O
H3O+
or
HC OH + 3 HO C (CH2)14CH3
HC O C (CH2)14CH3
O lipase
H 2C OH
H 2C O C (CH2)14CH3
Saponification
• When a triacylglycerol is hydrolyzed with a strong base the
process is called saponification
• The products of saponification are glycerol and fatty acid salts
(soap)
- NaOH is used with saturated fats to produce hard soaps
- KOH is used with unsaturated fats to produce softer, more
liquid soaps
H 2C O C (CH2)14CH3 H 2C OH
O O
NaOH
HC O C (CH2)14CH3 HC OH + 3 Na O C (CH2)14CH3
O
(Soap)
H 2C O C (CH2)14CH3 H 2C OH