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Types of Lipids
Fatty Acids
Fats, and Oils
Chemical Properties of Triglycerides
1
Types of Lipids
• Lipids with fatty acids
Waxes
Fats and oils (trigycerides)
Phospholipids
Sphingolipids
COOH
palmitic acid, a saturated acid
COOH
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
Learning Check L1
How would the melting point of stearic
acid compare to the melting points of oleic
acid and linoleic acid? Assign the melting
points of –17°C, 13°C, and 69°C to the
correct fatty acid. Explain.
stearic acid (18 C) saturated
oleic acid (18 C) one double bond
linoleic acid (18 C) two double bonds
8
Solution L1
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
14
Hydrogenation
O
CH 2 O C (CH 2)5CH CH(CH 2)7CH3
O
Ni
CH O C (CH 2)5CH CH(CH 2)7CH 3 + 3 H2
O
CH2 O C (CH 2)5CH CH(CH 2)7CH 3
15
Product of Hydrogenation
O
CH2 O C (CH 2)14CH 3
O
CH O C (CH 2)14CH 3
O
CH2 O C (CH 2)14CH 3
CH2 OH 17
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
18
Saponification
O
CH2 O C (CH 2)16CH3
O
CH O C (CH 2)16CH3 + 3 NaOH
O
CH 2 O C (CH2)16CH3
CH2 OH O
+-
CH OH + 3 Na O C (CH 2)14CH3
salts of fatty acids (soaps)
CH2 OH
19
Learning Check L3
What are the products obtained from the
complete hydrogenation of glyceryl
trioleate?
20
Solution L3
What are the products obtained from the
complete hydrogenation of glyceryl
trioleate?
2. Glyceryltristearate
21