1. Chapter 7
Lipids

2. Lipid Subclasses

3. Fatty acids

4. Fatty acid nomenclature

5. Common saturated fatty acids
common name
IUPAC name
melting point (Co)
12:0
laurate
dodeconoate 44
14:0
myristate
tetradeconoate 52
16:0
palmitate
hexadeconoate 63
18:0
stearate
octadeconoate 70
20:0
arachidate
eicosanoate 75
22:0
behenate
docosanoate 81
24:0
lignocerate
tetracosanate 84

6. Common unsaturated fatty acids
common name
IUPAC name
melting point
(Co)
16:0
palmitate
hexadeconoate 63
16:1 D9
palmitoleate
cis-D9-hexadeconoate
-0.5
18:0
stearate
octadeconoate 70
18:1 D9
oleate
cis-D9- octadeconoate 13
18:2 D9,12
linoleate
cis-D9,12- octadeconoate -9
18:3 D9,12,15
linolenate
cis-D9,12,15- octadeconoate
-17
20:0
arachidate
eicosanoate 75
20:4 D5,8,11,14
arachindonate
cis- D5,8,11,14-eicosatetraenoate
-49

7. Physical Properties of Fatty acids
18: : :3
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Physical Properties of Fatty acids

8. Unusual fatty acids can function analogously to unsaturated fatty acids

9. Phospholipids

11. Common membrane phospholipids

12. Enzymes used to Dissect Phospholipid Structure

13. Lipids Function: energy storage cell membrane cushions organs
very concentrated
twice the energy as carbohydrates!
cell membrane
cushions organs
insulates body
think whale blubber!

14. Fatty Acids
The simplest lipids are the fatty acids, which rarely exist alone in nature, but instead are usually a component of more complex lipids
Fatty acids are carboxylic acids with a long hydrocarbon chain attached
Although the acid end is polar, the nonpolar hydrocarbon tail makes fatty acids insoluble (or sparingly soluble) in water
Fatty acids can be classified by how many double bonds are present in the hydrocarbon tail:
- Saturated fatty acids have only single bonds
- Monounsaturated fatty acids have one double bond
- Polyunsaturated fatty acids have two or more double bonds

15. Structure of Fat
not a chain (polymer) = just a “big fat molecule”

16. Structures and Melting Points of Saturated Fatty Acids

17. Saturated fats Most animal fats Limit the amount in your diet
solid at room temperature
Limit the amount in your diet
contributes to heart disease
deposits in arteries

18. Physical Properties of Saturated Fatty Acids
Saturated fatty acids have:
Molecules that fit closely together in a regular pattern
Strong attractions (dispersion forces) between fatty acid chains
High melting points that makes them solids at room temperature.

19. Structures and Melting Points of Unsaturated Fatty Acids

20. Unsaturated fats Plant, vegetable & fish fats
liquid at room temperature
the fat molecules don’t stack tightly together
Better choice in your diet

21. Physical Properties of Unsaturated Fatty Acids
Unsaturated fatty acids have:
Nonlinear chains that do not allow molecules to pack closely
Weak attractions (dispersion forces) between fatty acid chains
Low melting points and so are liquids at room
temperature

22. Saturated vs. unsaturated

23. Triacylglycerols
Triacylglycerols (also called triglycerides) are tri-fatty acid esters of glycerol
Triacylglycerols are the major form of fatty acid storage in plants and animals
Triacylglycerols can be classified as fats or oils
- fats are solid at room temperature and most come from animals
- oils are usually liquid at room temperature and come from plants (palm and coconut oils are solids at room temperature)

24. Melting Point and Fatty Acid Composition of Some Fats and Oils

25. Olive Oil
Olive oil contains mostly triolein, which has three oleic acids
Oleic acid, a monounsaturated fatty acid, is a component of all fats and oils, but is especially abundant in olive and peanut oils
Some studies have shown that oleic acid may raise HDL (“good cholesterol”) levels while also lowering LDL (“bad cholesterol”) levels

26. Olestra: a Fat Subsitute
Olestra is:
- used in foods as an artificial fat
- sucrose linked by ester bonds to several long-chain fatty chains
- not broken down in the intestinal tract
Olestra inhibits the absorbtion of fat-soluble vitamins (A, D, E and K) and carotenoids
There are many reports of problems such as diarrhea and abdominal cramps with olestra use, but the manufacturers claim there’s no proof

27. Hydrogenation of Unsaturated Oils
Hydrogenation converts alkenes to alkanes
So, hydrogenation of unsaturated oils produces saturated fats
Hydrogenation is typically carried out by bubbling H2 gas through the heated oil, in the presence of a metal catalyst (such as nickel or platinum)
Unsaturated oils are usually only partially hydrogenated, so that the product is not completely saturated, giving a soft semisolid fat such as margarine

28. 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

29. 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

30. 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)

31. 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