LIPIDS

•This next section is on lipids, or fats. Some of the

things that will be covered include:
–Classes of lipids
–Structures (you will not need to memorize these)
–Digestion/Absorption/Metabolism
–Transport of lipids in the body
–Functions (of lipids in the body and in foods)
–Food Fat (different fats and the foods that they are in)
1st, let’s start with a quiz!! Lipids: True or False?
Lipids containing saturated fatty acids are solid at room temp.
TRUE (their chemical structures affect their physical properties)
Lipids yield more energy than CHO or protein.
TRUE
Cholesterol is found in both foods of plant and animal origins.
FALSE (only animal foods, but why?)
Triglycerides are the main fats found in food.
TRUE (chemical form of fat in foods and also in the body)
Fat is essential in the human diet.
TRUE (more on this later)
Hydrogenation makes vegetable oil more solid.
TRUE
Fruits & vegetables are essentially “fat free.”
TRUE Exception? (yes, there are many exceptions. Do you like avocados?)
Butter & margarine contain the same amount of fat.
TRUE (which is better, butter or margarine?)
 What is the significance? Why do
we need to discuss fat?
• Fat provides over 35% of total calories in the
typical American diet.
– WE eat a lot of fat.
• Excess FAT, in the diet and in the body, is linked
to chronic disease states such as…
– Heart Disease
– Obesity
– Cancer
• So there are many reasons why we need to discuss
fat.
Lipids
There are 3 classes of lipids:
• Triglycerides (in food and in the body)
– A triglyceride is composed of a glycerol molecule +
3 fatty acids.
– Depending on the chemical make up of the fatty
acids, the triglyceride could be primarily a
saturated, monounsaturated, or polyunsaturated fat.
• Sterols
– Cholesterol is the only sterol we will cover.
• Phospholipids
– Lecithin is a type of phospholipid that is used by
the food industry.
 Triglyceride

Notice how these 3 fatty acids line up. These are saturated fatty acids and when put into a
triglyceride, they line up very well and form a very compact structure. More later!
 Chemical features of fatty acids
• Fatty Acids
– On one end of the fatty acid is an Acid group (COOH); at the other
end is a methyl group (CH3)
• Chain length
– Usually there will be an even # of carbons, 4-24 carbons
• Saturation refers to the presence of double bonds in the
carbon chain of a fatty acid.
– Saturated 0 double bonds
– Monounsaturated 1 double bond
– Polyunsaturated 2 or more double bonds
• The level of saturation will affect the physical properties,
what the fat “looks” like at room temperature.
This is just showing the
different ends of the fatty
acid. This will be important
when we start naming fatty
acids. Have you heard of
“omega 3 fats”? The omega
designation refers to the
placement of the double bond
in relation to the “omega”
end. Simple!
 1. Notice how “straight”
the saturated fatty acid is.

2. Notice how a double

bond puts a “kink” in the
monounsaturated fatty acid.

3. Notice how 2 double bonds put

2 “kinks” the polyunsaturated
fatty acid.

Fatty Acids
 Degree of unsaturation and
physical nature of fats.
• Saturated Fats
– Saturated fats contain mostly saturated fatty acids.
– When a triglyceride is composed of saturated fatty acids,
the fatty acids line up and form a very dense, compact
structure. This makes the fat SOLID at room
temperature.
– Remember from a previous slide what a triglyceride
looks like? The picture actually showed a saturated fat.
If you go back, you will see how the fatty acids lined up.
– What are some foods that are made of saturated fats?
 Degree of unsaturation and
physical nature of fats.
• Monounsaturated Fats
– Monounsaturated fats contain mostly monounsaturated
saturated fatty acids.
– When a triglyceride is composed of monounsaturated
fatty acids, the fatty acids have “kinks” in them and do
not line up. The structure is not very dense and compact.
This makes the fat LIQUID at room temperature.
– What are some foods that contain monounsaturated fats?
• Polyunsaturated Fats
– The same holds true for polyunsaturated fats. The
“kinks” in the fatty acid chain make the polyunsaturated
fats LIQUID at room temperature also.
 Position of double bond in unsaturated fatty acids
determines group (omega 3, 6, 9 etc.)
• Naming of the fatty acid refers to the placement
of the first double bond relative to CH3 end of
fatty acid.
• Certain omega-3 and omega-6 fatty acids are
ESSENTIAL. (more later!)
HHHHHHHHH HHHHHHHH
H C-C-C-C-C-C-C-C-C=C-C-C-C-C-C-C-C-COOH n-9
HHHHHHHH HHHHHHH

This fatty acid is an omega 9; the 1st double bond is at #9 carbon.

 Examples of Fatty Acids
• Saturated:
– Butyric acid (C4): found in butterfat.
– Stearic acid (C18): found in most animal fats.
• Monounsaturated:
– Oleic acid (C18:1): found in olive oil canola oil.
• Polyunsaturated: Essential
– Linoleic acid (C18:2 n-6): found in sunflower, fatty
safflower, corn oils, soybean oil. acids
– Linolenic acid (C18:3 n-3): found in soybean oils,
canola oil, flaxseed, walnuts.
 Functions of Fat in the body!
• Fat provides ENERGY!!!
– WE store FAT as an energy reserve. It is a significant fuel source.
– FAT is the primary source of energy at rest.
• Because we have fat available for energy, our bodies can use protein
and CHO efficiently.
• Fat provides Structural materials.
– As phospholipids, it is a component of all cell membranes.
• Fat is used in the body to Regulate many things.
– It is required for absorption and transport of fat soluble vitamins.
– It is used to synthesize steroide hormones and other regulatory
compounds.
• Fat provides insulation and acts as “shock absorbers” to
cushion organs.
• FAT is very IMPORTANT in the body!!!
What about Fat’s functions in foods??

• Fat adds flavor and texture.

– Think about how removal or addition
of fat to certain foods can completely
change the flavor or texture. Milk?
Cheese? Ground Beef?
• Fat carries fat-soluble vitamins in
foods.
• Fat provides essential fatty acids.
• Fat helps to aid with satiety.
 Summary of Saturated and
Unsaturated Fats
• Saturated Fats • Unsaturated Fats
– Solid at room temperature. – Liquid at room temperature
– More stable, don’t degrade or – Less stable; susceptible to
go bad as quickly. oxidation (rancidity)
– Low in Essential Fatty Acids. – High in Essential Fatty Acids.
– These are typically fats of – These are typically fats of plant
animal origin origin.
• Butter, meats, milk • Corn oil, soybean oil, olive oil
• Exceptions: fish oils • Exceptions: coconut oil, palm
– Fish contain oil
polyunsaturated fats. – These are solid, saturated,
Makes sense doesn’t it? plant fats.
Recap: Saturated vs Unsaturated Fats
• In terms of firmness
– Usually more firm means more saturated.
• In terms of stability
– Saturated fats are less vulnerable to oxidation and have
a longer shelf life. This is great for the food industry.
• The problem, however, is that saturated fats in the
diet increase risk of heart disease!

• But, what about hydrogenated oils? These “look”

like saturated fats.
 Hydrogenated Fats
• Hydrogenation of oils is a process that adds hydrogens to the
carbons at the double bonds unsaturated oils.
• This process causes chemical and physical changes in the oil.
• It changes the oil from unsaturated to saturated; from liquid to
solid.
– By doing so, it makes the oil more resistant to oxidation or
rancidity; it has a longer shelf life.
– It also makes it have a higher melting point. This is great for
frying foods.
– However, the bad thing is that it causes some of the double
bonds in the fatty acids to switch configuration to the
“Trans” form instead of the “Cis” form. It forms trans-fatty
acids!!
 Hydrogenation of Fat

• To make hydrogenated oils:

– Take a vat of polyunsaturated oil.
– Using a metal catalyst, usually nickel or aluminum,
infuse Hydrogen gas.
– The Hydrogens bond to the carbons at the double
bonds, removing the double bonds and the “kinks”.
 Hydrogenation of Fats
• Converts an unsaturated fat to a saturated fat.
• Makes it more stable; less susceptible to oxidation
• Liquid Solid
• In the process, Essential Fatty Acids are
destroyed.
• This results in the formation of “Trans” Fats
 Hydrogenation
• Configuration of double bonds: cis vs. trans
– Cis: the predominant situation in nature; hydrogens are on the same
side of the double bond.
– Trans: mostly in “partially hydrogenated” fats/oils; smaller amount in
beef tallow, milkfat; hydrogens are on opposite sides of the double
bond.

HHH HHHHHH HHHHHHH H

H-C-C-C-C-C-C-C-C-C=C-C-C-C-C-C-C-C-COOH “cis”
HHH HHHHH HHHHHH H

HHH HHHHH HHHHHHH H

H-C-C-C-C-C-C-C-C-C=C-C-C-C-C-C-C-C-COOH “trans”
HHH HHHHHH HHHHHHH
 Cis

to
Trans

Notice how the “kink” is removed by changing the configuration of the double bond.
This makes the fatty acid “look” like a saturated fat even though it is an unsaturated
fat. That is the problem!! The body “sees” the fatty acid as if it were saturated and
responds to it, or metabolizes it, as if it were saturated.
Trans Fats in Food
• Trans-fatty acids are
found in many
different types of
snack foods!
 Trans-fatty acids in your diet.
• Make up ~5% total kCals intake in US.
• It depends on type of fat or food that you eat if you have a
significant amount of trans-fats in yoru diet.
• Typically, if you are eating a lot of fried food, pastries,
cookies, or prepared foods, you might be getting a lot of
trans-fats.
• How do you know? Check the Label!
– If “partially hydrogenated oil” appears within the first items on the
ingredients list, chances are the food contains a fair amount of
trans-fatty acids.
• There is ongoing research regarding implications of trans-
fat and heart disease.
Trans Fat Content of Foods
Food g/100g Fat
Popcorn 45.7
Crackers 40.3
Fruit roll-up 37.5
French fries 39.6
Chicken sandwich (fried) 27.1
Margarine – stick 39.8
Margarine – tub 16.8
Danish 50.5
Cookies 23.0
Tortilla 30.0
 New “Trans-Fat” Free
• Many companies that make
crackers and other snack foods
have taken the hydrogenated oil
out of their formulations.
– Exchange
• Partially hydrogenated
Soybean Oil for Soybean
Oil
– Added
• Monoglycerides
• Supermarket Sleuth: Check for
products that are trans-fat free
next time you are in the grocery
store!!
 Essential Fatty Acids
• Linoleic Acid: C18:2n6 Omega-6
– Vegetable oils, seeds, nuts, grains
– Adequate Intake 17g/d: 12g/d
• Linolenic Acid: C18:3n3 Omega-3
– Soybeans, wheat germ, canola and soybean oil
– Adequate Intake 1.6g/d: 1.1g/d
• DHA, EPA, Arachidonic Acid (not essential)
– Fatty fish (DHA, EPA), Meat (AA)
• Fatty acid deficiencies
– Rare; Neurological abnormalities, dry/scaly skin,
– Deficiencies mainly seen in infants on lowfat diets, lipid
malabsorption syndrome,or critically ill
Essential Fatty Acids: Functions
• The body uses omega 3 and omega 6 fatty acids
to synthesize Eicosanoids through a series of
desaturation and elongation reaction.
– Omega 3s
18:3n3 18:4n3 20:4n3 20:5n3 Eicosanoids
– Omega 6s
18:2n6 18:3n6 20:3n6 20:4n6 Eicosanoids
• Eicosanoids
– Hormone-like substances that have a lot of regulatory functions
in the body.
– Functions such as: Vasodilation, Vasoconstriction, Adhesion,
Contraction
– Eicosanoids include: Thromboxanes, Leukotrienes,
Prostaglandins
Pronounced: “eye – cose – an - oids”
 Phospholipids

Now let’s take a look an another type

of lipid, the phospholipid!
Phospholipids
• Phospholipids are similar structure to triglycerides in that they
have a glycerol backbone on which is attached 2 fatty acids.
Instead of a 3rd fatty acid, there is a nitrogen containing group
and a PO4 group.
• What makes the phospholipid unique is that part of the
structure likes to be in fat, and part likes to be in water.

Loves
FAT

Loves
Water
Phospholipids
• The structure of the phospholipid makes is a perfect
compound anywhere that water and fat need to interface.
• Food Industry
– Phospholipids are used by food industry as emulsifiers. For
example in making mayonnaise or hollandaise sauce.
– Found in eggs, liver, soybeans
• Human Body
– All cell membranes in the body are made of a phospholipid bilayer.
This allows fat soluble substances and water soluble substances to
pass across the membrane.
– Phospholipids are important for emulsifying fat and for
transporting fat through the blood. (more on this later)
Cell Membrane

Phospholipid
bilayer
 Sterols

Now, let’s look briefly at the sterols,

specifically Cholesterol.
Sterols
• Sterols are mutliple-ring structures that include
cholesterol, steroid hormones, vitamin D, and others.
• Cholesterol is made in liver from 2-carbon units.
– Cholesterol is ONLY found in animal products ( meats, eggs,
fish, poultry, & dairy products).
– It is a structural component of cell membranes.
– It is used in the body to synthesize
• Bile
• Steroid Hormones
• Vitamin D
– Most of the cholesterol in the body is from what your own
body makes. Diet represents a small %.
Cholesterol Vitamin D

Notice how they are similar in structure!

 Bile Acid
• The bile molecule is interesting in that different parts of it
have different chemical properties.
• Part of the structure likes to be in water, part likes to be in
lipid, and the other part can go either way.
• Bile is a perfect molecule for emulsifying fat, suspending fat
in water.
• Bile is the body’s detergent.
• Cholic Acid •Glycine
(hydrophobic) (hydrophilic)

•Glycocholic Acid (amphipathic)

In the next presentation, you will
see:
Lipid digestion, absorption, transport
&
Lipid metabolism