Lipids

*Latin word- lipo which means fat

*Comprise 18-25% of body weight in adults
*Contain _______,_______,_______
*Don’t have a 2:1 ratio of hydrogen and oxygen
*Amount of oxygen is usually less than that in carbohydrates resulting to a fewer polar covalent bonds
*Most lipids are insoluble in polar solvents such as water
*Hydrophobic (only the smallest lipids like fatty acids can travel freely in the watery blood)
*Nonpolar solvents such as chloroform and ether readily dissolve lipids.
*Group of fats or fat-like long chain of hydrocarbons which are insoluble in water due to the large
numbers of uncharged carbon-carbon and carbon-hydrogen bonds
*Soluble in _________ solvents such as benzene, chloroform, and ether
Major Functions of Lipids
*Serve as structural components of biological membranes
*Serve as energy reserves, predominantly in the form of fats known as triacylglycerides
*Both lipids and lipid derivatives serve as vitamins and hormones
*Lipophilic bile acids aid in lipid solubilization.
*Lipids stored as adipose tissues serve as a protective cushion around organs and as an insulating
layer just below the skin.
*Lipids like waxes are protective coatings on the leaves of plants and the skin of animals.
*Lipids are compounds of esters of fatty acids (long chain of carboxylic acids- COOH)

Fatty Acid
*Has a polar head group (represented by the carboxyl group (COOH)>hydrophilic
*Has a nonpolar tail made up of a long hydrocarbon chain (R-)> hydrophobic
**Amphipathic compounds- contains a hydrophilic and a hydrophobic group

Types of Fatty Acids

A. Saturated fatty acid- contains only single bonded carbon-to-carbon chain in the nonpolar tail
*Solids at room temperature because the regular nature of their aliphatic chains allows the molecules
to be packed in close, parallel alignment.
*The longer the aliphatic chain, the _______is the melting point.

B.Unsaturated fatty acid- contains at least one double bonded carbon to carbon chain in the nonpolar
tail

*All liquids at room temperature because the cis double bonds interrupt the regular packing of the
chains
*London dispersion forces act over a shorter segment of the chain, so _____ energy is needed to
melt them.
*The more unsaturation, the _____ the melting point because each double bond introduces more
disorder into the packing of the molecule.

Omega Fatty Acids

Omega- last letter in the Greek alphabet
Omega 1- refers to the omega end (farthest carbon from the carboxyl end)
e.g.
*Omega-6 fatty acids
arachidonic acid (has the double bond at the 6th carbon from the omega
end
*Omega-3 fatty acids

**Omega number – refers to the position of the ________nearest the methyl (CH3) end of the carbon
chain
***Omega-3 fatty acid
***Omega-6 fatty acid

Why does Eskimos have low incidence of heart disease although they have cholesterol levels in their
diets?
* Omega-3 fatty acids in marine oils provide a protection against heart disease.
Saturated Fatty Acids

Structure Melting point ( ̊C )

Lauric 12:0 CH3 (CH2)10 COOH 44

acid
Myristic 14:0 CH3 (CH2)12 COOH 58
acid
Palmitic 16:0 CH3 (CH2)14 COOH 63
acid
Stearic 18:0 CH3 (CH2)16 COOH 70
acid
Arachidic 20:0 CH3 (CH2)18 COOH 77
acid

Unsaturated Fatty Acids

Structure Melting point
( ̊C )

Palmitoleic 16:1 CH3 (CH2)5 CH=CH (CH2)7 COOH 1

acid
Oleic acid 18:1 CH3 (CH2)7 CH=CH (CH2)7 COOH 16

Linoleic 18:2 CH3 (CH2)4 (CH=CHCH2)2 (CH2)6 COOH -5

acid
Linolenic 18:3 CH3 CH2 (CH=CHCH2)3 (CH2)6 COOH -11
acid
Arachidoni 20:4 CH3 (CH2)4 (CH=CHCH2)4 (CH2)2 COOH -49
c acid

Essential fatty acids

*The body cannot synthesize them from precursors and they should be included in the diet.
e.g.
1. Linoleic – omega-6 fatty acid and
2. Linolenic – omega-3 fatty acid
* Founds in plant oils, nuts, seeds, whole grains and fish

What type of fatty acid is contained more in most vegetable oils?

Coconut oil has only a small amount of unsaturated acids.
* Why is it liquid?
** It is rich in low molecular weight fatty acids chiefly lauric acid (not because it contains many double
bonds)
Glycerol
*Glycerin; glycerine; 1,2,3-propanetriol
*CH2OHCHOHCH2OH
*Colorless, odorless, sweet-tasting, syrupy liquid
*Trihydric alcohol

A. Simple Lipids
1. Triacylglycerides
-fatty acids are generally stored as neutral
lipids called TRIACYLGLYCEROLS (TAG;
Triglycerides)
*composed of three fatty acyl residues
esterified to glycerol (a three-carbon sugar
alcohol)

glycerol + 3 fatty acids  triglyceride +

3H2O

*May either be solid (fats) or liquids (oils) depending on their fatty acid composition and on the
temperature
*Triacylglycerols containing only saturated fatty acids are _____ at normal body temp., while those
that contain unsaturated fatty acids are liquids at normal body temp.
*Triesters of ______ and long-chain fatty acids

Points to remember:
1. The alcohol of triglycerides is always______.
2. The acid component of fats may be any fatty acid
w/ the ff. properties:
* Fatty acids are all unbranched fatty acids.
*They range in size from 10 to 20 carbon atoms.
*They contain even number of carbon atoms.
*Aside from the –COOH group, they have no other
functional group except the double bonds
*Fatty acids that have double bonds, the cis isomers
predominate.
Energy Yields:
*Fat  9 kcal or calories per gram of fat
*Carbohydrates ___ kcal or calories per gram
*Proteins 4 kcal or calories per gram
** Note: TAG accumulates in adipose tissues (fat cells) w/c means of storing large amount of energy.

Properties of TAG
1. Physical state
* Fats that come from animals are generally _____ at room temp.
*those from plants or ____ are usually liquids
*Liquid fats are often called ______.
Solid fats vs. liquid oils
**Structural difference (degree of unsaturation)
Which contain mainly saturated fatty acids, vegetable oils or solid animal fats?
Vegetable oils contain high amounts of unsaturated fatty acids, TRUE or FALSE?

2. Hydrogenation – addition of hydrogen to unsaturated fat

Advantages:
a. Makes it more “solid” or firm
b. Effects stability and protects against oxidation; more “shelf-stable
c. Widely used by food industry in margarine, shortening, peanut butter, baked goods & snack food

Cis vs. trans-fatty acids

*In nature, most double bonds are cis meaning that the hydrogens next to the double bonds are on
the same side of the carbon chain
*When a fat is partially hydrogenated, some of the double bonds change from cis to trans.

3. Saponification
-base-catalyzed hydrolysis of fats and oils producing glycerol and a mixture of fatty acid salts called
soaps

Rancidity
Prevention:
*Fats and oils are kept refrigerated.
*Fats and oils are kept in dark bottles.
*Antioxidants

2. Waxes
*Fatty acid + long chain alcohols

Which has higher melting point, wax or fat?...harder?

* Important waxes:
A. carnauba wax- from a Brazilian palm tree, composed of mainly myricyl cerotate, used in floor wax
and automobile wax
B. spermaceti- composed mainly of cetyl palmitate, present in whales, used as perfumes or
fragrances
C. Lanolin- from lamb’s wool, used to make cosmetics, polishes, candles and ointments