Lipids: Understanding the Properties and Composition of Fatty Acids and Lipids | Summaries Biochemistry

Experiment 12 –Lipids

Lipids are a class of biological molecules that are insoluble in water and soluble

in nonpolar solvents. There are many different categories of lipids and each category has

different components present in its structure.

Fatty acids are components of many types of lipids. Fatty acids are carboxylic

acids with very long hydrocarbon chains, usually 12-18 carbon atoms long. Even though

these carboxylic acids can hydrogen bond with water, they are insoluble because of the

length of their hydrocarbon chains. Fatty acids can be saturated or unsaturated. A

saturated fatty acid contains no carbon-carbon double bonds, so it is “saturated” with

hydrogen. Unsaturated fatty acids contain one or more cis double bonds. (Very few

naturally occurring fatty acids contain trans double bonds.) The presence of cis double

bonds has an important effect on the melting point of the fatty acid. Cis double bonds

form rigid kinks in the fatty acid chains (remember that there is no rotation around a

double bond), and the result is that unsaturated fatty acids can not line up very well to

give a regularly arranged crystal structure. Saturated fatty acids, on the other hand, line

up in a very regular manner. The result of this is that saturated fatty acids have high

melting points and are usually solids at room temperature. Unsaturated fatty acids,

however, have low melting points and are usually liquids at room temperature. The

names, structures, and melting points of some common fatty acids are shown in the table

below.

Structures of Common Fatty Acids

Name

Number

of carbons

Structure

Melting

Point (°C)

Saturated Fatty Acids

Lauric acid

CH3(CH2)10COOH

Myristic acid

CH3(CH2)12COOH

Palmitic acid

CH3(CH2)14COOH

Stearic acid

CH3(CH2)16COOH

Unsaturated Fatty Acids (all double bonds are cis)

Palmitoleic

acid

CH3(CH2)5CH=CH(CH2)7COOH

-1

Oleic acid

CH3(CH2)7CH=CH(CH2)7COOH

Linoleic acid

CH3(CH2)4CH=CHCH2CH=CH(CH2)7COOH

-5

Linolenic

acid

CH3CH2CH=CHCH2CH=CHCH2CH=CH(CH2)7COOH

-11

Waxes are lipids that are used in nature as protective coatings. Structurally, a wax

molecule is an ester of a long-chain alcohol and a long-chain fatty acid. Naturally

occurring waxes are mixtures of different molecules. There are natural waxes present on

the surfaces of many fruits and leaves, in beeswax, and on the feathers of aquatic birds.

Fats and oils both belong to a class of molecules called triacylglycerols or

triglycerides. Fats usually come from animal sources and are solids at room temperature,

and oils are generally from plant sources and are liquids at room temperature.

Triglycerides are triesters of glycerol and three fatty acid molecules. The fatty acids in

the triglyceride can be the same or different. Naturally occurring fats and oils are

typically mixtures of different triglycerides. The melting point of a particular fat or oil

depends on the proportions of saturated and unsaturated fatty acid components present.

For example, butter (which is a fat) contains about 30% unsaturated fatty acids and about

70% saturated fatty acids and cholesterol. Corn oil contains about 88% unsaturated fatty

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Experiment 12 – Lipids

Lipids are a class of biological molecules that are insoluble in water and soluble in nonpolar solvents. There are many different categories of lipids and each category has different components present in its structure. Fatty acids are components of many types of lipids. Fatty acids are carboxylic acids with very long hydrocarbon chains, usually 12-18 carbon atoms long. Even though these carboxylic acids can hydrogen bond with water, they are insoluble because of the length of their hydrocarbon chains. Fatty acids can be saturated or unsaturated. A saturated fatty acid contains no carbon-carbon double bonds, so it is “saturated” with hydrogen. Unsaturated fatty acids contain one or more cis double bonds. (Very few naturally occurring fatty acids contain trans double bonds.) The presence of cis double bonds has an important effect on the melting point of the fatty acid. Cis double bonds form rigid kinks in the fatty acid chains (remember that there is no rotation around a double bond), and the result is that unsaturated fatty acids can not line up very well to give a regularly arranged crystal structure. Saturated fatty acids, on the other hand, line up in a very regular manner. The result of this is that saturated fatty acids have high melting points and are usually solids at room temperature. Unsaturated fatty acids, however, have low melting points and are usually liquids at room temperature. The names, structures, and melting points of some common fatty acids are shown in the table below.

Structures of Common Fatty Acids

Name Number of carbons Structure Melting Point (°C) Saturated Fatty Acids Lauric acid 12 CH 3 (CH 2 ) 10 COOH^44 Myristic acid 14 CH 3 (CH 2 ) 12 COOH^58 Palmitic acid 16 CH 3 (CH 2 ) 14 COOH^63 Stearic acid 18 CH 3 (CH 2 ) 16 COOH^70 Unsaturated Fatty Acids (all double bonds are cis ) Palmitoleic acid

16 CH 3 (CH 2 ) 5 CH=CH(CH 2 ) 7 COOH^ - 1

Oleic acid 18 CH 3 (CH 2 ) 7 CH=CH(CH 2 ) 7 COOH^4 Linoleic acid 18 CH 3 (CH 2 ) 4 CH=CHCH 2 CH=CH(CH 2 ) 7 COOH^ - 5 Linolenic acid

18 CH 3 CH 2 CH=CHCH 2 CH=CHCH 2 CH=CH(CH 2 ) 7 COOH^ - 11

Waxes are lipids that are used in nature as protective coatings. Structurally, a wax molecule is an ester of a long-chain alcohol and a long-chain fatty acid. Naturally occurring waxes are mixtures of different molecules. There are natural waxes present on the surfaces of many fruits and leaves, in beeswax, and on the feathers of aquatic birds. Fats and oils both belong to a class of molecules called triacylglycerols or triglycerides. Fats usually come from animal sources and are solids at room temperature, and oils are generally from plant sources and are liquids at room temperature. Triglycerides are triesters of glycerol and three fatty acid molecules. The fatty acids in the triglyceride can be the same or different. Naturally occurring fats and oils are typically mixtures of different triglycerides. The melting point of a particular fat or oil depends on the proportions of saturated and unsaturated fatty acid components present. For example, butter (which is a fat) contains about 30% unsaturated fatty acids and about 70% saturated fatty acids and cholesterol. Corn oil contains about 88% unsaturated fatty

acids and about 12% saturated fatty acids. In general, the higher the degree of unsaturation, the lower the melting point of the fat or oil. Shown below is the reaction of a molecule of glycerol with three molecules of stearic acid to form a triglyceride molecule and three molecules of water. Cholesterol is a steroid and has a very different structure from other types of lipids. The structure of cholesterol is shown on the next page. It is classified as a lipid because it is nonpolar and therefore insoluble in water. Phospholipids contain a charged phosphate and a charged amino alcohol in addition to having long nonpolar chains. Therefore, they have a dual nature – one end of the molecule is charged and therefore compatible with water, and the other end is nonpolar and therefore compatible with nonpolar substances. Phospholipids are the main components of cell membranes, where they are arranged in a lipid bilayer. The charged ends face the solvent (water), and the nonpolar ends face each other in the interior of the membrane. Phospholipids can be further classified as glycerophospholipids or sphingolipids. Glycerophospholipids contain glycerol, 2 fatty acids, a phosphate group, and an amino alcohol. Phosphate-containing sphingolipids contain sphingosine, one fatty acid, a phosphate group, and an amino alcohol. H 2 C CH OH OH

C O 3 HO^ (CH 2 ) 16 CH 3 H 2 C CH O C (CH 2 ) 16 CH 3 O C (CH 2 ) 16 CH 3 O O C H 2 O C O (CH 2 ) 16 CH 3
3 H 2 O C H 2 OH Glycerol (^) Stearic Acid Glyceryl tristearin HO CH 3 Cholesterol

Using the model of glyceryl triacetate, hydrolyze the ester bonds by adding one molecule of water to each. Write the equation for this reaction. This hydrolysis reaction is usually catalyzed by acid or an enzyme. Part 2 - Physical Properties of Lipids and Fatty Acids
Label 7 clean, dry test tubes. Put a small sample of each of the following lipids in separate test tubes: olive oil, safflower oil, stearic acid, oleic acid, lecithin, cholesterol and vitamin A. If the lipid is a solid, use a very small amount on the tip of a spatula. If the lipid is a liquid, use 5 drops. If the vitamin A is given as a capsule, you will need to puncture it and squeeze out some of the liquid inside to test it.
Classify each of the lipids as a triglyceride, fatty acid, steroid, or phospholipid.
Describe the appearance and odor, if any, of each of the lipids.
Add 20 drops of methylene chloride to each tube and shake each of the tubes to mix the solutions well. Determine whether each of the lipids is soluble or insoluble in methylene chloride. Record your observations on the report sheet. Save these solutions for part 3!
Label 7 clean test tubes. (The tubes do not have to be dry this time.) Put a small sample of each of the lipids in separate test tubes, as you did in step 4.
Add about 2 mL of deionized water to each test tube and shake each tube to mix thoroughly. Determine whether each of the lipids is soluble or insoluble in water. Record your observations on the report sheet. Part 3 - Bromine Test
For this part, you will need the samples from step 7. To each solution, add 1% bromine solution drop by drop, shaking the tube after each drop, until the solution remains orange. If you add 1 drop of bromine and the orange color of the bromine does not disappear, do not add any more bromine. If your sample contains no double bonds, it will not react with bromine and the orange color of bromine will not disappear, even if only one drop of bromine is added. If your sample contains double bonds, it will react with the added bromine, and the orange color will disappear. The more double bonds present in the sample, the more bromine will be needed to react with the sample. The orange color of bromine remains in the solution when all of the double bonds have reacted.
Record your observations – you will need to notice whether the orange color fades rapidly or persists in each case.

Questions

What functional group is present in a triglyceride?
What functional group is present in a fatty acid?
Draw the structure of oleic acid.
Draw the structure of glyceryl triolein.
What do lipids have in common?
What type of solvent would be needed to remove an oil spot? Why?
The melting point of stearic acid is 70°C, and the melting point of oleic acid is 4°C. Explain in detail why their melting points are so different.
Based on part 3 of the experiment, which oil is more unsaturated, safflower oil or olive oil? Explain.
Which should have a higher melting point, safflower oil or olive oil? Explain your reasoning.
What components are present in a phosphoglyceride?

Why is it that phosphoglycerides are found in cell membranes?

Lipids: Understanding the Properties and Composition of Fatty Acids and Lipids, Summaries of Biochemistry

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Experiment 12 – Lipids

Structures of Common Fatty Acids

16 CH 3 (CH 2 ) 5 CH=CH(CH 2 ) 7 COOH^ - 1

18 CH 3 CH 2 CH=CHCH 2 CH=CHCH 2 CH=CH(CH 2 ) 7 COOH^ - 11

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