Chemistry 121 Winter 2016
Introduction to Organic Chemistry and Biochemistry
Instructor Dr. Upali Siriwardane (Ph.D. Ohio State)
E-mail: upali@latech.edu
Office: 311 Carson Taylor Hall ; Phone: 318-257-4941;
Office Hours: MTW 8:00 - 10:00 am;
ThF 9:00 - 10:00 am 1:00 - 2:00 pm.
December 18, 2015: Test 1 (Chapters 12-13)
January 25 , 2016: Test 2 (Chapters 14-16)
February 17, 2016: Test 3 (Chapters 17-19)
February 29, 2016: Test 4 (Chapters 20-22)
March 1 , 2016:
Make Up Exam: Chapters 12-22)
Bring Scantron Sheet 882-E
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Chapter 19 and GHW#9
Questions and Slides
Lipids
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Chapter 19: Lipids
19.1 Structure and Classification of Lipids, 654
19.2 Types of Fatty Acids, 656
19.3 Physical Properties of Fatty Acids, 659
19.4 Energy-Storage Lipids: Triacylglycerols, 661
19.5 Dietary Considerations and Triacylglycerols, 664
19.6 Chemical Reactions of Triacylglycerols, 669
19.7 Membrane Lipids: Phospholipids, 674
19.8 Membrane Lipids: Sphingoglycolipids, 681
19.9 Membrane Lipids: Cholesterol, 682
19.10 Cell Membranes, 684
19.11 Emulsification Lipids: Bile Acids, 687
19.12 Messenger Lipids: Steroid Hormones, 689
19.13 Messenger Lipids: Eicosanoids, 692
19.14 Protective-Coating Lipids: Biological Waxes, 694
19.15 Saponifiable and Nonsaponifiable Lipids, 697
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Lipids
A wide variety of naturally occurring organic compounds
classified together on the basis of common solubility
properties: insolubility in water
insoluble in water
Lipids include
a) Waxes: Esters of long chain fatty acids and alcohols
b) Triglycerides: Fatty acid esters of glycerol
c) Phospholipids: Fatty acid and phosphate esters of glycerol
d) Prostaglandins: structures based on Eicosanoids
e) Glycolipids: structures based on Spingosine
f) cholesterol, steroid hormones, and bile acids
g) fat-soluble vitamins
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Lipid Structures
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Eicosanoids: Messenger lipids
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Glycolipids based on spingosine
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Lipid classification by function
Energy-storage lipids – A fat, triacylglycerols or
triglycerides.
Membrane lipids - phospholipids,
sphingoglycolipids, and cholesterol
Emulsification lipids - bile acids, soaps and
detergents
Chemical messenger lipids - steroid hormones,
eicosanoids, and prostaglandins
Protective-coating lipids - biological waxes
Fat-soluble vitamins – E.g. Vitamin A
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Common Names of Carboxylic Acids
Fatty Acids: Lipid Building Blocks
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Fatty Acid Names
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Fatty Acids: Lipid Building Blocks
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Polyunsaturated fatty acids: omega-3
and omega-6 fatty acids
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Essential Fatty Acids (EFA).
Fatty acids that cannot be produced by the
body and are necessary for proper
metabolism. The OMEGA 6 and OMEGA 3
fatty acids are referred to as Essential Fatty
Acids (EFA).
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Physical Properties of Fatty Acids
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1) Give names of the following types of
lipids.
a) Name:____________
b) Name:____________
c) ) Name:____________ d) Name:____________
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1) Give names of the following types of
lipids.
e) Name:____________
f) Name:____________
g) Name:____________ h) Name:____________
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1) Give names of the following types of lipids.
i) Name:____________
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j) Name:____________
k) Name:____________
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2) Give the type, structure notation and
names of the following fatty acids.
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3) Draw the condensed structures of each of the
following fatty acids:
a. Decanoic acid
c. trans-5-Decenoic acid
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b. Stearic acid
d. cis-5-Decenoic acid
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4) Write an equation for each of the following
reactions:
a) Esterification of glycerol with three
molecules of myristic acid
b) Base (NaOH) hydrolysis or saponification of
glyceryl tristearate
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4) Write an equation for each of the following
reactions:
c) Reaction of decanoic acid with KOH
d) Hydrogenation of linoleic acid
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Phospholipids
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5) What are the structural differences between
triglycerides (triacylglycerols) and
phospholipids? Where they are found in living
organisms?
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Spingosine and Spingolipids
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6) What is a sphingolipid? Draw an example.
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Steroids
Contains a characteristic arrangement of four cycloalkane rings
that are joined to each other. Examples of steroids include the
dietary fat cholesterol:
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7) What is a steroid? What are their
applications?
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8) What are the two major types of fat
substitutes and how they work
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How aspirin relieves pain and inflammation?
Aspirin inhibits the production of prostaglandins
Concept of COX enzyme inhibition
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Acetaminophen (Tylanol)
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Triglycerides and lipoproteins:
high-density (HDL)or (LDL) lipoproteins
Lipoprotein particles: chylomicrons
Triglycerides transportation in the blood stream
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Four major groups of plasma lipoproteins.
1. Chylomicrons
2. Very low-density lipoproteins (VLDL)
3. Low-density lipoproteins (LDL)
4. High-density lipoproteins (HDL)
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Triglycerides and lipoproteins:
high-density (HDL)or (LDL) lipoproteins
Lipoprotein particles: chylomicrons
Triglycerides transportation in the blood stream
chylomicron remnant
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The roles of HDL, LDL, and cholesterol.
Cholesterol and lipoproteins are related plaque that
causes heart attacks and most strokes.
When LDL levels are low, atherosclerosis and heart
attacks are almost unknown.
High HDL levels are associated with a reduced risk of
heart disease: "good" cholesterol
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