1. Created By Prof. Gary F. Porter, Ph.D.
Lipids
Created By Prof. Gary F. Porter, Ph.D.
© 2014 by John Wiley & Sons, Inc. All rights reserved.

2. Table of Contents (hyperlinked)
Introduction
Fatty Acids and Triacylglycerols
Terpenes and Terpenoids
Steroids
Prostaglandins
Phospholipids and Cell Membranes
Waxes
© 2014 by John Wiley & Sons, Inc. All rights reserved.

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1. Introduction
Lipids
dissolve in non-polar solvents
include a variety of structural types
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Fatty Acids and Triacylglycerols
Fatty Acids
are long chain (>14 carbons) carboxylic acids,
have an even number of carbons,
are saturated (no double bonds), and
unsaturated (contain double bonds).
All double bonds are cis.
Double bonds have weakened intermolecular forces because of a molecular bend.
They have lower melting points.
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Fatty Acids and Triacylglycerols
Triacylglycerol
are 3 Fatty Acids & Glycerol, and
produce monomeric units by hydrolysis.
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Fatty Acids and Triacylglycerols
2A. Hydrogenation of Triacylglycerols
Increases M.P.
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Fatty Acids and Triacylglycerols
2B. Biological Functions of Triacylglycerols include:
long term storage of energy, and
helping us survive starvation conditions.
Fat and health
Saturated fats are linked to heart disease.
Too much fat in the diet is a health concern.
Physical properties
Fat is a solid. (saturated)
Oil is a liquid. (unsaturated)
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Fatty Acids and Triacylglycerols
2C. Saponification of Triacylglycerol
Involves the basic hydrolysis of a triacylglycerol.
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Fatty Acids and Triacylglycerols
Soap is a
monovalent anion,
dissolves dirt, and
dirt remover.
Multivalent Cations – Ca2+ Fe2+ Fe3+ Mg2+
Soap scum (precipitated soap) is caused by multivalent cations.
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Fatty Acids and Triacylglycerols
Detergent
is a multivalent anion,
keeps multivalent metals solvated, and
prevents soap scum.
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Fatty Acids and Triacylglycerols
2F. Reactions of the Carboxyl Group of Fatty Acids
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Fatty Acids and Triacylglycerols
2E. Reactions of the Alkenyl Chain Group of Unsaturated Fatty Acids
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Terpenes and Terpenoids
The monomeric unit is
isoprene, and
5 carbons.
Polymeric Molecules
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Terpenes and Terpenoids
See how to find the terpene monomers in the polymers below.
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Terpenes and Terpenoids
Practice Problem 23.2
Show the isoprene units in each of the following terpenes.
Classify each as a monoterpene, diterpene, sesquiterpene, and so on.
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Terpenes and Terpenoids
Carotenes
contain two tetraterpenes
Vitamin A
is a precursor of a
carotene, and
- is a tetraterpene.
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Terpenes and Terpenoids
3A. Natural Rubber Vulcanization creates disulfide linkages between chains.
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18. Prepared by Dr. Khalid Shadid
Steroids
4A. Structure and Systematic Nomenclature
Cyclopentophenanthrenes
α substitution – Group is trans to C-18 methyl
β substitution – Group is cis to C-18 methyl
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19. 4A. Structure and Systematic Nomenclature
Steroids
4A. Structure and Systematic Nomenclature
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Steroids
4B. Cholesterol
Dietary Cholesterol
is a mixture of lipids, one of which is cholesterol.
HDL – High Density Lipoproteins
travel from tissues to liver, and
are an indicator of good health.
LDL – Low Density Lipoproteins
travel from liver to tissues, and
are an indicator of poor health.
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Steroids
4C. Sex Hormones
Estrogens – female hormone
Androgens – male hormone
Progestins – pregnancy hormone
Suppress ovulation.
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Steroids
The Enzyme Aromatase and its Chemistry
converts a male hormone into a female hormone.
The Chemistry:
Estrogen in brain effects male behavior.
Testosterone is converted to estrogen by aromatase in the brain.
An aromatase deficiency causes a deficit in male sexual behavior (in the brain).
After menopause, aromatase produces estrogen for women.
Aromatase inhibitors block estrogen synthesis to control estrogen activated breast cancer.
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Steroids
4D. Adrenocortical Hormones
are 28 different Hormones,
are produced in the adrenal cortex located in adrenal glands found on top of the kidneys, and
drive numerous biological regulation activities including the inflammatory response.
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Steroids
4E. D Vitamins
Sunlight is needed to produce Vitamin D3. VitaminD3 is needed for health and facilitates the process by which calcium is absorbed to allow proper bone growth.
© 2014 by John Wiley & Sons, Inc. All rights reserved.

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Steroids 1. 2. 3. 4.
4F. Other Steroids
are isolated from digitalis and strengthen heart muscle,
are isolated from bile and emulsify lipids by acting as a soap and aiding in the digestive process,
are isolated from soybean oil and inhibit dietary cholesterol absorption, and
are isolated from plant sources and are used to synthesize cortisone and sex hormones.
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Steroids
4G. Reactions of Steroids (Cholesterol)
involves the double bond
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Steroids
4G. Reactions of Steroids (Cholestane)
Reactivity of equatorial vs. axial hydroxyls
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5. Prostaglandins
Structure
Includes twenty carbons and a
Five membered ring.
Synthesized from
Arachidonic Acid
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6. Phospholipids and Cell Membranes
Three Components are
Glycerol,
2 Fatty Acids, and
Phosphate.
Phosphatide
Has another group, typically bonds to phosphate.
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6. Phospholipids and Cell Membranes
6A. Phosphatide Has four important classes as shown on the right.
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6. Phospholipids and Cell Membranes
6A. Phosphatide - Is a soap-like molecule.
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6. Phospholipids and Cell Membranes
6A. Phosphatide
Is found in cell walls
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6. Phospholipids and Cell Membranes
6B. Derivatives of Sphingosine (Parent Molecule)
Sphingomyelin
is a component of myelin found in nerve cell membranes (sheaths).
Cerebroside
is a brain cell membrane component.
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Waxes
-Most waxes are esters of long-chain fatty acids and long-chain alcohols.
-Act as a water resistant coat
-Waxes are found as protective coatings on the skin, fur, and feathers of animals and on the leaves and fruits of plants.
-Several esters isolated from waxes are the following:
© 2014 by John Wiley & Sons, Inc. All rights reserved.