The Chemistry of Biology: Lipids

Lipids
The Chemistry of Biology

 Introduction

 Atomic Theory

 Chemical Reactions: Ionic, Covalent, and Polar Covalent Bonds

 Water

 Organic Chemistry

 Carbohydrates

 Lipids

 Proteins

 Nucleic Acids

 Vitamins and Minerals

Lipids are organic compounds that contain the same elements as carbohydrates: carbon, hydrogen, and
oxygen. However, the hydrogen-to-oxygen ratio is always greater than 2:1. More important for biological
systems, the carbon-to-hydrogen bonds are nonpolar covalent, which means that lipids are fat soluble
and will not dissolve in water. There are four biologically important lipids:

 Fats

 Waxes

 Phospholipids

 Steroids

Fats
Fats are large molecules that are composed of three fatty acid molecules bonded to a glycerol molecule.
The fatty acid molecule is a long chain of covalently bonded carbon atoms with nonpolar bonds to
hydrogen atoms all along the carbon chain with a carboxyl group attached to one end. Because the
carbon-hydrogen bonds are nonpolar, the chain is hydrophobic, meaning they are not water soluble.
Glycerol is a three-carbon-chain compound that bonds with the fatty acids to create a fat. Typically, each
carbon in the glycerol molecule bonds via dehydration synthesis to the first carbon atom from a fatty acid
molecule so that the resulting fat molecule appears to have a glycerol head with three fatty acid chains
streaming from it. This resulting molecule is called a triglyceride. Because carbon-hydrogen bonds are
considered energy rich, fats store a lot of energy per unit. In fact, a gram of fat stores more than twice as
much energy as a gram of a polysaccharide such as starch. Fats are lipids that are used by living
organisms for stored energy.
A saturated fatty acid has hydrogen atoms bonded to all available carbon atoms. An unsaturated fatty acid
has one or more carbon atoms double-bonded to the neighboring carbon atom so that fewer hydrogen
atoms are needed to create a stable electron cloud. With fewer hydrogen atoms attached, the molecule is
considered unsaturated with hydrogen atoms. So saturated fatty acids have more hydrogen atoms
attached than unsaturated fatty acid chains. Through their metabolism, plants generally produce
triglycerides that contain unsaturated fatty acids such as peanut oil or olive oil, whereas animals generally
produce triglycerides that contain saturated fatty acids which humans sometimes convert into butter and
lard.

Waxes
Waxes are similar to fats except that waxes are composed of only one long-chain fatty acid bonded to a
long-chain alcohol group attached. Because of their long, nonpolar carbon chains, waxes are extremely
hydrophobic (meaning they lack an affinity for water). Both plants and animals use this waterproofing
characteristic as part of their composition. Plants most noticeably use waxes for a thin protective covering
of stems and leaves to prevent water loss. Similarly, animals employ waxes for protective purposes; for
instance, earwax in humans prevents foreign material from entering and possibly injuring the ear canal
area.

Phospholipids
Phospholipids are similar to fats except they have two fatty acid chains bonded to a glycerol plus they
contain the element phosphorus. Phospholipids are unique because they have a hydrophobic and
a hydrophilic (water-soluble) end. Phospholipids are biologically important because they are the main
structural components of cell membranes. The cell membrane is called a phospholipid bilayer because it
consists of two phospholipid layers oriented so that the hydrophyllic “head” of both molecules face the
exterior and the hydrophobic “tails” of both molecules create the interior of the membrane. Therefore,
water and other cellular fluids are contained. The hydrophobic ends for both molecules face each other on
the inside and allow for passage of acceptable, and some objectionable, materials through the cell
membrane.

Steroids
Steroids are structurally different from the other lipids. The carbon skeleton of steroids is bent to form four
fused rings that do not contain fatty acids. The most common steroid, cholesterol, is needed to make both
the male (testosterone) and female (estrogen) sex hormones, and it is a component of cell membranes
and is needed for the proper function of nerve cells. Excessive amounts of cholesterol, however, have
been linked to heart disease. Another popular steroid group is the anabolic steroids that are man-made
and mimic the effect of the male hormone, testosterone. Originally intended as a treatment for anemia
and certain diseases that destroy muscle, athletes have recently been using them to increase muscle
mass, stamina, and strength—which they will do. However, the performance-enhancement drugs come
with a price. The anabolic steroids are linked to increased cholesterol levels, mood swings, reduced sex
drive, possible infertility, and possible connections between liver damage and the resulting liver cancer.
Certain beneficial fat-soluble hormones, such as cortisol, are also familiar steroids.
Excerpted from The Complete Idiot's Guide to Biology © 2004 by Glen E. Moulton, Ed.D.. All rights reserved including the
right of reproduction in whole or in part in any form. Used by arrangement with Alpha Books, a member of Penguin Group
(USA) Inc.

To order this book direct from the publisher, visit the Penguin USA website or call 1-800-253-6476. You can also purchase
this book at Amazon.com and Barnes & Noble.

See also:

 The Chemistry of Biology: Organic Chemistry

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There is only one characteristic that is common to all lipids, and that is
their inability to dissolve in water. They will, however, dissolve in a
variety of organic solvents, such as benzene, acetone, alcohol, carbon
tetrachloride,and chloroform. This single commonality is generally used
to classify something as a lipid.

Beyond that one charcteristic, lipids display a wide variety of structures

and features. They include oils, fats, and waxes; they can be liquid or
solid at room temperature, and they may have other functional groups of
various kinds attached. One example of this would be the phospholipids
that comprise the majority of the cell membrane. In these membranes, it
is the fact that lipids are chemically incompatible with water that actually
helps to create the structure of the membrane.
3

The terms "saturated" and "saturation" may have different meanings in

chemistry, depending on the context in which they are used. Here are the three
most common definitions:

Saturated Definition #1
This chemistry definition refers to a saturated compound. A saturated substance
is one in which the atoms are linked by single bonds. A fully
saturated compound contains no double or triple bonds. Alternatively, if a
molecule contains double or triple bonds, it is considered to be unsaturated.

Example: ethane (C2H6) is a saturated hydrocarbon that has no double or triple

bonds, while ethylene has a C=C double bond and ethyne has a carbon-carbon
triple bond. An organometallic complex is said to be unsaturated if it has fewer
than 18 valence electrons and is therefore exposed to oxidative coordinate or
addition of another ligand.

Saturated Definition #2
This definition refers to a saturated solution. In this context, saturated refers to a
point of maximum concentration, in which no more solute may be dissolved in
a solvent. Saturation, in this context, depends on temperature and pressure.
Usually, raising the temperature allows a solution to dissolve more solute.

Example: When you grow crystals from an aqueous (water) solution, you
dissolve as much solute into the water as you can, to the point where no more will
dissolve. This produces a saturated solution.

Saturated Definition #3
 Although not a technical chemistry definition, saturated may mean thoroughly
soaked with as much water or other solvent as possible.

Example: If a protocol asks you to completely saturate a filter paper with

solution, this means to thoroughly wet it. If an atmosphere is at its highest
humidity level for a given temperature, it is saturated with water vapor.

Most animal fats are saturated. The fats of plants and fish are generally
unsaturated. ... Examples of foods containing a high proportion of saturated fat include
animal fat products such as cream, cheese, butter, other whole milk dairy products and
fatty meats which also contain dietary cholesterol.
CITE
Monounsaturated fatty acid (monounsaturated fat): A fatty acid having one carbon-
carbon double bond in its carbon chain. Stearic acid lacks a carbon-carbon double bond
in its carbon chain, so this molecule is a saturated fatty acid.

polyunsaturated
adjective
poly∙un∙sat∙u∙rat∙ed | \ ˌpäl-ē-ˌən-ˈsach-ə-ˌrāt-əd \

Medical Definition of polyunsaturated

of an oil, fat, or fatty acid
: having in each molecule many chemical bonds in which two
or three pairs of electrons are shared by two atom
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Polyunsaturated fatty acid

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Polyunsaturated fatty acids (PUFAs) are fatty acids that contain more
than one double bond in their backbone. This class includes many important
compounds, such as essential fatty acids and those that give drying oils their
characteristic property.
Polyunsaturated fatty acids can be classified in various groups by their
chemical structure:

 methylene-interrupted polyenes
 conjugated fatty acids
 other PUFAs

Based on the length of their carbon backbone, they are sometimes classified
in two groups:[1]
 short chain polyunsaturated fatty acids (SC-PUFA), with 16 or 18
carbon atoms
 long-chain polyunsaturated fatty acids (LC-PUFA) with more than 18
carbon atoms

Polyunsaturated fat is a type of dietary fat. It is one of the healthy fats, along with
monounsaturated fat. Polyunsaturated fat is found in plant and animal foods, such as salmon,
vegetable oils, and some nuts and seeds.

Monounsaturated fatty acid (monounsaturated fat): A fatty acid having one carbon-carbon
double bond in its carbon chain. Stearic acid lacks a carbon-carbon double bond in its carbon
chain, so this molecule is a saturated fatty acid

Examples of unsaturated fatty acids are palmitoleic acid, oleic acid, myristoleic acid,
linoleic acid, and arachidonic acid. Foods containing unsaturated fats include avocado, nuts,
olive oils, and vegetable oils such as canola. Meat products contain
both saturated and unsaturated fats.