Olestra
Nat Cooper

Chemical Concepts
Fats play a significant and unique role in bodily function.

We will see how researchers used these simple chemical concepts to invent and develop olestra and we will use these principles ourselves to evaluate and decide on nutritional issues

Micro/Macro
and Symbolic
Representation

This page shows us "ball and stick" representations of three biologically important molecules of increasing complexity.

The balls represent the positions of atoms in the molecule as they realate to neighboring atoms. In the d-glucose representations we can see how carbons are linked to oxygens. We also see the shape of ONE molecule as it exists in ONE configuration.

In fact, the bonds between atoms, represented by the sticks, bend, rotate and vibrate depending on the energy of the molecule.

So the microscopic representation of molecules by the ball and stick models gives us a concept of what a single molecule might look like. But this useful model fails in that the bonds between the atoms in the billions and billions of molecules in a macroscopic sample will bend, rotate and vibrate individually so that a macroscopic sample contains molecules with an inconceivably large number of individual shapes. And these shapes change continuously.

The two equations shown on this page also represent bending, vibration and rotation and collision! In a chemical reaction, the activation energy often generated by the collisions is sufficient to provide so much energy that bonds BREAK. This is the mark of chemical reactions. Bonds in molecules are ruptured and new bonds form.

Another aspect of food molecules that is important to our Olestra Chemcase is the way that energy is produced when we burn (oxidize) a carbohydrate, protein, or a lipid.

The basic equation that describes energy production from the simplest hydrocarbon, methane, is to combine this hydrocarbon with molecular oxygen and to produce carbon dioxide and water as follows:

CH₄ + 2O₂ ->  CO₂ + 2H₂O deltaH= - 890 kJ

This means that if you burned  every mole of methane that you ate or breathed (yuck!), it would produce 890 kJ, almost 50 kJ/gram of energy. And that is about the maximum amount of energy we can expect from combustion of any molecule.

Almost 50% of the food we eat is in the more pleasant form of  starches and sugars, carbohydrate molecules. While some of these carbohydrates are the indigestible "fiber" in the form of cellulose, most are broken down to form glucose, the sugar that carries energy through our bloodstream to our cells. This combustion of glucose:

C₆H₁₂O₆ + 6O₂ -> 6CO₂ + 6H₂O

produces 16 kJ of energy or heat per gram of glucose.

d-glucose
This is a ball and stick representation of glucose C₆H₁₂O₆.   Spheres are atoms, cylinders are bonds.  The model has the advantage of showing the molecule in three dimensions.  Carbons are green, oxygens are red, hydrogens are silver.

When we eat proteins, these large molecules are often broken down into their amino acids and then reassembled to form other proteins.

Protein Model - Insulin
Ball and stick model of a representative protein, insulin.  AS with glucose (above) atoms are represented by color-coded spheres, nitrogen is blue, sulfur is yellow and bonds are represented by cylinders.
On thing we can see by inspection is that proteins are complex molecules containing significant oxygen and nitrogen.

Some of the proteins, however, are oxidized producing about 17 kJ/gram of protein of energy, close to the value for carbohydrates.

The third major energy source, fats, are composed of long hydrocarbon chains, similar to the many fuels we use in our lives such as gasoline, heating fuels, or candle waxes.

This amount of energy is close to that produced when we burn the major component of gasoline, octane, which produces 48 kJ/gram. Octane, C₈H₁₈, is a straight chained or saturated hydrocarbon with no additional oxygen as opposed to the carbohydrates.

This greater energy content of fats and saturated hydrocarbon fuels is due to the fact that these substances initially contain very little oxygen and can therefore combine with greater amounts of oxygen while they produce energy. Fortunately, though it may not always seem so, our bodies choose fats to store our energy reserves. If our bodies used glycogen instead of fats for energy storage, a typical 155 pound male would have to weigh an additional 120 pounds to carry all of the necessary energy stores as glycogen!

These differences in the way that food molecules are oxidized lead to the different food energy contents where carbohydrates and proteins yield 4 kcalories per gram while fats yield 9 kcalories per gram. This also leads to the fact that our bodies, being the wonderfully efficient organisms that they are, store any long term energy as little (or not so little) globules of fat. At this point let’s return to the Olestra Concept map and take a closer look at fat or lipid metabolism and how olestra was designed to