Olestra
Nat Cooper

Chemical Concepts
Our emphasis will be on concepts of chemistry numbered 1,2,3 in this Olestra unit. But each capsule adds new considerations.

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 structure of glycerol forces us to learn a number of "conventions" that allow us to express individual molecules on the typed page.

But we must now consider the relationship between our representation of the molecule and its macroscopic properties. Our symbols are truly helpful!

We are familiar with glycerol, an oily, water soluble liquid, and with sucrose - table sugar, a white water-soluble solid.

In general, smaller molecules will be gases or liquids, larger molecules will be solids.

Liquid boiling points will increase in a like series of compounds as the molecular size increases.

If we see these symbols - letters on a page or colored spheres as representing atoms in a molecule we might begin to make judgements about macroscopic properties of substances.

Mini Outline
Glycerol and Sucrose
Mini Outline: The second major food and biomolecule group that we will briefly discuss are the carbohydrates.  Carbohydrates are compounds that contain C, H, and O in the rough ratio of (CH₂O) _n, where n > 3. They behave as if they contain either the aldehyde or ketone functional groups and multiple hydroxyl groups. Carbohydrates make up most of the organic material on earth and fill numerous roles in all types of life. They are the starch of our potatoes and sugars in our fruits that provide us with fuel and energy stores and make up about 50% of our diets. Two other sugars, ribose and deoxyribose, form part of the structural framework of the genetic information carriers, RNA and DNA. Cellulose, a polysaccharide and the most abundant organic compound of the biosphere, forms cell walls in bacteria and plants.

Cellulose

You can look at cellulose structures.

In the linked page the structures in the tutorial are one way of representing molecular configuration.  Carbons are not shown except when they are attached to the ring.  Carbon atoms are implied to be located at the angles in the ring. Hydrogens are also not shown except for attached groups.  Yet oxygens in the ring are shown to differentiate form carbon.

Cellulose is also the indigestible "fiber" in our diets. Chitin, another polysaccharide, forms the exoskeletons of insects and crustacea. Carbohydrates are also linked to many proteins and lipids, and play a key role in cell- cell recognition.

Glycerol and Sucrose: Two compounds that are key to our Olestra Chemcase are glycerol and sucrose.

Glycerol is a three carbon alcohol that has the structure:

CH₂OHCHOHCH₂OH

Glycerol

A structural representation of glycerol in which many things are implied.  First, the three carbons are connected although that fact is not obvious in the representation.  Each carbon is bonded to four groups and each oxygen to two groups.

While glycerol is technically not a carbohydrate because it lacks either the aldehyde or ketone groups, it shares an important component in that it contains multiple hydroxyl groups.

Hydroxyl groups are important because they form attachment sites for fatty acid chains. Fatty acids and glycerol combine to form the compounds we know as the common dietary triglyceride fats.

Sucrose is a disaccharide sugar that consists of the glucose and fructose monosaccharides, which are joined by an O-glycosidic bond as shown in the structure below:

Sucrose

This molecular model is yet another representation of   microscopic molecular structure.  Carbon atoms are represented by green spheres, hydrogen atoms by gray spheres and oxygen atoms by red spheres.  This image begins to show additonal complexity over printed structures by showing three-dimensional characteristics of the sucrose molecule.

An important aspect of the sucrose molecule is that is has not three but eight hydroxyl groups that can bind fatty acid chains. This structural aspect is used in the research development and subsequent production of Olestra.

We have looked only briefly at the immense world of carbohydrates, but we will see some more details as we look at the structure of Olestra and how our bodies produce energy from the different types of foods. Let’s return to the Olestra Concept map now for a look at our final discussion of carbohydrates.