Current Topics in Chemistry - Bruice

Dr. Glaser's "Chemistry is in the News"
To Accompany Bruice, Organic Chemistry, 3/e.
Chapter 24. Lipids.

For each of the following questions, please refer to the following article:

FIRST PRODUCTS WITH OLESTRA HIT STORES
by Carol Bidwell (Los Angeles Daily News, March 10, 1998)

Editorial Comments

Olean, the brand name for olestra, an oil made of soybeans and cottonseed by Procter & Gamble has its own website! And quite a site it is! Take at look at OLEAN.

The main purpose of the website is "consumer information" and the main message is, of course, the information that Olestra is safe. "The Vote Is In (Again): Olean Is Safe For Use In Salted Snacks" one reads in the headline. Read on and learn that "olean has now received its 30-month check-up" and it is "safe". Well, that is just great! Just what we wanted to hear. But wait a second. I don't quite get it. I though the concern was that the olestra mediated systematic loss of vitamins would manifest itself after some 20 years in an increased risk of cancer and heart disease? So how can this group of experts know that Olestra is "safe" after such a short time?

Still worried about your vitamins? Come on, keep reading the Procter & Gamble's OLEAN web site. In the FAQ section, the link What about Vitamins and Carotenoids? provides more assurances that olestra will not affect our vitamin economy. Oh, and the good people at Proctor & Gamble are even adding vitamins to make up for olestra's taking vitamins out of the other food you eat. They even say that "specific amounts" amount are added to ensure you get the right dose. You wonder how they come up with these "specific" amounts?

I guess I'll stick to butter and perhaps run a bit more.

By the way, Olestra was the topic of the David Letterman's Late Show Top-10 list on 1/25/96. Here we go ...

"Slogans For The New Fat Substitute" 

  10. "Waddle over and buy some" 
   9. "Look like Siskel, eat like Ebert" 
   8. "From the chemical vat to your mouth" 
   7. "Less noisy than liposuction, safer than barfing" 
   6. "Wouldn't you like to be less of a load?" 
   5. "Certified by the Mexican Food and Drug Administration" 
   4. "Start slurpin', Tubby" 
   3. "We can't tell you exactly how we make it, but we can say
       this: ten monkeys go into a room, and only nine come out" 
   2. "It's Newt-tritious" 
   1. "Hey, Lard-ass...this fat's for you!"

Pertinent Text References
Chapter 24. Lipids.
Chapter 24. Box on "Olestra: Nonfat with Flavor".

Questions

Question 1: What is the chemical composition of a typical triglyceride "fat"? Describe the building blocks contained in a triglyceride. Can you write down the structure of a typical triglyceride?

Answer 1: Bruice, 3/e, Chapter 24.

Question 2: What is Olestra chemically? Describe the building blocks that are contained in olestra. Can you write down the actual structure of olestra?

Answer 2: Bruice, 3/e, Chapter 24, p.1038.

Question 3: What are the reasons for olestra to function as a fat substitute in foods without providing the high calorie count associated with normal fats?

Answer 3: Olestra works as a food substitute since its physical properties are comparable to fats (large hydrophobic areas). However, the chemical properties are different. Olestra is not digested at all and thus provides zero calories.

Question 4: What effect might olestra have on your body's vitamin economy?

Answer 4: The FDA concluded that olestra-fried chips deplete the body's supply of vitamins A, D, E and K and such nutrients as carotenoids, which are found in fruits and vegetables and that scientists believe help prevent cancer and heart disease.

Chemistry & Society.
Americans are getting fat. In fact, the world over, people are getting fat. The Global Challenge of Obesity and the International Obesity Task Force list many intersting facts about obesity. Are products such as olestra part of the solution or are such product exacerbating the problem?