Palmitoleic Acid

Scientists have discovered that trans-palmitoleic acid or trans-9-hexadecenoic acid, a fatty acid found in milk, cheese, yoghurt and butter, can reduce the risk of type 2 diabetes. Trans-palmitoleic acid is not produced in the body whereas cis-palmitoleic acid is produced in the body and is already known from animal experiments to protect against diabetes.

Cis-palmitoleic acid is made in the body using palmitic acid and the enzyme delta-9 desaturase.

In 2001, scientists suggested that fatty acids, such as palmitoleic acid found on the surface of skin, decompose to form 2-nonenal which has an unpleasant smell, a bit like old books, and could be the cause of what is commonly referred to as "old person smell".

Palmitoleic acid is used by the key enzymes in the body that control fat oxidation at very high rates. It has been suggested that palmitoleic acid could therefore be used to combat obesity.

Reference
Dariush Mozaffarian, Haiming Cao, Irena B. King, Rozenn N. Lemaitre, Xiaoling Song, David S. Siscovick, and Gökhan S. Hotamisligil. Trans-Palmitoleic Acid, Metabolic Risk Factors, and New-Onset Diabetes in U.S. Adults. Annals of Internal Medicine, December 21, 2010

Further Reading
Lipids
Carboxylic Acids
Functional Groups
Enzymes

Study Questions

1. Write the molecular formula for palmitoleic acid
2. On the structural formula for palmitoleic acid shown above, locate and name two different functional groups.
3. Draw a structural formula for palmitic acid, CH₃(CH₂)₁₄COOH.
4. Locate and name the functional group present in palmitic acid.
5. Draw a structural formula for oleic acid, CH₃(CH₂)₇CH=CH(CH₂)₇COOH.
6. Locate and name the functional groups present in oleic acid.
7. In what ways is palmitoleic acid similar to palmitic acid and oleic acid?
8. In what ways is palmitoleic acid different to palmitic acid and oleic acid?
9. Draw a structural formula for 2-nonenal.
10. Write the molecular formula for 2-nonenal.
11. Locate and name the functional groups present in 2-nonenal.
12. How would cis-palmitoleic acid differ structurally from trans-palmitoleic acid?