13-Hydroxyoctadecadienoic acid

13-Hydroxyoctadecadienoic acid

Chemical structure of 13-Hydroxyoctadecadienoic acid

13-Hydroxyoctadecadienoic acid, commonly abbreviated as 13-HODE, is a type of hydroxy fatty acid derived from the oxidation of linoleic acid. It is one of the primary products formed during the enzymatic and non-enzymatic oxidation of linoleic acid, a common polyunsaturated fatty acid found in many vegetable oils.

Formation

13-HODE is formed through the action of lipoxygenase enzymes, which catalyze the oxidation of linoleic acid. This process involves the insertion of molecular oxygen into the fatty acid chain, resulting in the formation of a hydroperoxide intermediate. The hydroperoxide is then reduced to form 13-HODE. Non-enzymatic pathways, such as free radical oxidation, can also produce 13-HODE.

Biological Functions

13-HODE plays a role in various biological processes. It is involved in the regulation of inflammation and has been shown to have anti-inflammatory properties. Additionally, 13-HODE can influence cell signaling pathways and modulate the activity of nuclear receptors such as PPAR gamma.

Clinical Significance

The levels of 13-HODE in the body can be indicative of oxidative stress and inflammation. Elevated levels of 13-HODE have been associated with various pathological conditions, including atherosclerosis, diabetes, and certain types of cancer. As a result, 13-HODE is often studied as a potential biomarker for these diseases.

Related Compounds

13-HODE is part of a larger family of oxidized fatty acids known as oxylipins. Other related compounds include 9-Hydroxyoctadecadienoic acid (9-HODE) and various prostaglandins and leukotrienes. These compounds collectively play important roles in the regulation of inflammation and immune responses.

Related Pages

• Linoleic acid
• Lipoxygenase
• Oxidative stress
• Atherosclerosis
• PPAR gamma