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Radical Autoxidation

Radical Autoxidation

The oxidation of an organic compound in the presence of air or oxygen is called autoxidation. For example, cumene reacts with oxygen to form hydroperoxide. Autoxidation involves initiation, propagation, and termination steps. Many organic compounds are susceptible to autoxidation—especially ethers in the presence of oxygen, which form hydroperoxides. Even though this reaction is slow, old ether bottles contain small amounts of peroxide, which leads to laboratory explosions during ether...

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Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.

Structure of Lipids

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Lipids include a diverse group of compounds that are largely nonpolar in nature. This is because they are hydrocarbons that include mostly nonpolar carbon-carbon or carbon-hydrogen bonds. Non-polar molecules are hydrophobic (“water fearing”), or insoluble in water. Lipids perform many different functions in a cell. Cells store energy for long-term use in the form of fats. Lipids also provide insulation from the environment for plants and animals. For example, they help keep aquatic...

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Oxidation of aldehydes and ketones results in the formation of carboxylic acids. Aldehydes, bearing hydrogen next to the carbonyl group, are easily oxidized compared to ketones. This is because an aldehydic proton can easily be abstracted during oxidation.
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Related Experiment Video

Updated: Dec 4, 2025

NMR Spectroscopy as a Robust Tool for the Rapid Evaluation of the Lipid Profile of Fish Oil Supplements

Published on: May 1, 2017

Chemical Compositional Changes in Over-Oxidized Fish Oils.

Austin S Phung¹, Gerard Bannenberg², Claire Vigor³

¹Department of Chemistry, University of California, Davis, CA 95616, USA.

Foods (Basel, Switzerland)

|October 23, 2020

Summary

This summary is machine-generated.

Highly rancid fish oil, rich in omega-3 fatty acids, can cause newborn mortality. This study details chemical changes in damaged oils, identifying unique compounds formed during oxidation.

Keywords:

dietary supplement docosahexaenoic acid eicosapentaenoic acid fatty acids fish oils food analysis isoprostanoids omega-3 oxidation condition oxysterols volatiles

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Last Updated: Dec 4, 2025

NMR Spectroscopy as a Robust Tool for the Rapid Evaluation of the Lipid Profile of Fish Oil Supplements

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Determination of Total Lipid and Lipid Classes in Marine Samples

Determination of Total Lipid and Lipid Classes in Marine Samples

Published on: December 11, 2021

Area of Science:

Nutritional Biochemistry
Oxidative Chemistry
Marine Oil Analysis

Background:

Previous research linked rancid hoki liver oil to newborn rat mortality, attributing it to lipid hydroperoxides.
Other chemical alterations in damaged omega-3 oils were not fully explored.

Purpose of the Study:

To replicate oxidation conditions causing fish oil rancidity and analyze temporal chemical changes.
To investigate oxidation signatures in hoki and anchovy oils under different oxidative stresses.
To identify unique oxidation byproducts like isoprostanoids and oxysterols.

Main Methods:

Replication of oxidative damage to hoki liver oil (oxygen, light, 30 days).
Analysis of oxidative quality indices (peroxide value, p-anisidine value, etc.), fatty acids, volatiles, isoprostanoids, and oxysterols.
Comparison with refined anchovy oil and oil oxidized via thermal exposure.

Main Results:

Confirmed extreme rancidity and detailed temporal chemical changes in oxidized fish oils.
Identified distinct oxidation signatures based on oil type, antioxidant content, and oxidation method.
Discovered unique isoprostanoids and oxysterols formed in over-oxidized fish oils.

Conclusions:

Oxidation of omega-3 rich fish oils generates complex chemical changes beyond simple lipid hydroperoxides.
Antioxidant content and oxidation conditions significantly influence the resulting chemical profile of damaged fish oils.
The identified unique compounds warrant further investigation for potential biological activities.