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Related Concept Videos

Radical Formation: Elimination00:51

Radical Formation: Elimination

2.1K
Another method of radical formation is the elimination process. It is the opposite of the addition route and is driven by the instability of the radical. For example, as depicted in Figure 1, dibenzoyl peroxide yields a pair of unstable radicals upon homolysis. Given its instability, this radical spontaneously undergoes elimination via a C–C bond cleavage to form a relatively more stable phenyl radical. The mechanism involves cleavage of the bond between the α and β positions with respect...
2.1K
Radical Autoxidation01:20

Radical Autoxidation

2.9K
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...
2.9K
Radical Formation: Addition00:47

Radical Formation: Addition

2.1K
Radicals can be formed by adding a radical to a spin-paired molecule. This is typically observed with unsaturated species, where the addition of a radical across the π bond leads to the production of a new radical by dissolving the π bond. For example, the addition of a Br radical to an alkene yields a carbon-centered radical.
Similar to charge conservation in chemical reactions, spin conservation is implicit for radical reactions. Accordingly, the product formed must possess an...
2.1K
Radical Formation: Overview01:03

Radical Formation: Overview

2.5K
A bond can be broken either by heterolytic bond cleavage to form ions or homolytic bond cleavage to yield radicals. A fishhook arrow is used to represent the motion of a single electron in homolytic bond cleavage. There are two main sources from which radicals can be formed:
Radicals from spin-paired molecules:
Radicals can be obtained from spin-paired molecules either by homolysis or electron transfer. While two radicals are formed in the former, an electron is added in the...
2.5K
Radical Reactivity: Overview01:11

Radical Reactivity: Overview

2.6K
Radicals, the highly reactive species, gain stability by undergoing three different reactions. The first reaction involves a radical-radical coupling, in which a radical combines with another radical, forming a spin‐paired molecule. The second reaction is between a radical and a spin‐paired molecule, generating a new radical and a new spin‐paired molecule. The third reaction is radical decomposition in a unimolecular reaction, forming a new radical and a spin‐paired...
2.6K
Radical Reactivity: Steric Effects01:10

Radical Reactivity: Steric Effects

2.3K
The presence of electron-donating, electron-withdrawing, or conjugating groups adjacent to a radical center, imparts electronic stabilization to the radicals. Examples of such electronically-stabilized radicals are triphenylmethyl, tetramethylpiperidine‐N‐oxide, and 2,2‐diphenyl‐1‐picrylhydrazyl. These radicals are remarkably stable and are known as persistent radicals. Some of the persistent radicals can even be isolated and purified.
Along with electronic...
2.3K

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Updated: Dec 23, 2025

Free Radicals in Chemical Biology: from Chemical Behavior to Biomarker Development
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Method for Structural Determination of Lipid-Derived Radicals.

Yuta Matsuoka1,2, Yoshihiro Izumi2,3, Masatomo Takahashi3

  • 1Physical Chemistry for Life Science Laboratory, Faculty of Pharmaceutical Sciences, Kyushu University, 3-1-1 Maidashi, Higashi-ku, Fukuoka 812-8582, Japan.

Analytical Chemistry
|April 21, 2020
PubMed
Summary

Researchers developed a new method to detect highly reactive lipid radicals, crucial molecules in inflammation and ferroptosis. This technique identified new lipid radicals and provides insights into lipid peroxidation mechanisms.

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Area of Science:

  • Biochemistry
  • Analytical Chemistry
  • Cell Biology

Background:

  • Oxidized lipids drive inflammation and cell death, including ferroptosis.
  • Lipid radicals initiate lipid peroxidation but are difficult to detect due to their reactivity and short half-life.

Purpose of the Study:

  • To develop a novel analytical method for detecting and structurally analyzing lipid-derived radicals.
  • To investigate the role of lipid radicals in lipid peroxidation, inflammation, and ferroptosis.

Main Methods:

  • A combined system of high-performance liquid chromatography fluorometry and high-resolution tandem mass spectrometry was employed.
  • A fluorescent probe was utilized for enhanced detection and structural analysis of lipid radicals.

Main Results:

  • The method successfully detected 132 lipid-derived radicals, including 111 novel species, from five polyunsaturated fatty acids.
  • A database was created to identify the parent fatty acid from radical structures.
  • Twelve endogenous lipid-derived radicals were identified in a mouse model of liver cancer.

Conclusions:

  • The developed method offers a powerful tool for studying lipid peroxidation.
  • This approach provides new insights into the mechanisms of lipid peroxidation-associated inflammation and ferroptosis.
  • The findings have implications for understanding and potentially treating diseases linked to oxidative stress.