Related Experiment Video
Updated: Aug 7, 2026

Free Radicals in Chemical Biology: from Chemical Behavior to Biomarker Development
Published on: April 15, 2013
Radiolytic transformation of 2,2',4'-trihydroxychalcone
Redouane Mokrini1, Patrick Trouillas, Mourad Kaouadji
1EA 1085 "Biomolécules et Cibles Cellulaires Tumorales," 87025 Limoges Cedex, France.
Abstract:
Radiolysis of 2,2',4'-trihydroxychalcone, a natural antioxidant present in fruit and vegetables, was performed in ethanol in the absence or in the presence of dioxygen. The degradation process of chalcone was followed in de-aerated solution by HPLC, NMR, FAB-LSIMS mass spectroscopy and analytical TLC. Under anaerobic conditions, six new products (three couples of diastereoisomers) were identified. Four of them kept the chalcone skeleton with OCH(2)CH(3), CH(OH)CH(3) and H substitutions on C(alpha) and C(beta). Thus the target was the alpha-beta double bond on which ethanol radicals were added. The two other compounds were formed in a second stage and exhibited a cyclization between the substituent on C(beta) and the carbonyl group. In the presence of dioxygen, these reactions were prevented and chalcone was protected. This study was the first step toward understanding of the behavior chalcone in irradiated fruits and vegetables.
More Related Videos
09:20Perturbing Endothelial Biomechanics via Connexin 43 Structural Disruption
Published on: October 4, 2019
06:31Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
Published on: November 27, 2015
Related Concept Videos
Radical Halogenation: Stereochemistry
Halogenation to form a new chiral center:
Photochemical Electrocyclic Reactions: Stereochemistry
Selection Rules: Photochemical Activation
Preparation of Diols and Pinacol Rearrangement
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration
Prochirality
Phase II Reactions: Miscellaneous Conjugation Reactions
A key example involves the conjugation of cyanide ions, which impair cellular respiration and alter hemoglobin into non-oxygen-carrying cyanmethemoglobin. To neutralize this threat, a sulfur atom from thiosulphate is transferred to the cyanide ion, catalyzed by the enzyme rhodanese, resulting in an inactive compound called thiocyanate. The production of...