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Updated: Jan 19, 2026

Free Radicals in Chemical Biology: from Chemical Behavior to Biomarker Development
Published on: April 15, 2013
Stereochemistry of Linoleic Acid Esters of Hydroxy Linoleic Acids
Huijing Wang1, Matthew J Kolar2, Tina Chang2
1Skaggs School of Pharmacy and Pharmaceutical Sciences , UC San Diego , 9500 Gilman Drive , La Jolla , California 92093-0934 , United States.
Abstract:
The syntheses of linoleic acid esters of hydroxy linoleic acids (LAHLAs) present in oat oil and human serum have been achieved, providing access to material for testing and the determination of the stereochemistry of the natural compounds. While 9- and 13-LAHLAs were found to be a mixture of enantiomers 15-LAHLA is generated in a single optical form in oat oil. The stereochemistry of 15-LAHLA in oat oil was found to be opposite to that reported for digalactosyldiacylglycerol that possesses an embedded 15-LAHLA.
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