Stereochemical Assignment of Conjugated Carbonyls with a Prostaglandin-like Ring Structure Formed During Autoxidaion of Linolenate

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Conjugated carbonyls each with a prostaglandin-like hydroxycyclopentanone ring were previously shown to form during autoxidation of polyunsaturated fatty acids. The carbonyls are very reactive with amino compounds and form novel red pigments when reacted with amino acids. Two stereoisomers of the carbonyl, 3- (2-ethyl-5-hydroxy-3-oxo) cyclopentyl-2-propenal, were isolated from autoxidized linolenate; their chemical structures were determined and stereochemical assignments made by 1H- and 13C-nuclear magnetic resonance spectroscopy and nuclear Overhauser enhancement experiments. The isomers were shown to have different configurations of the side chains of the hydroxycyclopentanone ring. The major isomer possessed cis ring substituents although natural prostaglandins are known to have trans ring substituents.
Japan Oil Chemists' Societyの論文