Abstract
We studied new conjugated carbonyls with a hydroxypentanone ring like that of prostaglandin and capable of producing reddish pigments λmax 510-520nm) by reaction with amino acids. The carbonyls derived from autoxidation of ethyl eicosapentaenoate were purified successively by column chromatography on Sephadex LH-20 and Silicagel 60, and by HPLC. Using GC-MS analysis, four out of the six carbonyls, predicted from the formation mechanism for prostaglandin-like substances, were identified to be 3-(5-hydroxy-3-oxo-2-pent-2-enylcyclopentyl)-2-propenal, 3-(2-ethyl-5-hydroxy-3-oxocyclopentyl)-2-propenal, ethyl 4-[2-(2-formylvinyl)-3-hydroxy-5-oxocyclo-pentyl]butanoate, and ethyl 7-[2-(2-formylvinyl)-3-hydroxy-5-oxocyclopentyl]hept-5-enoate.
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