13-EPI-12-OXO PDA

13-epi-12-oxo Phytodienoic acid (13-epi-12-oxo PDA) is a lipoxygenase metabolite of α-linolenic acid in the leaves of green plants such as corn. ω-3 and ω-6 polyunsaturated fatty acids in plants are substrates for plant lipoxygenases.¹ 12-oxo PDA is one of the best studied end metabolites of this enzymatic pathway.² While the initial enzymatic product and major isomer of 12-oxo PDA contains side chains in the cis position, both being β to the ring, the upper side chain attached at C-13, can and frequently does, isomerize when 12-oxo PDA is extracted, isolated, or stored. 13-epi-12-oxo PDA is the product of this isomerization.

ChEBI: 9s,13r-12-Oxophytodienoic Acid is a prostanoid.

1. Crombie, L., and Mistry, K.M. Synthesis of 12-oxophytodienoic acid (12-oxoPDA) and the compounds of its enzymic degradation cascade in plants, OPC-8:0, -6:0, -4:0 and -2:0 (epi-jasmonic acid), as their methyl esters Journal of the Chemical Society 1,1981-1991(1991).
2. Hamberg, M., and Gardner, H.W. Oxylipin pathway to jasmonates: Biochemistry and biological significance Biochim. Biophys. Acta 1165(1),1-18(1992).