| Identification | Back Directory | [Name]
13-EPI-12-OXO PDA | [CAS]
71606-07-0 | [Synonyms]
13-EPI-12-OXO PDA
3-epi-12-oxo Phytodienoic Acid
13-EPI-12-OXO PHYTODIENOIC ACID
4-OXO-5R-(2Z)-2-PENTENYL-2-CYCLOPENTENE-1S-OCTANOIC ACID
2-Cyclopentene-1-octanoic acid, 4-oxo-5-(2Z)-2-penten-1-yl-, (1S,5R)-
8-((1S,5R)-4-oxo-5-((Z)-pent-2-en-1-yl)cyclopent-2-en-1-yl)octanoic acid | [Molecular Formula]
C18H28O3 | [MDL Number]
MFCD08062231 | [MOL File]
71606-07-0.mol | [Molecular Weight]
292.41 |
| Hazard Information | Back Directory | [Description]
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. | [Definition]
ChEBI: 9s,13r-12-Oxophytodienoic Acid is a prostanoid. | [References]
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). |
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