A lipoxygenase metabolite of α-linolenic acid
Related Products
Diastereomer(s)
8852012-oxo Phytodienoic Acid
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13-epi-12-oxo Phytodienoic Acid

Item No. 10195

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-oxo-5R-(2Z)-2-pentenyl-2-cyclopentene-1S-octanoic acid
CAS Number
71606-07-0
Synonyms
  • 13-epi-12-oxo PDA
Molecular Formula
C18H28O3
Formula Weight
292.4
Purity
≥95%
Formulation (Request formulation change)
A 1 mg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 10 mg/mlEthanol: 100 mg/mlPBS (pH 7.2): 1 mg/ml
λmax
220 nm
SMILES
CC/C=C\C[C@@H](C(C=C1)=O)[C@H]1CCCCCCCC(O)=O
InChi Code
InChI=1S/C18H28O3/c1-2-3-7-11-16-15(13-14-17(16)19)10-8-5-4-6-9-12-18(20)21/h3,7,13-16H,2,4-6,8-12H2,1H3,(H,20,21)/b7-3-/t15-,16+/m0/s1
InChi Key
PMTMAFAPLCGXGK-TTXFDSJOSA-N
Shipping & Storage Information
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
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    100 µg

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    Product 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.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description 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. J. Chem. Soc. Perkin Trans. 1 8, 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).