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13-epi-12-oxo Phytodienoic Acid Exclusive

Cayman Chemical Item Number 10195

13-epi-12-oxo PDA (CAS 71606-07-0)

13-epi-12-oxo Phytodienoic Acid (CAS 71606-07-0)

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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.

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 1 1981-1991 (1991).

2 Hamberg, M., and Gardner, H.W. Oxylipin pathway to jasmonates: Biochemistry and biological significance. Biochim Biophys Acta 1165 1-18 (1992).

Synonyms
  • 13-epi-12-oxo PDA
Formal Name 4-​oxo-​5R-​(2Z)-​2-​pentenyl-​2-​cyclopentene-​1S-​octanoic acid
CAS Number 71606-07-0
Molecular Formula C18H28O3
Formula Weight 292.4
Formulation A solution in ethanol
Purity >95%
λmax 220 nm
Stability 1 year
Storage -80°C
Shipping Dry ice in continental US; may vary elsewhere
SMILES
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CC/C=C\C[C@@H]​(C(C=C1)​=O)​[C@H]​1CCCCCCCC(O)​=O

Background Reading

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 1 1981-1991 (1991).

Hamberg, M., and Gardner, H.W. Oxylipin pathway to jasmonates: Biochemistry and biological significance. Biochim Biophys Acta 1165 1-18 (1992).

13-epi-12-oxo Phytodienoic Acid is available in the following screening library:

Size Price Quantity Subtotal
100 µg $44.00 $0.00
500 µg $198.00 $0.00
1 mg $352.00 $0.00
5 mg $1,540.00 $0.00
Bulk Contact
Cart Total $0.00

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Pricing updated 2012-05-26. Prices are subject to change without notice.

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Warning This product is not for human or veterinary use.

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