A divinyl ether oxylipin
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Etheroleic Acid

Item No. 10005119

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
12-[(1E)-1-hexenyloxy]-9Z,11E-dodecadienoic acid
CAS Number
169217-38-3
Synonyms
  • FA 18:3;O
Molecular Formula
C18H30O3
Formula Weight
294.4
Purity
≥98%
Formulation (Request formulation change)
A solution in ethanol
Solubility(Learn about Variance in Solubility)
Ethanol: soluble
SMILES
CCCC/C=C/O/C=C/C=C\CCCCCCCC(O)=O
InChi Code
InChI=1S/C18H30O3/c1-2-3-4-13-16-21-17-14-11-9-7-5-6-8-10-12-15-18(19)20/h9,11,13-14,16-17H,2-8,10,12,15H2,1H3,(H,19,20)/b11-9-,16-13+,17-14+
InChi Key
NQNHRHWFZHFAAH-XSWVPMOFSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    25 µg

    $181

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    50 µg

    $343

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    Product Description

    Etheroleic acid is a divinyl ether oxylipin.1,2 It is a metabolite of linolenic acid that is formed in plants via 13-lipoxygenase-mediated formation of 13(S)-HpODE (Item No. 48610) or (±)13-HpODE (Item No. 10704) followed by conversion to the divinyl ether by divinyl ether synthase. Etheroleic acid (30 µM) is fungicidal against the powdery mildew B. graminis on the second leaves of barley seedlings.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Grechkin, A.N., Ilyasov, A.V., and Hamberg, M. On the mechanism of biosynthesis of divinyl ether oxylipins by enzyme from garlic bulbs. Eur. J. Biochem. 245(1), 137-142 (1997).

    2. Hamberg, M. Biosynthesis of new divinyl ether oxylipins in Ranunculus plants. Lipids 37(4), 427-433 (2002).

    3. Cowley, T., and Walters, D. Local and systemic effects of oxylipins on powdery mildew infection in barley. Pest Manag. Sci. 61(6), 572-576 (2005).