An oxylipin
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Colneleic Acid

Item No. 10005076

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
9-[(1E,3Z)-1,3-nonadien-1-yloxy]-8E-nonenoic acid
CAS Number
52761-34-9
Synonyms
  • FA 18:3;O
Molecular Formula
C18H30O3
Formula Weight
294.4
Purity
≥98%
Formulation
A solution in ethanol
Solubility(Learn about Variance in Solubility)
Ethanol: soluble
SMILES
CCCCC/C=C\C=C\OCCCCCCCCC(O)=O
InChi Code
InChI=1S/C18H32O3/c1-2-3-4-5-7-10-13-16-21-17-14-11-8-6-9-12-15-18(19)20/h7,10,13,16H,2-6,8-9,11-12,14-15,17H2,1H3,(H,19,20)/b10-7-,16-13+
InChi Key
VWZHOYQVPMQSEL-YTLDOUCOSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    100 µg

    $380

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    Product Description

    Colneleic acid is a divinyl ether oxylipin and an active metabolite of linoleic acid (Item Nos. 90150 | 90150.1 | 21909) that has been found in potatoes. 1,2,3,4 It is formed from linoleic acid by 9-lipoxygenase (9-LO) via a (±)9-HpODE (Item No. 10705) intermediate and divinyl ether synthase.1,2 Colneleic acid decreases P. infestans hyphae growth when used at concentrations of 15, 75, and 150 µM and reduces P. infestans cystospore germination in a concentration-dependent manner.3 The levels of colneleic acid are increased in potato leaves following P. infestans infection and in rice seedlings following brown planthopper feeding.3,4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Galliard, T., and Phillips, D.R. The enzymic conversion of linoleic acid into 9-(nona-1',3'-dienoxy)non-8-enoic acid, a novel unsaturated ether derivative isolated from homogenates of Solanum tuberosum tubers. Biochem. J. 129, 743-753 (1972).

    2. Fahlstadius, P., and Hamberg, M. Stereospecific removal of the pro-R hydrogen at C-8 of (9S)-hydroperoxyoctadecadienoic acid in the biosynthesis of colneleic acid. J. Chem. Soc. Perkin 1 1, 2027-2030 (1990).

    3. Weber, H., Chételat, A., Caldelari, D., et al. Divinyl ether fatty acid synthesis in late blight-diseased potato leaves. Plant Cell 11(3), 485-494 (1999).

    4. Wang, R., Shen, W., Liu, L., et al. A novel lipoxygenase gene from developing rice seeds confers dual position specificity and responds to wounding and insect attack. Plant Mol. Biol. 66(4), 401-414 (2008).