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Join us! · InformexUSA 2012 · New Orleans, Louisiana · February 14-17, 2012 · Booth 2514

13(S)-HpOTrE Exclusive

Cayman Chemical Item Number 45220

(CAS 67597-26-6)

13(S)-HpOTrE (CAS 67597-26-6)

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Description

13(S)-HpOTrE is a monohydroperoxy polyunsaturated fatty acid produced in soybeans by the action of soybean LO-2 on esterified α-linolenic acid.1 Incubation of soybean seedling biomembranes with soybean LO-2 catalyzes the formation of both 9- and 13-HpOTrE in a molar ratio of 10:1.1 In plants, 13(S)-HpOTrE can be metabolized by the hydroperoxide lyase pathway producing aldehyde and oxoacid fragments, or by the hydroperoxide dehydratase pathway producing jasmonic acid.2,3,4 Treatment of tomato leaves with 13-HpOTrE causes induction of proteinase inhibitors, simulating the normal response to wounding.5 This data suggests that in plants 13(S)-HpOTrE may participate in a lipid-based signalling system initiated by insect and pathogen attack.

1 Maccarrone, M., van Aarle, P.G.M., Veldink, G.A., et al. In vitro oxygenation of soybean biomembranes by lipoxygenase-2. Biochim Biophys Acta 1190 164-169 (1994).

2 Vick, B.A. Oxygenated fatty acids of the lipoxygenase pathway. 167-191 (1993).

3 Salch, Y.P., Grove, M.J., Takamura, H., et al. Characterization of a C-5,13-cleaving enzyme of 13(S)-hydroperoxide of linolenic acid by soybean seed. Plant Physiol 108 1211-1218 (1995).

4 Simpson, T.D., and Garnder, H.W. Allene oxide synthase and allene oxide cyclase, enzymes of the jasmonic acid pathway, localized in Glycine max tissues. Plant Physiol 108 199-202 (1995).

5 Farmer, E.E., and Ryan, C.A. Octadecanoid precursors of jasmonic acid activate the synthesis of wound-inducible proteinase inhibitors. Plant Cell 4 129-134 (1992).

Formal Name 13S-​hydroperoxy-​9Z,​11E,​15Z-​octadecatrienoic acid
CAS Number 67597-26-6
Molecular Formula C18H30O4
Formula Weight 310.4
Formulation A solution in ethanol
Purity ≥98%
λmax 235 nm
ε 23
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]​(OO)​/C=C/C=C\CCCCCCCC(O)​=O

Background Reading

Vick, B.A. Oxygenated fatty acids of the lipoxygenase pathway. 167-191 (1993).

Simpson, T.D., and Garnder, H.W. Allene oxide synthase and allene oxide cyclase, enzymes of the jasmonic acid pathway, localized in Glycine max tissues. Plant Physiol 108 199-202 (1995).

Farmer, E.E., and Ryan, C.A. Octadecanoid precursors of jasmonic acid activate the synthesis of wound-inducible proteinase inhibitors. Plant Cell 4 129-134 (1992).

Salch, Y.P., Grove, M.J., Takamura, H., et al. Characterization of a C-5,13-cleaving enzyme of 13(S)-hydroperoxide of linolenic acid by soybean seed. Plant Physiol 108 1211-1218 (1995).

Maccarrone, M., van Aarle, P.G.M., Veldink, G.A., et al. In vitro oxygenation of soybean biomembranes by lipoxygenase-2. Biochim Biophys Acta 1190 164-169 (1994).

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13(S)-HpOTrE is available in the following screening library:

Size Price Quantity Subtotal
100 µg $42.00 $0.00
500 µg $189.00 $0.00
1 mg $336.00 $0.00
5 mg $1,470.00 $0.00
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Cart Total $0.00

This product is available in custom sizes and/or larger quantities.

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Pricing updated 2012-02-11. 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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α-Linolenic Acid-d14
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