An isoprostane formed from α-linolenic acid in plants
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A1-Phytoprostane-I

Item No. 9000593

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-(3-hydroxy-1-penten-1-yl)-5-oxo-3-cyclopentene-1-octanoic acid
CAS Number
1035557-09-5
Synonyms
  • 16-A1-Phytoprostane
  • Phytoprostane A1
  • PPA1
Molecular Formula
C18H28O4
Formula Weight
308.4
Purity
≥90% (trans isomer mix)
Formulation (Request formulation change)
A 1 mg/ml solution in methyl acetate
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 20 mg/mlDMSO:PBS(pH7.2) (1:1): 0.5 mg/mlEthanol: 10 mg/ml
λmax
217 nm
SMILES
O=C1C(CCCCCCCC(O)=O)C(/C=C/C(O)CC)C=C1
InChi Code
InChI=1S/C18H28O4/c1-2-15(19)12-10-14-11-13-17(20)16(14)8-6-4-3-5-7-9-18(21)22/h10-16,19H,2-9H2,1H3,(H,21,22)/b12-10+
InChi Key
OXXJZDJLYSMGIQ-ZRDIBKRKSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    100 µg

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    Product Description

    A1-Phytoprostane-I is a cyclopentenone isoprostane produced by the action of reactive oxygen species on α-linolenic acid in plants.1,2,3 There are two A1-phytoprostanes, both having the single ketone group on the ring structure. This isoform results from cyclization between carbons 9 and 13 of linolenic acid, as opposed to carbons 3 and 7 in A1-phytoprostane-II. A1-Phytoprostanes induce the expression of glutathione-S-transferase, increase phytoalexin biosynthesis, and trigger the expression of several genes involved in primary and secondary metabolism in plants.1,4,3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Thoma, I., Loeffler, C., Sinha, A.K., et al. Cyclopentenone isoprostanes induced by reactive oxygen species trigger defense gene activation and phytoalexin accumulation in plants. Plant J. 34(3), 363-375 (2003).

    2. Jahn, U., Galano, J.M., and Durand, T. Beyond prostaglandins--chemistry and biology of cyclic oxygenated metabolites formed by free-radical pathways from polyunsaturated fatty acids. Angew. Chem. Int. Ed. Engl. 47, 5894-5955 (2008).

    3. Mueller, M.J., and Berger, S. Reactive electrophilic oxylipins: Pattern recognition and signalling. Phytochemistry 70, 1511-1521 (2009).

    4. Dueckershoff, K., Mueller, S., Mueller, M.J., et al. Impact of cyclopentenone-oxylipins on the proteome of Arabidopsis thaliana. Biochim. Biophys. Acta 1784, 1975-1985 (2008).