An internal standard for the quantification of dinor-OPDA
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dinor-12-oxo Phytodienoic Acid-d5

Item No. 10696

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-oxo-5S-(2Z)-2-penten-4,4,5,5,5-d5-1-yl-2-cyclopentene-1S-hexanoic acid
Synonyms
  • dinor-OPDA-d5
  • dinor-12-oxo PDA-d5
Molecular Formula
C16H19D5O3
Formula Weight
269.4
Purity
≥99% deuterated forms (d1-d5)
Formulation
A 1 mg/ml solution in methanol
Solubility(Learn about Variance in Solubility)
DMF: 25 mg/mlDMSO: 15 mg/mlEthanol: 300 mg/mlPBS (pH 7.2): 3 mg/ml
λmax
220 nm
SMILES
O=C1[C@@H](C/C=C\C([2H])([2H])C([2H])([2H])[2H])[C@@H](CCCCCC(O)=O)C=C1
InChi Code
InChI=1S/C16H24O3/c1-2-3-5-9-14-13(11-12-15(14)17)8-6-4-7-10-16(18)19/h3,5,11-14H,2,4,6-10H2,1H3,(H,18,19)/b5-3-/t13-,14-/m0/s1/i1D3,2D2
InChi Key
SZVNKXCDJUBPQO-UBJGXVEQSA-N
Shipping & Storage Information
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
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    50 µg

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    Product Description

    dinor-12-oxo Phytodienoic acid-d5 (dinor-OPDA-d5) contains five deuterium atoms at the 4, 4', 5, 5, and 5 positions. It is intended for use as an internal standard for the quantification of dinor-OPDA by GC- or LC-mass spectrometry (MS). In plants, certain unsaturated fatty acids are oxygenated and then further modified along the jasmonate pathway to produce plant hormones that are involved in senescence, flower development, mechanotransduction, and the response to herbivory.1 dinor-OPDA is an intermediate in the synthesis of jasmonic acid from hexadecatrienoic acid.2,3 dinor-OPDA can also be incorporated into glycerolipids and galactolipids, including certain arabidopsides.4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Schaller, A., and Stintzi, A. Enzymes in jasmonate biosynthesis - Structure, function, regulation. Phytochemistry 70(13-14), 1532-1538 (2009).

    2. Snoeren, T.A.L., Van Poecke, R.M.P., and Dicke, M. Multidisciplinary approach to unravelling the relative contribution of different oxylipins in indirect defense of Arabidopsis thaliana. J. Chem. Ecol. 35(9), 1021-1031 (2009).

    3. Gfeller, A., Dubugnon, L., Liechti, R., et al. Jasmonate biochemical pathway. Sci. Signal. 3(109), (2010).

    4. Kourtchenko, O., Andersson, M.A., Hamberg, M., et al. Oxo-phytodienoic acid-containing galactolipids in Arabidopsis: Jasmonate signaling dependence. Plant Physiol. 145(4), 1658-1669 (2007).

    5. Buseman, S.M., Tamura, P., Sparks, A.A., et al. Wounding stimulates the accumulation of glycerolipids containing oxophytodienoic acid and dinor-oxophytodienoic acid in Arabidopsis leaves. Plant Physiol. 142(1), 28-39 (2006).