A metabolite of DHA with anti-inflammatory properties
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17-oxo-4(Z),7(Z),10(Z),13(Z),15(E),19(Z)-Docosahexaenoic Acid

Item No. 9000346

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4Z,7Z,10Z,13Z,15E,19Z-17-oxo-docosapentaenoic acid
CAS Number
1233715-28-0
Synonyms
  • EFOX
  • 17-oxo-4(Z),7(Z),10(Z),13(Z),15(E),19(Z)-DHA
  • 17-oxo-DHA
Molecular Formula
C22H30O3
Formula Weight
342.5
Purity
≥90%
Formulation
A 100 µg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
DMF: 15 mg/mlDMSO: 10 mg/mlEthanol: 20 mg/ml
λmax
281 nm
SMILES
CC/C=C\CC(=O)/C=C\C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O
InChi Code
InChI=1S/C22H30O3/c1-2-3-15-18-21(23)19-16-13-11-9-7-5-4-6-8-10-12-14-17-20-22(24)25/h3,5-8,11-16,19H,2,4,9-10,17-18,20H2,1H3,(H,24,25)/b7-5-,8-6-,13-11-,14-12-,15-3-,19-16+
InChi Key
QCEBQMMZCFADMF-VIIQGJSXSA-N
Shipping & Storage Information
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
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    25 µg

    $54

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    50 µg

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    100 µg

    $190

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    250 µg

    $418

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    Product Description

    17-oxo-4(Z),7(Z),10(Z),13(Z),15(E),19(Z)-Docosahexaenoic acid is a metabolite of lipoxygenase-mediated oxidation of DHA that is produced endogenously by aspirin-enhanced COX-2 activity.1,2,3 It has been shown to activate Nrf2-dependent antioxidant gene expression, to act as a PPARγ agonist (EC50 = ~200 nM), and to inhibit pro-inflammatory cytokine and nitric oxide production at biological concentration ranges (5-25 µM).3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Butovich, I.A. A one-step method of 10,17-dihydro(pero)xydocosahexa-4Z,7Z,11E,13Z,15E,19Z-enoic acid synthesis by soybean lipoxygenase. J. Lipid Res. 47, 854-863 (2006).

    2. Jie, M.S.F.L.K., and Pasha, M.K. Fatty acids, fatty acid analogues and their derivatives. Nat. Prod. Rep. 607-629 (1998).

    3. Groeger, A.L., Cipollina, C., Cole, M.P., et al. Cyclooxygenase-2 generates anti-inflammatory mediators from omega-3 fatty acids. Nat. Chem. Biol. (2010).