An active metabolite of docosahexaenoic acid
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4-oxo Docosahexaenoic Acid

Item No. 21373

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-oxo-5E,7Z,10Z,13Z,16Z,19Z-docosahexaenoic acid
CAS Number
845673-74-7
Synonyms
  • 4-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: 50 mg/mlDMSO: 50 mg/mlEthanol: 50 mg/mlPBS (pH 7.2): 0.1 mg/ml
λmax
277 nm
SMILES
CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C=C\C(CCC(O)=O)=O
InChi Code
InChI=1S/C22H30O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-21(23)19-20-22(24)25/h3-4,6-7,9-10,12-13,15-18H,2,5,8,11,14,19-20H2,1H3,(H,24,25)/b4-3-,7-6-,10-9-,13-12-,16-15-,18-17+
InChi Key
UHNUULCIKILOHW-PQVBWYSWSA-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

    4-oxo Docosahexaenoic acid is an active metabolite of docosahexaenoic acid (Item No. 90310).1 It is formed from docosahexaenoic acid by 5-lipoxygenase (5-LO). 4-oxo Docosahexaenoic acid is an agonist of peroxisome proliferator-activated receptor γ (PPARγ).2 It induces gene transcription in a reporter assay using COS-1 cells expressing PPARγ (EC50 = ~10 µM). 4-oxo Docosahexaenoic acid (100 µM) decreases the proliferation of MDA-MB-231, BT-549, T47D, and SK-BR-3 breast cancer cells, MCF-10F breast epithelial cells, and increases the proliferation of MCF-7 breast cancer cells.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Chen, K.-M., Thompson, H., Vanden-Heuvel, J.P., et al. Lipoxygenase catalyzed metabolites derived from docosahexaenoic acid are promising antitumor agents against breast cancer. Sci. Rep. 11(1), 410 (2021).

    2. Itoh, T., Fairall, L., Amin, K., et al. Structural basis for the activation of PPARγ by oxidized fatty acids. Nat. Struct. Mol. Biol. 15(9), 924-931 (2008).

    3. Pogash, T.J., El-Bayoumy, K., Amin, S., et al. Oxidized derivative of docosahexaenoic acid preferentially inhibit cell proliferation in triple negative over luminal breast cancer cells. In Vitro Cell. Dev. Biol. Anim. 51(2), 121-127 (2015).