A PPARγ agonist
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15-deoxy-Δ12,14-Prostaglandin J2

Item No. 18570

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
11-oxo-prosta-5Z,9,12E,14E-tetraen-1-oic acid
CAS Number
87893-55-8
Synonyms
  • 15-deoxy-Δ12,14-PGJ2
Molecular Formula
C20H28O3
Formula Weight
316.4
Purity
≥95%
Formulation (Request formulation change)
A 1 mg/ml solution in methyl acetate
Solubility(Learn about Variance in Solubility)
DMF: >100 mg/mlDMSO: >20 mg/mlEthanol: >75 mg/mlPBS (pH 7.2): 2 mg/ml
λmax
229, 306 nm
SMILES
O=C1/C([C@@H](C/C=C\CCCC(O)=O)C=C1)=C/C=C/CCCCC
InChi Code
InChI=1S/C20H28O3/c1-2-3-4-5-6-10-13-18-17(15-16-19(18)21)12-9-7-8-11-14-20(22)23/h6-7,9-10,13,15-17H,2-5,8,11-12,14H2,1H3,(H,22,23)/b9-7-,10-6+,18-13+/t17-/m0/s1
InChi Key
VHRUMKCAEVRUBK-GODQJPCRSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    Product Description

    15-deoxy-Δ12,14-Prostaglandin J2 (15-deoxy-Δ12,14-PGJ2) is formed from PGD2 by the elimination of two molecules of water. It binds selectively to PPARγ with an EC50 value of 2 µM in a murine chimera system.1,2 15-deoxy-Δ12,14-PGJ2 is more potent than PGD2, Δ12-PGJ2, and PGJ2 in stimulating lipogenesis in C3H10T1/2 cells. The EC50 for induction of adipocyte differentiation in cultured fibroblasts is 7 µM.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kliewer, S.A., Lenhard, J.M., Willson, T.M., et al. A prostaglandin J2 metabolite binds peroxisome proliferator-activated receptor γ and promotes adipocyte differentiation. Cell 83(5), 813-819 (1995).

    2. Forman, B.M., Tontonoz, P., Chen, J., et al. 15-Deoxy-Δ12,14-prostaglandin J2 is a ligand for the adipocyte determination factor PPARγ. Cell 83(5), 803-812 (1995).

    Product Citations

    Pang, Y., Liu, X., Zhao, C., et al. LC-MS/MS-based arachidonic acid metabolomics in acute spinal cord injury reveals the upregulation of 5-LOX and COX-2 products. Free Radic. Biol. Med. 193(Pt 1), 363-372 (2022).

    Meriwether, D., Sulaiman, D., Volpe, C., et al. Apolipoprotein A-I mimetics mitigate intestinal inflammation in COX2-dependent inflammatory bowel disease model. J. Clin. Invest. 130, 3670-3685 (2019).

    Abis, G., Charles, R.L., Kopec, J., et al. 15-deoxy-D12,14-Prostaglandin J2 inhibits human soluble epoxide hydrolase by a dual orthosteric and allosteric mechanism. Commun. Biol. 2, 188 (2019).

    Sorgi, C.A., Peti, A.P.F., Petta, T., et al. Comprehensive high-resolution multiple-reaction monitoring mass spectrometry for targeted eicosanoid assays. Sci. Data 5, 180167 (2018).

    Reddy, A.T., Lakshmi, S.P., Banno, A., et al. Identification and Molecular Characterization of PPARδ as a Novel Target for Covalent Modification by 15-deoxy-Δ12, 14-prostaglandin J2. ACS Chem. Biol. (2018).

    Grabocka, E., and Bar-Sagi, D. Mutant KRAS enhances tumor cell fitness by upregulating stress granules. Cell 167(7), 1803-1813 (2016).

    Gomez-Abellan, V., Montero, J., Lopez-Munoz, A., et al. Professional phagocytic granulocyte-derived PGD2 regulates the rsolution of inflammation in fish. Develop. Comp. Immunol. 52(2), 182-191 (2015).

    Schröder, R., Xue, L., Konya, V., et al. PGH1, the precursor for the anti-inflammatory prostaglandins of the 1-series, is a potent activator of the pro-inflammatory receptor CRTH2/DP2. PLoS One 7(3), e33329 (2012).