A potent activator of Nrf2
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2-Trifluoromethyl-2'-methoxychalcone

Item No. 11881

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1-(2-methoxyphenyl)-3-[2-(trifluoromethyl)phenyl]-2E-propen-1-one
CAS Number
1309371-03-6
Molecular Formula
C17H13F3O2
Formula Weight
306.3
Purity
≥98%
Formulation
A 10 mg/ml solution in methyl acetate
Solubility(Learn about Variance in Solubility)
DMF: 14 mg/mlDMF:PBS (pH 7.2)(1:3): 0.25 mg/mlDMSO: 5 mg/mlEthanol: 11 mg/ml
λmax
219, 288 nm
SMILES
COC1=C(C(/C=C/C2=CC=CC=C2C(F)(F)F)=O)C=CC=C1
InChi Code
InChI=1S/C17H13F3O2/c1-22-16-9-5-3-7-13(16)15(21)11-10-12-6-2-4-8-14(12)17(18,19)20/h2-11H,1H3/b11-10+
InChi Key
BDZOPPCXQXPRKH-ZHACJKMWSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

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    10 mg

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    50 mg

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    100 mg

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    Cayman Chemical
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    Product Description

    Nrf2 activation is central to cytoprotective gene expression against oxidative and/or electrophilic stress.1 Unless activated by inflammatory, environmental, or oxidative stressors, Nrf2 is sequestered in the cytoplasm by its repressor, Keap1.2 Because of its protective capabilities, small molecules that activate Nrf2 signaling are being examined as potential anti-cancer or anti-inflammatory agents.3 2-Trifluoromethyl-2'-methoxychalcone is a potent activator of Nrf2, both in vitro and in mice.4 Human bronchial epithelial cells treated with 10 μM 2-trifluoromethyl-2'-methoxychalcone showed a marked increase in the expression of the Nrf2-regulated antioxidant genes, GCLM and NQO1. Furthermore, treatment of mice with 50 mg/kg 2-trifluoromethyl-2’-methoxychalcone leads to a 4.5- and 4.6-fold increase in the expression of GCLM and NQO1, respectively, in the small intestine.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Wang, R., Kern, J.T., Goodfriend, T.L., et al. Activation of the antioxidant response element by specific oxidized metabolites of linoleic acid. Prostaglandins Leukot. Essent. Fatty Acids 81(1), 53-59 (2009).

    2. Gao, L., Wang, J., Sekhar, K.R., et al. Novel n-3 fatty acid oxidation products activate Nrf2 by destabilizing the association between Keap1 and Cullin3. The Journal of Biological Chemisty 282(4), 2529-2537 (2007).

    3. Taguchi, K., Motohashi, H., and Yamamoto, M. Molecular mechanisms of the Keap1-Nrf2 pathway in stress response and cancer evolution. Genes Cells 16(2), 123-140 (2011).

    4. Kumar, V., Kumar, S., Hassan, M., et al. Novel chalcone derivatives as potent Nrf2 activators in mice and human lung epithelial cells. J. Med. Chem. 54(12), 4147-4159 (2011).