A plant polyphenol
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Isomer(s)
33806Naringenin Chalcone
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Butein

Item No. 15371

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2E)-1-(2,4-dihydroxyphenyl)-3-(3,4-dihydroxyphenyl)-2-propen-1-one
CAS Number
487-52-5
Synonyms
  • 2’,3,4,4’-tetrahydroxy Chalcone
Molecular Formula
C15H12O5
Formula Weight
272.3
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 25 mg/mlDMF:PBS(pH 7.2)(1:1): 0.5 mg/mlDMSO: 20 mg/mlEthanol: 20 mg/ml
λmax
262, 348, 382 nm
SMILES
OC1=C(O)C=CC(/C=C/C(C2=C(O)C=C(O)C=C2)=O)=C1
InChi Code
InChI=1S/C15H12O5/c16-10-3-4-11(14(19)8-10)12(17)5-1-9-2-6-13(18)15(20)7-9/h1-8,16,18-20H/b5-1+
InChi Key
AYMYWHCQALZEGT-ORCRQEGFSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $36

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    10 mg

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    Product Description

    Butein is a plant polyphenol that is classified as a chalcone, due to the propenone linkage between the phenol groups. Like other polyphenols, butein is a potent antioxidant and affects the numerous pathways modulated by oxidant tone, including inflammation, cancer, and immune response.1,2,3 It inhibits 5-lipoxygenase, the enoyl-acyl-carrier protein reductase of P. falciparum, angiotensin-converting enzyme, and Src kinase (IC50 or Ki values of 0.01, 2.97, 0.73, and 65 μM, respectively).4,5,6,7 Butein is also a sirtuin activator, increasing trichostatin A (Item No. 89730)-insensitive deacetylase activity.8,9

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Yadav, V.R., Prasad, S., Sung, B., et al. The role of chalcones in suppression of NF-κB-mediated inflammation and cancer. Int. Immunopharmacol. 11(3), 295-309 (2011).

    2. Lee, E.H., Song, D.G., Lee, J.Y., et al. Inhibitory effect of the compounds isolated from Rhus verniciflua on aldose reductase and advanced glycation endproducts. Biol. Pharm. Bull. 31(8), 1626-1630 (2008).

    3. Gupta, S.C., Kim, J.H., Prasad, S., et al. Regulation of survival, proliferation, invasion, angiogenesis, and metastasis of tumor cells through modulation of inflammatory pathways by nutraceuticals. Cancer Metastasis Rev. 29(3), 405-434 (2010).

    4. Sogawa, S., Nihro, Y., Ueda, H., et al. 3,4-Dihydroxychalcones as potent 5-lipoxygenase and cyclooxygenase inhibitors. J. Med. Chem. 36(24), 3904-3909 (1993).

    5. Sharma, S.K., Parasuraman, P., Kumar, G., et al. Green tea catechins potentiate triclosan binding to enoyl-ACP reductase from Plasmodium falciparum (PfENR). J. Med. Chem. 50(4), 765-775 (2007).

    6. Bonesi, M., Loizzo, M.R., Statti, G.A., et al. The synthesis and angiotensin converting enzyme (ACE) inhibitory activity of chalcones and their pyrazole derivatives. Bioorg. Med. Chem. Lett. 20(6), 1990-1993 (2010).

    7. McArdle, B.M., Campitelli, M.R., and Quinn, R.J. A common protein fold topology shared by flavonoid biosynthetic enzymes and therapeutic targets. J. Nat. Prod. 69(1), 14-17 (2006).

    8. Wood, J.G., Rogina, B., Lavu, S., et al. Sirtuin activators mimic caloric restriction and delay ageing in metazoans. Nature 430, 686-689 (2004).

    9. Szczepankiewicz, B.G., and Ng, P.Y. Sirtuin modulators: Targets for metabolic diseases and beyond. Curr. Top. Med. Chem. 8(17), 1533-1544 (2008).