A flavonoid with diverse biological activities
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Isomer(s)
15371Butein 14173Naringenin
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Naringenin Chalcone

Item No. 33806

Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)-2-propen-1-one
CAS Number
73692-50-9
Synonyms
  • 2',4,4',6'-Tetrahydroxychalcone
Molecular Formula
C15H12O5
Formula Weight
272.3
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 15 mg/mlDMSO: 10 mg/mlEthanol: 1 mg/mlPBS (pH 7.2): slightly soluble
λmax
366 nm
SMILES
O=C(C1=C(O)C=C(O)C=C1O)C=CC2=CC=C(C=C2)O
InChi Code
InChI=1S/C15H12O5/c16-10-4-1-9(2-5-10)3-6-12(18)15-13(19)7-11(17)8-14(15)20/h1-8,16-17,19-20H
InChi Key
YQHMWTPYORBCMF-UHFFFAOYSA-N
Origin
Plant/Citrus maxima peel
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    500 µg

    $103

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    1 mg

    $183

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    5 mg

    $602

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    Product Description

    Naringenin chalcone is a flavonoid that has been found in the skin of red tomatoes and has diverse biological activities.1,2,3 It inhibits the proliferation of SENCAR mouse skin transformed (SST) cells and SENCAR mouse skin transformed tumor (SST-T) cells (IC50s = 92 and 184 µg/ml).1 Naringenin chalcone (50 µg/animal) reduces the number of papillomas in a mouse model of skin carcinogenesis induced by phorbol 12-myristate 13-acetate (TPA; Item No. 10008014). Topical administration of naringenin chalcone reduces ear edema in a mouse model of TPA-induced inflammation.2 Naringenin chalcone (0.8 mg/kg) reduces airway hyperresponsiveness, bronchoalveolar lavage fluid (BALF) eosinophil infiltration, and lung mucus production in a mouse model of ovalbumin-induced allergic asthma.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Yagura, T., Motomiya, T., Ito, M., et al. Anticarcinogenic compounds in the Uzbek medicinal plant, Helichrysum maracandicum. J. Nat. Med. 62(2), 174-178 (2008).

    2. Escribano-Ferrer, E., Regué, J.Q., Garcia-Sala, X., et al. In vivo anti-inflammatory and antiallergic activity of pure naringenin, naringenin chalcone, and quercetin in mice. J. Nat. Prod. 82(2), 177-182 (2019).

    3. Iwamura, C., Shinoda, K., Yoshimura, M., et al. Naringenin chalcone suppresses allergic asthma by inhibiting the type-2 function of CD4 T cells. Allergol. Int. 59(1), 67-73 (2010).