A natural prenylated chalcone with diverse biological activities
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Isoxanthohumol

Item No. 23233

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2,3-dihydro-7-hydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methyl-2-buten-1-yl)-4H-1-benzopyran-4-one
CAS Number
521-48-2
Synonyms
  • IX
  • IXN
Molecular Formula
C21H22O5
Formula Weight
354.4
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 3 mg/mlDMSO: 2.5 mg/mlDMSO:PBS(pH 7.2) (1:3): 0.25 mg/mlEthanol: 3 mg/ml
λmax
289 nm
SMILES
OC1=CC(OC)=C(C(CC(C2=CC=C(O)C=C2)O3)=O)C3=C1C/C=C(C)/C
InChi Code
InChI=1S/C21H22O5/c1-12(2)4-9-15-16(23)10-19(25-3)20-17(24)11-18(26-21(15)20)13-5-7-14(22)8-6-13/h4-8,10,18,22-23H,9,11H2,1-3H3
InChi Key
YKGCBLWILMDSAV-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $39

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    1 mg

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    5 mg

    $270

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    Product Description

    Isoxanthohumol is a natural, prenylated chalcone isolated from the hop plant, H. lupulus (hops). It has diverse biological activities, including antiproliferative, anti-inflammatory, and antiviral properties.1 In B16 and A375 melanoma cells, isoxanthohumol inhibits proliferation (IC50s = 22.15 and 22.9 µM in an MTT assay), slows cell division, and induces apoptosis.2 Isoxanthohumol reversibly inhibits Kv1.3 channels with an EC50 value of 7.8 µM in human Jurkat T cells using patch clamp electrophysiology.3 It has also been used as a marker of beer consumption.4 Isoxanthohumol is metabolized in the liver and intestine to 8-prenylnaringenin (Item No. 17462), a potent phytoestrogen.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Żołnierczyk, A.K., Mączka, W.K., Grabarczyk, M., et al. Isoxanthohumol--Biologically active hop flavonoid. Fitoterapia 103, 71-82 (2015).

    2. Krajnović, T., Kaluđerović, G.N., Wessjohann, L.A., et al. Versatile antitumor potential of isoxanthohumol: Enhancement of paclitaxel activity in vivo. Pharmacol. Res. 105, 62-73 (2016).

    3. Gąsiorowska, J., Teisseyre, A., Uryga, A., et al. Inhibition of Kv1.3 channels in human jurkat T cells by xanthohumol and isoxanthohumol. J. Membr. Biol. 248(4), 705-711 (2015).

    4. Quifer-Rada, P., Martínez-Huélamo, M., Chiva-Blanch, G., et al. Urinary isoxanthohumol is a specific and accurate biomarker of beer consumption. J. Nutr. 144(4), 484-488 (2014).