A flavonoid with diverse biological activities
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(±)-6-Prenylnaringenin

Item No. 34499

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-6-(3-methyl-2-buten-1-yl)-4H-1-benzopyran-4-one
CAS Number
68682-01-9
Synonyms
  • (±)-6-PN
Molecular Formula
C20H20O5
Formula Weight
340.4
Purity
≥95%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
Methanol: soluble
SMILES
O=C1C2=C(C(C/C=C(C)\C)=C(C=C2OC(C1)C3=CC=C(C=C3)O)O)O
InChi Code
InChI=1S/C20H20O5/c1-11(2)3-8-14-15(22)9-18-19(20(14)24)16(23)10-17(25-18)12-4-6-13(21)7-5-12/h3-7,9,17,21-22,24H,8,10H2,1-2H3
InChi Key
YHWNASRGLKJRJJ-UHFFFAOYSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Product Description

    (±)-6-Prenylnaringenin ((±)-6-PN) is a flavonoid that has been found in the hop plant, H. lupulus, and has diverse biological activities.1,2 It inhibits the T-type voltage-gated calcium (Cav) channel Cav3.2 and high-voltage-activated calcium currents in whole-cell patch-clamp assays using HEK293 cells (IC50s = 0.912 and 4.765 µM, respectively).1 It inhibits proliferation of PC3 and DU145 prostate cancer cells (IC50s = 18.4 and 29.1 µM, respectively).2 (±)-6-PN (20 and 30 mg/kg) reduces mechanical allodynia in a mouse model of neuropathic pain induced by partial sciatic nerve ligation.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Sekiguchi, F., Fujita, T., Deguchi, T., et al. Blockade of T-type calcium channels by 6-prenylnaringenin, a hop component, alleviates neuropathic and visceral pain in mice. Neuropharmacology 138, 232-244 (2018).

    2. Delmulle, L., Bellahcène, A., Dhooge, W., et al. Anti-proliferative properties of prenylated flavonoids from hops (Humulus lupulus L.) in human prostate cancer cell lines. Phytomedicine 13(9-10), 732-734 (2006).