A prenylated furanocoumarin with diverse biological activities
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Isomer(s)
10009439Bergamottin
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8-Geranyloxypsoralen

Item No. 35167

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
9-[[(2E)-3,7-dimethyl-2,6-octadien-1-yl]oxy]-7H-furo[3,2-g][1]benzopyran-7-one
CAS Number
7437-55-0
Synonyms
  • 8-Geranopsoralen
  • 8-Geranoxypsoralen
  • Xanthotoxol geranyl ether
Molecular Formula
C21H22O4
Formula Weight
338.4
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Acetonitrile: SolubleChloroform: Soluble
λmax
219, 250, 302 nm
SMILES
C/C(C)=C/CC/C(C)=C/COC1=C(OC=C2)C2=CC(C=C3)=C1OC3=O
InChi Code
InChI=1S/C21H22O4/c1-14(2)5-4-6-15(3)9-11-24-21-19-17(10-12-23-19)13-16-7-8-18(22)25-20(16)21/h5,7-10,12-13H,4,6,11H2,1-3H3/b15-9+
InChi Key
SOVNCTNQAWWYAQ-OQLLNIDSSA-N
Origin
Plant/Heracleum hemsleyanum Diels
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

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    Product Description

    8-Geranyloxypsoralen is a prenylated furanocoumarin that has been found in C. limon and has diverse biological activities.1,2,3 It inhibits the cytochrome P450 (CYP) isoform CYP3A4 and β-secretase 1 (BACE1; IC50s = 3.93 and 20.4 µM, respectively).2,3 8-Geranyloxypsoralen (50 µM) inhibits Epstein-Barr virus activation induced by 12-O-tetradecanoylphorbol-13-acetate (TPA; Item No. 10008014) in infected Raji B-lymphoblastoid cells, TPA-induced superoxide generation in HL-60 leukemia cells, and LPS- and IFN-γ-induced nitric oxide (NO) generation in RAW 264.7 macrophages.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Miyake, Y., Murakami, A., Sugiyama, Y., et al. Identification of coumarins from lemon fruit citrus limon as inhibitors of in vitro tumor promotion and superoxide and nitric oxide generation. J. Agric. Food Chem. 47(8), 3151-3157 (1999).

    2. Row, E.C. Synthesis of 8-geranyloxypsoralen analogues and their evaluation as inhibitors of CYP3A4. Bioorg. Med. Chem. 14(11), 3865-3871 (2006).

    3. Marumoto, S., and Miyazawa, M. Structure-activity relationships for naturally occurring coumarins as β-secretase inhibitor. Bioorg. Med. Chem. 20(2), 784-788 (2012).