A potent CYP3A4 inhibitor from grapefruit
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Isomer(s)
39268Notopterol
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6’,7’-Epoxybergamottin

Item No. 19760

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-[[(2E)-5-(3,3-dimethyl-2-oxiranyl)-3-methyl-2-penten-1-yl]oxy]-7H-furo[3,2-g][1]benzopyran-7-one
CAS Number
206978-14-5
Synonyms
  • Epoxybergamottin
Molecular Formula
C21H22O5
Formula Weight
354.4
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlDMSO:PBS (pH 7.2) (1:1): 0.50 mg/mlEthanol: 10 mg/ml
λmax
251, 311 nm
SMILES
O=C1C=CC2=C(OC/C=C(C)/CCC3C(C)(C)O3)C4=C(OC=C4)C=C2O1
InChi Code
InChI=1S/C21H22O5/c1-13(4-6-18-21(2,3)26-18)8-10-24-20-14-5-7-19(22)25-17(14)12-16-15(20)9-11-23-16/h5,7-9,11-12,18H,4,6,10H2,1-3H3/b13-8+
InChi Key
OOKSPQLCQUBEKU-MDWZMJQESA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
Certificates of Analysis & Batch Specific Data

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    1 mg

    $51

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    5 mg

    $191

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    10 mg

    $355

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    25 mg

    $758

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    Product Description

    6'7'-Epoxybergamottin is a furanocoumarin found in grapefruit.1 It is a potent inhibitor of the cytochrome P450 (CYP) isoform CYP3A4 with an IC50 value of 0.30 ppm in a cell-free assay, 0.33 µM in HL7 human liver cells, and 0.22 µM in S9 human intestine cells.2 It has been studied in the context of drug interactions with grapefruit constituents. It is found in grapefruit juice at concentrations of 0.1-7.4 µM and inhibits the transport of talinolol (Item No. 16116), a permeability glycoprotein (P-gp/ABCB1) transporter substrate, across Caco-2 cell monolayers (IC50 = 0.7 µM).3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Manthey, J.A., Myung, K., Mertens-Talcott, S., et al. The isolation of minor-occurring furano coumarins in grapefruit and analysis of their inhibition of CUP 2A4 and P-Glycoprotein transport of talinolol from caco-2 cells. Proc. Fla. State Hort. Soc. 119, 361-366 (2006).

    2. Row, E.C., Brown, S.A., Stachulski, A.V., et al. Design, synthesis and evaluation of furanocoumarin monomers as inhibitors of CYP3A4. Org. Biomol. Chem. 4(8), 1604-1610 (2006).

    3. de Castro, W.V., Mertens-Talcott, S., Derendorf, H., et al. Grapefruit juice-drug interactions: Grapefruit juice and its components inhibit P-glycoprotein (ABCB1) mediated transport of talinolol in Caco-2 cells. J. Pharm. Sci. 96(10), 2808-2817 (2007).