A potent CYP3A4 inhibitor
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6,7-dihydroxy Bergamottin

Item No. 10009598

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-[[(2E)-6,7-dihydroxy-3,7-dimethyl-2-octenyl]oxy]-7H-fuoro[3,2-g][1]benzopyran-7-one
CAS Number
145414-76-2
Synonyms
  • 6,7-DHB
Molecular Formula
C21H24O6
Formula Weight
372.4
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlDMSO:PBS (pH 7.2) (1:1): 0.5 mg/mlEthanol: 10 mg/ml
λmax
221, 250, 309 nm
SMILES
O=C1C=CC2=C(OC/C=C(C)/CCC(O)C(C)(O)C)C3=C(OC=C3)C=C2O1
InChi Code
InChI=1S/C21H24O6/c1-13(4-6-18(22)21(2,3)24)8-10-26-20-14-5-7-19(23)27-17(14)12-16-15(20)9-11-25-16/h5,7-9,11-12,18,22,24H,4,6,10H2,1-3H3/b13-8+
InChi Key
IXZUPBUEKFXTSD-MDWZMJQESA-N
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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    5 mg

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    10 mg

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    25 mg

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    Product Description

    6,7-dihydroxy Bergamottin (6,7-DHB) is a potent inhibitor of CYP3A4 (IC50 = 25 µM).1 It appears to be the primary compound in grapefruit juice that is responsible for inhibition of testosterone 6β-hydrolase activity. Ingestion of grapefruit juice during treatment regimes with drugs normally metabolized by cytochrome P450 enzymes of the CYP3A subfamily results in a substantial increase in plasma concentration of these agents.2,1 However, giving a patient grapefruit juice or just 6,7-DHB could be advantageous in cases where a drug is metabolized too quickly by CYP3A4.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Edwards, D.J., Bellevue, F.H., III, and Woster, P.M. Identification of 6',7'-dihydroxybergamottin, a cytochrome P450 inhibitor, in grapefruit juice. Drug Metab. Dispos. 24(12), 1287-1290 (1996).

    2. Bellevue, F.H., III, Woster, P.M., Edwards, D.J., et al. Synthesis and biological evalution of 6',7'-dihydroxybergamottin (6,7-DHB), a naturally occurring inhibitor of cytochrome P450 3A4. Bioorg. Med. Chem. Lett. 7(20), 2593-2598 (1997).