| Identification | Back Directory | [Name]
6',7'-DIHYDROXYBERGAMOTTIN | [CAS]
145414-76-2 | [Synonyms]
6',7'-DIHYDROXYBERGAMOTTIN
6,7-dihydroxybergaMottin(DHB)
4-[[(2E)-6,7-Dihydroxy-3,7-dimethyl-2-octen-1-yl]oxy]-7H-furo[3,2-g][1]benzopyran-7-one
7H-Furo[3,2-g][1]benzopyran-7-one, 4-[[(2E)-6,7-dihydroxy-3,7-dimethyl-2-octen-1-yl]oxy]- | [Molecular Formula]
C21H24O6 | [MDL Number]
MFCD01311879 | [MOL File]
145414-76-2.mol | [Molecular Weight]
372.41 |
| Chemical Properties | Back Directory | [Melting point ]
112-113 °C | [Boiling point ]
578.2±50.0 °C(Predicted) | [density ]
1.260 | [storage temp. ]
2-8°C | [solubility ]
ethanol: soluble | [form ]
Solid | [pka]
14.65±0.29(Predicted) | [color ]
white to off-white |
| Hazard Information | Back Directory | [Description]
6,7-dihydroxy Bergamottin (6,7-DHB) is a potent inhibitor of CYP3A4 (IC50 = 25 μM). 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. 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. | [Uses]
6′,7′-dihydroxybergamottin has been used to study its effect on the inhibition of cytochrome P450 (CYP)-mediated triazolam hydroxylation in dog liver microsomes. | [Uses]
A minor metabolite of Bergamottin (B318400). Metabolization of Bergamottin by cytochromes P 450 2B6 and 3A5. | [Uses]
A minor metabolite of Bergamottin. Metabolization of Bergamottin by cytochromes P 450 2B6 and 3A5. | [Definition]
ChEBI: 6',7'-Dihydroxybergamottin is a member of psoralens. | [Biochem/physiol Actions]
CYP3A4 inhibitor. | [in vitro]
6,7-dhb significantly blocked the testosterone 6β-hydrolase in human liver microsomes and human cyp3a4 expressed in escherichia coli membrane in a time- and concentration-dependent manner. furthermore, 6,7-dhb proved to be a potent nadph- and time-dependent inhibitor of cyp3a4 [1]. 6,7-dhb concentration-dependently inhibited nifedipine (nfp) oxidation in hepg2-gs-3a4 cell, a cell line from hepatoblastoma with overexpression of human cyp3a4 [2]. | [in vivo]
male wistar-st rats were intraduodenally administered with 6,7-dhb at a dose of 3.4 mg/ml. after 4 hours, 6,7-dhb had no significant effects on the nfp plasma concentrations, suggesting that 6,7-dhb had no pharmacokinetic effect on the rats [3]. | [IC 50]
25 μm | [storage]
Store at -20°C | [References]
[1]. bellevue, f., woster, p., edwards, d., he, k., & hollenberg, p. synthesis and biological evaluation of 6′,7′-dihydroxybergamottin (6,7-dhb), a naturally occurring inhibitor of cytochrome p450 3a4. bioorganic & medicinal chemistry letters. 1997; 7(20): 2593-2598.
[2]. araki, n., tsuruoka, s., hasegawa, g., yanagihara, h., omasa, t., & enosawa, s. et al. inhibition of cyp3a4 by 6′,7′-dihydroxybergamottin in human cyp3a4 over-expressed hepg2 cells. journal of pharmacy and pharmacology. 2012; 64(12): 1715-1721.
[3]. mohri, k., & uesawa, y. effects of furanocoumarin derivatives in grapefruit juice on nifedipine pharmacokinetics in rats. pharmaceutical research, 2001;18(2):177-182. |
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