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| | 6',7'-DIHYDROXYBERGAMOTTIN Basic information |
| Product Name: | 6',7'-DIHYDROXYBERGAMOTTIN | | Synonyms: | 4-[[(2E)-6,7-Dihydroxy-3,7-dimethyl-2-octen-1-yl]oxy]-7H-furo[3,2-g][1]benzopyran-7-one;6',7'-DIHYDROXYBERGAMOTTIN;6,7-dihydroxybergaMottin(DHB);7H-Furo[3,2-g][1]benzopyran-7-one, 4-[[(2E)-6,7-dihydroxy-3,7-dimethyl-2-octen-1-yl]oxy]- | | CAS: | 145414-76-2 | | MF: | C21H24O6 | | MW: | 372.41 | | EINECS: | | | Product Categories: | Heterocycles;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Drug and Xenobiotic Metabolism;Multi-Drug Resistance and Drug Metabolism;Substrates, Inducers, Inhibitors | | Mol File: | 145414-76-2.mol |  |
| | 6',7'-DIHYDROXYBERGAMOTTIN Chemical Properties |
| 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 | | 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+ | | InChIKey | IXZUPBUEKFXTSD-MDWZMJQESA-N | | SMILES | C\C(CCC(O)C(C)(C)O)=C/COc1c2C=CC(=O)Oc2cc3occc13 |
| WGK Germany | 3 | | Storage Class | 11 - Combustible Solids |
| | 6',7'-DIHYDROXYBERGAMOTTIN Usage And Synthesis |
| 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 | A minor metabolite of Bergamottin. Metabolization of Bergamottin by cytochromes P 450 2B6 and 3A5. | | Uses | A minor metabolite of Bergamottin (B318400). Metabolization of Bergamottin by cytochromes P 450 2B6 and 3A5. | | 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. | | 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 | | 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. |
| | 6',7'-DIHYDROXYBERGAMOTTIN Preparation Products And Raw materials |
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