ChemicalBook > CAS DataBase List > 6',7'-DIHYDROXYBERGAMOTTIN

6',7'-DIHYDROXYBERGAMOTTIN

Product Name
6',7'-DIHYDROXYBERGAMOTTIN
CAS No.
145414-76-2
Chemical Name
6',7'-DIHYDROXYBERGAMOTTIN
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]-
CBNumber
CB0765541
Molecular Formula
C21H24O6
Formula Weight
372.41
MOL File
145414-76-2.mol
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6',7'-DIHYDROXYBERGAMOTTIN Property

Melting point:
112-113 °C
Boiling point:
578.2±50.0 °C(Predicted)
Density 
1.260
storage temp. 
2-8°C
solubility 
ethanol: soluble
pka
14.65±0.29(Predicted)
form 
Solid
color 
white to off-white
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Safety

WGK Germany 
3
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
UC441
Product name
6,-7-Dihydroxybergamottin
Packaging
5mg
Price
$896
Updated
2024/03/01
Sigma-Aldrich
Product number
UC441
Product name
6,-7-Dihydroxybergamottin
Packaging
10mg
Price
$1520
Updated
2022/05/15
Cayman Chemical
Product number
10009598
Product name
6,7-dihydroxy Bergamottin
Purity
≥98%
Packaging
1mg
Price
$20
Updated
2024/03/01
Cayman Chemical
Product number
10009598
Product name
6,7-dihydroxy Bergamottin
Purity
≥98%
Packaging
5mg
Price
$85
Updated
2024/03/01
Cayman Chemical
Product number
10009598
Product name
6,7-dihydroxy Bergamottin
Purity
≥98%
Packaging
10mg
Price
$146
Updated
2024/03/01
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6',7'-DIHYDROXYBERGAMOTTIN Chemical Properties,Usage,Production

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. 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.

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

Raw materials

Preparation Products

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6',7'-DIHYDROXYBERGAMOTTIN Suppliers

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View Lastest Price from 6',7'-DIHYDROXYBERGAMOTTIN manufacturers

Career Henan Chemical Co
Product
6',7'-DIHYDROXYBERGAMOTTIN 145414-76-2
Price
US $1.00/KG
Min. Order
1KG
Purity
99.0%
Supply Ability
100kg
Release date
2020-01-14

145414-76-2, 6',7'-DIHYDROXYBERGAMOTTINRelated Search:

4-ALLYLOXYCOUMARIN 6',7'-DIHYDROXYBERGAMOTTIN 4-ETHOXYCOUMARIN 1-BENZOFURAN-5-YLMETHANOL

  • 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]-
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