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6′,7′-dihydroxy Bergamottin (CAS 145414-76-2)

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Alternate Names:
6,7-DHB; 4-[[(2E)-6,7-dihydroxy-3,7-dimethyl-2-octenyl]oxy]-7H-fuoro[3,2-g][1]benzopyran-7-one
Application:
6′,7′-dihydroxy Bergamottin is a potent CYP3A4 inhibitor
CAS Number:
145414-76-2
Purity:
>98%
Molecular Weight:
372.42
Molecular Formula:
C21H24O6
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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6′,7′-dihydroxy Bergamottin is a compound of interest in the field of food chemistry, specifically in understanding the flavors and aromas of citrus fruits. It is investigated for its role in the characteristic taste profile of grapefruit and related citrus varieties. In biochemical research, it serves as a model compound for studying the interaction between dietary components and enzymes involved in metabolism, such as cytochrome P450s. The compound′s ability to modulate enzyme activity is a key focus in these studies, which can provide valuable information for understanding the influence of diet on chemical metabolism. Additionally, 6′,7′-dihydroxy Bergamottin is used in the synthesis of flavor compounds and in the study of photochemistry related to furanocoumarins, examining how light affects its stability and reactivity. The compound is also a reference material in the analysis of citrus product composition and quality control.


6′,7′-dihydroxy Bergamottin (CAS 145414-76-2) References

  1. 6',7'-Dihydroxybergamottin in grapefruit juice and Seville orange juice: effects on cyclosporine disposition, enterocyte CYP3A4, and P-glycoprotein.  |  Edwards, DJ., et al. 1999. Clin Pharmacol Ther. 65: 237-44. PMID: 10096255
  2. Grapefruit-felodipine interaction: effect of unprocessed fruit and probable active ingredients.  |  Bailey, DG., et al. 2000. Clin Pharmacol Ther. 68: 468-77. PMID: 11103749
  3. Seville orange juice-felodipine interaction: comparison with dilute grapefruit juice and involvement of furocoumarins.  |  Malhotra, S., et al. 2001. Clin Pharmacol Ther. 69: 14-23. PMID: 11180034
  4. Time course of recovery of cytochrome p450 3A function after single doses of grapefruit juice.  |  Greenblatt, DJ., et al. 2003. Clin Pharmacol Ther. 74: 121-9. PMID: 12891222
  5. The effects of fruit juices on drug disposition: a new model for drug interactions.  |  Dresser, GK. and Bailey, DG. 2003. Eur J Clin Invest. 33 Suppl 2: 10-6. PMID: 14641551
  6. 6'7'-Dihydroxybergamottin contributes to the grapefruit juice effect.  |  Kakar, SM., et al. 2004. Clin Pharmacol Ther. 75: 569-79. PMID: 15179411
  7. Bergamottin contribution to the grapefruit juice-felodipine interaction and disposition in humans.  |  Goosen, TC., et al. 2004. Clin Pharmacol Ther. 76: 607-17. PMID: 15592332
  8. Grapefruit juice-drug interactions: Grapefruit juice and its components inhibit P-glycoprotein (ABCB1) mediated transport of talinolol in Caco-2 cells.  |  de Castro, WV., et al. 2007. J Pharm Sci. 96: 2808-17. PMID: 17542018
  9. Biotransformations of 6',7'-dihydroxybergamottin and 6',7'-epoxybergamottin by the citrus-pathogenic fungi diminish cytochrome P450 3A4 inhibitory activity.  |  Myung, K., et al. 2012. Bioorg Med Chem Lett. 22: 2279-82. PMID: 22342630
  10. Inhibition of CYP3A4 by 6',7'-dihydroxybergamottin in human CYP3A4 over-expressed hepG2 cells.  |  Araki, N., et al. 2012. J Pharm Pharmacol. 64: 1715-21. PMID: 23146034
  11. Structural Insights into the Interaction of Cytochrome P450 3A4 with Suicide Substrates: Mibefradil, Azamulin and 6',7'-Dihydroxybergamottin.  |  Sevrioukova, IF. 2019. Int J Mol Sci. 20: PMID: 31480231
  12. Identification of 6',7'-dihydroxybergamottin, a cytochrome P450 inhibitor, in grapefruit juice.  |  Edwards, DJ., et al. 1996. Drug Metab Dispos. 24: 1287-90. PMID: 8971132
  13. Mechanisms of enhanced oral availability of CYP3A4 substrates by grapefruit constituents. Decreased enterocyte CYP3A4 concentration and mechanism-based inactivation by furanocoumarins.  |  Schmiedlin-Ren, P., et al. 1997. Drug Metab Dispos. 25: 1228-33. PMID: 9351897
  14. Grapefruit juice-felodipine interaction: effect of naringin and 6',7'-dihydroxybergamottin in humans.  |  Bailey, DG., et al. 1998. Clin Pharmacol Ther. 64: 248-56. PMID: 9757148

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

6′,7′-dihydroxy Bergamottin, 1 mg

sc-205162
1 mg
$104.00

6′,7′-dihydroxy Bergamottin, 10 mg

sc-205162A
10 mg
$624.00