6’,7’-Dihydroxy Bergamottin

• CAT Number: R010571
• CAS Number: 145414-76-2
• Molecular Formula: C21H24O6
• Molecular Weight: 372.417
• Purity: ≥95%
• Synonyms: 6,7-DHB; 4-[[(2E)-6,7-Dihydroxy-3,7-dimethyl-2-octen-1-yl]oxy]-7H-furo[3,2-g][1]benzopyran-7-one
• Target: Cytochrome P450
• Solubility: Soluble in DMSO
• Storage: Store at -20°C
• IUPAC Name: 4-[(E)-6,7-dihydroxy-3,7-dimethyloct-2-enoxy]furo[3,2-g]chromen-7-one
• InChI: 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: CC(=CCOC1=C2C=CC(=O)OC2=CC3=C1C=CO3)CCC(C(C)(C)O)O

6’,7’-Dihydroxy Bergamottin (Cat.No:R010571) is a natural furanocoumarin compound found in grapefruit. It exhibits inhibitory effects on the enzyme cytochrome P450 3A4 (CYP3A4), which metabolizes various drugs. This interaction can impact drug metabolism, leading to altered drug levels in the body. It’s of interest in drug interaction studies.

Reference

1: Araki N, Tsuruoka S, Hasegawa G, Yanagihara H, Omasa T, Enosawa S, Yamazoe Y,
Fujimura A. Inhibition of CYP3A4 by 6/’,7/’-dihydroxybergamottin in human CYP3A4
over-expressed hepG2 cells. J Pharm Pharmacol. 2012 Dec;64(12):1715-21. doi:
10.1111/j.2042-7158.2012.01562.x. Epub 2012 Aug 2. PubMed PMID: 23146034.

2: Myung K, Manthey JA, Narciso JA. Biotransformations of
6/’,7/’-dihydroxybergamottin and 6/’,7/’-epoxybergamottin by the citrus-pathogenic
fungi diminish cytochrome P450 3A4 inhibitory activity. Bioorg Med Chem Lett.
2012 Mar 15;22(6):2279-82. doi: 10.1016/j.bmcl.2012.01.081. Epub 2012 Jan 30.
PubMed PMID: 22342630.

3: Ishihara M, Toda H, Sunagane N, Ohta T. [Furanocoumarins contents and
cytochrome P450 3A (CYP3A) inhibitory activities of various processed fruit peel
products: outflow of 6/’,7/’-Dihydroxybergamottin during processing treatment of
peel]. Yakugaku Zasshi. 2011;131(5):679-84. Japanese. PubMed PMID: 21532264.

4: Edwards DJ, Fitzsimmons ME, Schuetz EG, Yasuda K, Ducharme MP, Warbasse LH,
Woster PM, Schuetz JD, Watkins P. 6/’,7/’-Dihydroxybergamottin in grapefruit juice
and Seville orange juice: effects on cyclosporine disposition, enterocyte CYP3A4,
and P-glycoprotein. Clin Pharmacol Ther. 1999 Mar;65(3):237-44. PubMed PMID:
10096255.

5: Bailey DG, Kreeft JH, Munoz C, Freeman DJ, Bend JR. Grapefruit
juice-felodipine interaction: effect of naringin and 6/’,7/’-dihydroxybergamottin
in humans. Clin Pharmacol Ther. 1998 Sep;64(3):248-56. PubMed PMID: 9757148.

6: Edwards DJ, Bellevue FH 3rd, Woster PM. Identification of
6/’,7/’-dihydroxybergamottin, a cytochrome P450 inhibitor, in grapefruit juice.
Drug Metab Dispos. 1996 Dec;24(12):1287-90. PubMed PMID: 8971132.