6',7'-Dihydroxybergamottin

Base Information

• Chemical Name: 6',7'-Dihydroxybergamottin
• CAS No.: 145414-76-2
• Molecular Formula: C₂₁H₂₄O₆
• Molecular Weight: 372.418
• DSSTox Substance ID: DTXSID001045401
• Nikkaji Number: J687.532G,J784.174D
• Wikipedia: 6%27,7%27-Dihydroxybergamottin,6',7'-Dihydroxybergamottin
• Wikidata: Q3599478
• ChEMBL ID: CHEMBL513494
• Mol file: 145414-76-2.mol

Synonyms:6',7'-dihydroxybergamottin;6,7-DHB

Chemical Property of 6',7'-Dihydroxybergamottin

Chemical Property:

• Melting Point: 112-113 °C
• Boiling Point: 578.2 °C at 760 mmHg
• PKA: 14.65±0.29(Predicted)
• Flash Point: 303.5 °C
• PSA: 93.04000
• Density: 1.26 g/cm³
• LogP: 5.02190
• Storage Temp.: 2-8°C
• Solubility.: ethanol: soluble
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 372.15728848
• Heavy Atom Count: 27
• Complexity: 596

Purity/Quality:

98%,99%, ^*data from raw suppliers

6'',7''-DihydroxyBergamottin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCOC1=C2C=CC(=O)OC2=CC3=C1C=CO3)CCC(C(C)(C)O)O
• Isomeric SMILES: C/C(=C\COC1=C2C=CC(=O)OC2=CC3=C1C=CO3)/CCC(C(C)(C)O)O
• 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. A minor metabolite of Bergamottin (B318400). Metabolization of Bergamottin by cytochromes P 450 2B6 and 3A5. 6′,7′-dihydroxybergamottin has been used to study its effect on the inhibition of cytochrome P450 (CYP)-mediated triazolam hydroxylation in dog liver microsomes.

Technology Process of 6',7'-Dihydroxybergamottin

There total 5 articles about 6',7'-Dihydroxybergamottin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 74.0%

Epoxybergamottin (206978-14-5) → 6',7'-dihydroxybergamottin (145414-76-2)

Guidance literature:

With perchloric acid; In tetrahydrofuran; water; at 20 ℃; for 0.5h;

Reference yield:

bergamottin (7380-40-7) → 6',7'-dihydroxybergamottin (145414-76-2)

Guidance literature:

With methanesulfonamide; potassium carbonate; potassium hexacyanoferrate(III); osmium(VIII) oxide; (DHQ)2-PHAL; In water; tert-butyl alcohol; at 7 ℃; for 21.5h;

DOI:10.1016/S0040-4020(02)00739-1

Reference yield:

trans-geranyl bromide (6138-90-5) → 6',7'-dihydroxybergamottin (145414-76-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 70 percent / K₂CO₃ / acetone / 1 h / Heating

2: 81 percent / 3-chloroperoxybenzoic acid / CH₂Cl₂ / 2.5 h / -10 °C

3: 68 percent / aq. perchloric acid / dioxane / 1 h / 20 °C

With perchloric acid; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; In 1,4-dioxane; dichloromethane; acetone;

DOI:10.1039/b601096b

upstream raw materials:

Epoxybergamottin

bergamottin

trans-geranyl bromide

bergaptol

Downstream raw materials:

Epoxybergamottin

Refernces

• 1、 Bellevue III, Frank H.,Woster, Patrick M.,Edwards, David J.,He, Kan,Hollenberg, Paul F.. "Synthesis and biological evaluation of 6',7'-dihydroxybergamottin (6,7-DHB, a naturally occurring inhibitor of cytochrome P450 3A4". . p. 2593 - 2598. Retrieved 1997.
• 2、 -. "SYNTHESIS OF SPIRO ORTHO ESTERS, SPIRO ORTHO CARBONATES, AND INTERMEDIATES". Page 30. . Retrieved 2008/06/13.