4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-8-(3-methyl-2-butenyl)-2-phenyl-

Base Information

• Chemical Name: 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-8-(3-methyl-2-butenyl)-2-phenyl-
• CAS No.: 72247-82-6
• Molecular Formula: C20H20O4
• Molecular Weight: 324.376
• Mol file: 72247-82-6.mol

Synonyms:5,7-dihydroxy-8-C-prenylflavanone;5,7-Dihydroxy-8-(3-methyl-but-2-enyl)-2-phenyl-chroman-4-one;Glabranin;

Chemical Property of 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-8-(3-methyl-2-butenyl)-2-phenyl-

Chemical Property:

• Melting Point: 147-148 °C
• Boiling Point: 545.9±50.0 °C(Predicted)
• PSA: 66.76000
• Density: 1.244±0.06 g/cm3(Predicted)
• LogP: 4.31300

Purity/Quality:

8-Prenyl-rac-pinocembrin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 8-Prenyl-rac-pinocembrin is a natural product found in the bark of Lonchocarpus haberi from Monteverde, Costa Rica.

Technology Process of 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-8-(3-methyl-2-butenyl)-2-phenyl-

There total 9 articles about 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-8-(3-methyl-2-butenyl)-2-phenyl- 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: 65.0%

5,7-dimethoxymethoxy-8-(3,3-dimethylallyl)-flavanone (1075171-40-2) → 5,7-dihydroxy-8-C-prenylflavanone (72247-82-6)

Guidance literature:

With hydrogenchloride; water; In methanol; for 0.75h; Reflux;

DOI:10.1016/j.bmc.2008.07.031

Reference yield: 62.9%

(E)-3-phenyl-1-(2,4,6-trihydroxy-3-(3-methylbut-2-enyl)phenyl)prop-2-en-1-one (72247-78-0) → 5,7-dihydroxy-8-C-prenylflavanone (72247-82-6)

Guidance literature:

With sodium acetate; In ethanol; at 20 ℃; for 72h;

Reference yield: 8.0%

pinocembrin (480-39-7,61490-55-9,68745-38-0) + prenyl bromide (870-63-3) → 5,7-dihydroxy-8-C-prenylflavanone (72247-82-6) + 5-hydroxyl-7-prenyloxy-2,3-dihydroflavanone (59718-55-7,94393-10-9) + 5,7-dihydroxy-6-(3-methylbut-2-enyl)-2-phenylchroman-4-one (72018-32-7) + 6-C,7-O-diprenylpinocembrin

Guidance literature:

With potassium hydroxide; 18-crown-6 ether; In methanol; for 28h; Further byproducts given; Ambient temperature;

DOI:10.3987/com-96-7415

upstream raw materials:

pinocembrin

prenyl bromide

dimethylallyl diphosphate

(E)-3-phenyl-1-(2,4,6-trihydroxy-3-(3-methylbut-2-enyl)phenyl)prop-2-en-1-one

Downstream raw materials:

5-hydroxy-7-methoxy-3-C-prenylflavone