Dihydrowogonin

Base Information

• Chemical Name: Dihydrowogonin
• CAS No.: 4431-41-8
• Molecular Formula: C16H14O5
• Molecular Weight: 286.284
• Metabolomics Workbench ID: 27812
• Wikidata: Q104375668
• Mol file: 4431-41-8.mol

Synonyms:Dihydrowogonin;5,7-dihydroxy-8-methoxy-2-phenyl-2,3-dihydrochromen-4-one;4431-41-8;SCHEMBL9063227;5,7-Dihydroxy-8-methoxyflavanone;CHEBI:174734;LMPK12140661

Chemical Property of Dihydrowogonin

Chemical Property:

• XLogP3: 2.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 286.08412354
• Heavy Atom Count: 21
• Complexity: 379

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C(C2=C1OC(CC2=O)C3=CC=CC=C3)O)O

Technology Process of Dihydrowogonin

There total 9 articles about Dihydrowogonin 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: 61.0%

6′-hydroxy-2′,3′,4′-trimethoxychalcone (70185-52-3,74064-14-5) → rac-2,3-dihydrooroxylin A (18956-18-8) + 5,7-dihydroxy-8-methoxyflavanone (4431-41-8)

Guidance literature:

With hydrogen bromide; In acetic acid; for 2h; Reflux;

DOI:10.1016/j.tetlet.2016.02.093

Reference yield:

3,4,5-trimethoxyphenol (642-71-7) → rac-2,3-dihydrooroxylin A (18956-18-8) + 5,7-dihydroxy-8-methoxyflavanone (4431-41-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 0.5 h / Reflux

2: sodium hydrogencarbonate / ethyl acetate / 0.5 h / 20 °C

3: hydrogen bromide / acetic acid / 2 h / Reflux

With hydrogen bromide; sodium hydrogencarbonate; In acetic acid; ethyl acetate;

DOI:10.1016/j.tetlet.2016.02.093

Reference yield:

Cinnamoyl chloride (102-92-1,17082-09-6) → rac-2,3-dihydrooroxylin A (18956-18-8) + 5,7-dihydroxy-8-methoxyflavanone (4431-41-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 0.5 h / Reflux

2: sodium hydrogencarbonate / ethyl acetate / 0.5 h / 20 °C

3: hydrogen bromide / acetic acid / 2 h / Reflux

With hydrogen bromide; sodium hydrogencarbonate; In acetic acid; ethyl acetate;

DOI:10.1016/j.tetlet.2016.02.093

upstream raw materials:

Iretol

Cinnamoyl chloride

rac-2,3-dihydrooroxylin A

6′-hydroxy-2′,3′,4′-trimethoxychalcone

Downstream raw materials:

(2S)-5-hydroxy-7,8-dimethoxyflavanone

rac-2,3-dihydrooroxylin A

5?hydroxy?7,8?dimethoxyflavanone

dihydrobaicalein

Refernces