8-Hydroxygenistein

Base Information

• Chemical Name: 8-Hydroxygenistein
• CAS No.: 13539-27-0
• Molecular Formula: C15H10O6
• Molecular Weight: 286.241
• DSSTox Substance ID: DTXSID40159329
• Nikkaji Number: J952.352I
• Wikidata: Q83027634
• Mol file: 13539-27-0.mol

Synonyms:8-Hydroxygenistein;13539-27-0;BRN 1294503;5,7,8-trihydroxy-3-(4-hydroxyphenyl)chromen-4-one;Isoflavone, 4',5,7,8-tetrahydroxy-;3-(4-Hydroxyphenyl)-5,7,8-trihydroxy-4H-1-benzopyran-4-one;5,7,8-Trihydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one;4H-1-Benzopyran-4-one, 3-(4-hydroxyphenyl)-5,7,8-trihydroxy-;4',5,7,8-Tetrahydroxyisoflavone;SCHEMBL572094;DTXSID40159329;LS-39729

Chemical Property of 8-Hydroxygenistein

Chemical Property:

• Vapor Pressure: 1.24E-14mmHg at 25°C
• Melting Point: 330 °C(Solv: water (7732-18-5); ethanol (64-17-5))
• Refractive Index: 1.767
• Boiling Point: 592.467 °C at 760 mmHg
• PKA: 6.65±0.20(Predicted)
• Flash Point: 230.247 °C
• PSA: 111.13000
• Density: 1.655 g/cm³
• LogP: 2.28240
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 286.04773803
• Heavy Atom Count: 21
• Complexity: 439

Purity/Quality:

99% ^*data from raw suppliers

8-Hydroxygenistein ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C2=COC3=C(C2=O)C(=CC(=C3O)O)O)O
• Uses: 8-?Hydroxygenistein is an orthohydroxygenisteins, a derivative of genistein. 8-Hydroxygenistein is an excellent antioxidant agent and may be effective in preventing damage induced by free radical.

Technology Process of 8-Hydroxygenistein

There total 4 articles about 8-Hydroxygenistein 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:

7-((2S)-tetrahydro-3,4,5-trihydroxy-6-(hydroxymethyl)-2H-pyran-2-yloxy)-5,8-dihydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one → 8-Hydroxygenistein (13539-27-0)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogenchloride / methanol; water / Reflux

2: hydrogen bromide

With hydrogenchloride; hydrogen bromide; In methanol; water;

DOI:10.1016/j.phytochem.2017.01.002

Reference yield:

5,7,8-trihydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one → 8-Hydroxygenistein (13539-27-0)

Guidance literature:

With hydrogen bromide;

DOI:10.1016/j.phytochem.2017.01.002

Reference yield:

5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on (446-72-0) → 8-Hydroxygenistein (13539-27-0) + 6-Hydroxygenistein (13539-26-9)

Guidance literature:

With Micrococcus or Arthrobacter; for 48h; Yield given. Yields of byproduct given;

DOI:10.1016/S0031-9422(98)80069-1

upstream raw materials:

5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on

Refernces

• 1、 Klus, Klaus,Barz, Wolfgang. "Formation of polyhydroxylated isoflavones from the isoflavones genistein and biochanin a by bacteria isolated from tempe". . p. 1045 - 1048. Retrieved 2007/10/03.