Prunetin

Base Information

• Chemical Name: Prunetin
• CAS No.: 552-59-0
• Molecular Formula: C16H12O5
• Molecular Weight: 284.268
• Hs Code.: 2914509090
• Mol file: 552-59-0.mol

Synonyms:Isoflavone,4',5-dihydroxy-7-methoxy- (7CI,8CI);Prunetin (6CI);5,4'-Dihydroxy-7-methoxyisoflavone;Prunetin;5-Hydroxy-3-(4-hydroxyphenyl)-7-methoxy-4H-chromen-4-one;5-Hydroxy-3-(4-hydroxyphenyl)-7-methoxy-4-benzopyrone;

Chemical Property of Prunetin

Chemical Property:

• Appearance/Colour: Creamy white crystalline powder.
• Vapor Pressure: 1.49E-12mmHg at 25°C
• Melting Point: 240-242 °C
• Refractive Index: 1.668
• Boiling Point: 546.5 °C at 760 mmHg
• PKA: 6.35±0.20(Predicted)
• Flash Point: 209.7 °C
• PSA: 79.90000
• Density: 1.42g/cm³
• LogP: 2.87980
• Storage Temp.: Inert atmosphere,Room Temperature

Purity/Quality:

≥98% ^*data from raw suppliers

Prunetin ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Uses: Prunetin is isoflavone with diverse biological activities. Prunetin is an antagonist of the progesterone receptor when used at concentrations of 25 and 50 μM.

Technology Process of Prunetin

There total 22 articles about Prunetin 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: 78.0%

5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on (446-72-0) + methyl iodide (74-88-4) → prunetin (552-59-0)

Guidance literature:

With potassium carbonate; In acetone; at 50 ℃; for 1h; sonication;

DOI:10.1016/j.bmc.2005.04.082

Reference yield: 72.0%

3-(4-hydroxyphenyl)-5,7-dimethoxychromen-4-one (69127-80-6) → prunetin (552-59-0)

Guidance literature:

With aluminium trichloride; In nitrobenzene; for 2.5h; Ambient temperature;

Reference yield:

5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on (446-72-0) + S-adenosyl-L-methionine (485-80-3,15519-60-5,60018-85-1,60018-86-2,79845-28-6) → 5,7-Dihydroxy-3-(4-methoxy-phenyl)-chromen-4-on (491-80-5) + prunetin (552-59-0)

Guidance literature:

With sodium azide; T₁₃₃M and Y₃₂₆H mutant of isoeugenol phenylpropanoid O-methyltransferase from Clarkia breweri; In aq. buffer; at 30 ℃; for 48h; pH=7.5; Reagent/catalyst; regioselective reaction; Enzymatic reaction;

DOI:10.1002/cctc.202000471

upstream raw materials:

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

dimethyl sulfate

4',5,7-trimethoxyisoflavone

5-hydroxy-3-(4-hydroxy-phenyl)-7-methoxy-4-oxo-4H-chromene-2-carboxylic acid

Downstream raw materials:

2-(2,6-dihydroxy-4-methoxyphenyl)-3-(4-hydroxyphenyl)-pyrimido[1,2-a]benzimidazole

4-hydroxyphenylacetate

5,4'-diacetoxy-7-methoxyisoflavone

2,6,4'-trihydroxy-4-methoxy-deoxybenzoin

Refernces

• 1、 Tang, Qingyun,Vianney, Yoanes M.,Weisz, Klaus,Grathwol, Christoph W.,Link, Andreas,Bornscheuer, Uwe T.,Pavlidis, Ioannis V.. "Influence of Substrate Binding Residues on the Substrate Scope and Regioselectivity of a Plant O-Methyltransferase against Flavonoids". . p. 3721 - 3727. Retrieved 2020/06/02.
• 2、 Zheng, Xing,Yao, Xu,Liu, Yunmei,Zheng, Zitong,Cao, Jianguo,Liao, Duanfang. "Synthesis and cytotoxic activity of genistein derivatives". experimental part. p. 1296 - 1306. Retrieved 2011/10/12.