Fisetinidol

Base Information

• Chemical Name: Fisetinidol
• CAS No.: 490-49-3
• Molecular Formula: C₁₅H₁₄O₅
• Molecular Weight: 274.273
• DSSTox Substance ID: DTXSID401028831
• Nikkaji Number: J17.561G
• Wikipedia: Fisetinidol
• Wikidata: Q5454456
• Metabolomics Workbench ID: 21843
• ChEMBL ID: CHEMBL3039234
• Mol file: 490-49-3.mol

Synonyms:Fisetinidol;490-49-3;CHEBI:5066;3,7,3',4'-Tetrahydroxyflavan;(2R,3S)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,7-diol;Spectrum_001710;SpecPlus_000717;Spectrum2_000423;Spectrum3_000237;Spectrum4_001574;Spectrum5_000228;C09735;BSPBio_001913;KBioGR_002128;KBioSS_002190;SPECTRUM210014;DivK1c_006813;SPBio_000406;SCHEMBL1851553;CHEMBL3039234;KBio1_001757;KBio2_002190;KBio2_004758;KBio2_007326;KBio3_001413;DTXSID401028831;CCG-38683;LMPK12020013;NCGC00178911-01;Q5454456;(2R,3S)-2-(3,4-Dihydroxyphenyl)-3,7-chromanediol;(2R,3S)-2-(3,4-dihydroxyphenyl)chroman-3,7-diol;BRD-K89853519-001-01-3;2H-1-Benzopyran-3,7-diol,2-(3,4-dihydroxyphenyl)-3,4-dihydro-,(2R,3S)-

Chemical Property of Fisetinidol

Chemical Property:

• Vapor Pressure: 9.49E-14mmHg at 25°C
• Melting Point: 205-206 °C(Solv: ethyl acetate (141-78-6); ligroine (8032-32-4))
• Boiling Point: 568.2 °C at 760 mmHg
• PKA: 9.56±0.10(Predicted)
• Flash Point: 297.4 °C
• PSA: 90.15000
• Density: 1.492 g/cm³
• LogP: 1.84050
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 274.08412354
• Heavy Atom Count: 20
• Complexity: 336

Purity/Quality:

99%, ^*data from raw suppliers

(-)-FISETINIDOL 98.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1C(C(OC2=C1C=CC(=C2)O)C3=CC(=C(C=C3)O)O)O
• Isomeric SMILES: C1[C@@H]([C@H](OC2=C1C=CC(=C2)O)C3=CC(=C(C=C3)O)O)O

Technology Process of Fisetinidol

There total 14 articles about Fisetinidol 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:

2,4-bis(methoxymethoxy)benzaldehyde (13709-06-3) → fisetinidol (490-49-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 50 percent aq. KOH / ethanol / 0.5 h / 20 °C

1.2: 65 percent / ethanol

2.1: H₂ / 5 percent Pd/C / ethanol / 20 °C

2.2: 99 percent / NaBH₄ / ethanol

3.1: thionyl chloride / CH₂Cl₂ / 0.08 h / 20 °C

4.1: 1,8-DBU / benzene / Heating

5.1: 77 percent / AD-mix-α; CH3SO2NH2 / H2O; 2-methyl-propan-2-ol / 24 h / 0 °C

6.1: 3M HCl / H₂O; methanol / 5 h / 60 °C

With hydrogenchloride; potassium hydroxide; AD-mix-α; thionyl chloride; methanesulfonamide; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium on activated charcoal; In methanol; ethanol; dichloromethane; water; tert-butyl alcohol; benzene; 1.1: Metallation / 1.2: Etherification / 2.1: Reduction / 2.2: Reduction / 3.1: Chlorination / 4.1: Elimination / 5.1: Substitution / 6.1: Cyclization;

Reference yield:

1-(3,4-bis(methoxymethoxy)phenyl)ethanone → fisetinidol (490-49-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 50 percent aq. KOH / ethanol / 0.5 h / 20 °C

1.2: 65 percent / ethanol

2.1: H₂ / 5 percent Pd/C / ethanol / 20 °C

2.2: 99 percent / NaBH₄ / ethanol

3.1: thionyl chloride / CH₂Cl₂ / 0.08 h / 20 °C

4.1: 1,8-DBU / benzene / Heating

5.1: 77 percent / AD-mix-α; CH3SO2NH2 / H2O; 2-methyl-propan-2-ol / 24 h / 0 °C

6.1: 3M HCl / H₂O; methanol / 5 h / 60 °C

With hydrogenchloride; potassium hydroxide; AD-mix-α; thionyl chloride; methanesulfonamide; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium on activated charcoal; In methanol; ethanol; dichloromethane; water; tert-butyl alcohol; benzene; 1.1: Metallation / 1.2: Etherification / 2.1: Reduction / 2.2: Reduction / 3.1: Chlorination / 4.1: Elimination / 5.1: Substitution / 6.1: Cyclization;

Reference yield:

2,3',4,4'-tetra-O-methoxymethyl-retro-chalcone (251909-35-0) → fisetinidol (490-49-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: H₂ / 5 percent Pd/C / ethanol / 20 °C

1.2: 99 percent / NaBH₄ / ethanol

2.1: thionyl chloride / CH₂Cl₂ / 0.08 h / 20 °C

3.1: 1,8-DBU / benzene / Heating

4.1: 77 percent / AD-mix-α; CH3SO2NH2 / H2O; 2-methyl-propan-2-ol / 24 h / 0 °C

5.1: 3M HCl / H₂O; methanol / 5 h / 60 °C

With hydrogenchloride; AD-mix-α; thionyl chloride; methanesulfonamide; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium on activated charcoal; In methanol; ethanol; dichloromethane; water; tert-butyl alcohol; benzene; 1.1: Reduction / 1.2: Reduction / 2.1: Chlorination / 3.1: Elimination / 4.1: Substitution / 5.1: Cyclization;

upstream raw materials:

(+)-mollisacacidin

6-Bromo-(-)-fisetinidol

(1S,2S)-syn-1-(3',4'-di-O-methoxymethylphenyl)-3-(2'',4''-di-O-methoxymethylphenyl)-propane-1,2-diol

2,4-bis(methoxymethoxy)benzaldehyde

Downstream raw materials:

6-Phenylselenyl-(-)-fisetinidol

(-)-Fisetinidol-(4α,8)-(+)-catechin 4-O(E)-methyl ether

(2R,3S,4R,2'R,3'S)-2-(3,4-Dihydroxy-phenyl)-2'-(3-hydroxy-4-methoxy-phenyl)-3,4,3',4'-tetrahydro-2H,2'H-[4,6']bichromenyl-3,7,3',5',7'-pentaol

(-)-fisetidinol-(4α,6)-(+)-catechin-O-methyl ether

Refernces

• 1、 Malan, Johannes C. S.,Steenkamp, Jacobus A.,Steynberg, Jan P.,Young, Desmond A.,Brandt, E. Vincent,Ferreira, Daneel. "Oligomeric Flavanoids. Part 8. The First Profisetinidins and Proguibourtinidins Based on C-8 Substituted (-)-Fisetinidol Units and Related c-ring Isomerized Analogues". . p. 209 - 218. Retrieved 2007/10/02.