Luteone

Base Information

• Chemical Name: Luteone
• CAS No.: 41743-56-0
• Molecular Formula: C20H18O6
• Molecular Weight: 354.359
• Hs Code.: 2914501900
• UNII: FU3E0232IF
• ChEMBL ID: CHEMBL549617
• DSSTox Substance ID: DTXSID00194574
• Metabolomics Workbench ID: 22424
• Nikkaji Number: J16.475E
• Wikidata: Q6705431
• Wikipedia: Luteone_(isoflavone)
• Mol file: 41743-56-0.mol

Synonyms:Luteone;41743-56-0;Luteone (isoflavone);UNII-FU3E0232IF;FU3E0232IF;CHEBI:27917;3-(2,4-dihydroxyphenyl)-5,7-dihydroxy-6-(3-methylbut-2-enyl)chromen-4-one;DTXSID00194574;3-(2,4-dihydroxyphenyl)-5,7-dihydroxy-6-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one;4H-1-Benzopyran-4-one, 3-(2,4-dihydroxyphenyl)-5,7-dihydroxy-6-(3-methyl-2-butenyl)-;3-(2,4-dihydroxyphenyl)-5,7-dihydroxy-6-(3-methylbut-2-en-1-yl)-4H-chromen-4-one;6-isopentenyl-2'-hydroxygenistein;uncinanone A;Luteone?;CHEMBL549617;MEGxp0_000744;SCHEMBL1667408;ACon1_000606;DTXCID40117065;GLXC-17705;HY-N3353;LMPK12050287;AKOS032948669;FS-9882;NCGC00168918-01;CS-0023971;FT-0639733;A825642;Q6705431;BRD-K34029608-001-01-8;B0005-117275;3-(2,4-Dihydroxyphenyl)-5,7-dihydroxy-6-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one, 9CI;3-(2,4-dihydroxyphenyl)-5,7-dihydroxy-6-(3-methylbut-2-enyl)-1-benzopyran-4-one;3-(2,4-dihydroxyphenyl)-5,7-dihydroxy-6-(3-methylbut-2-enyl)-4H-chromen-4-one

Chemical Property of Luteone

Chemical Property:

• Vapor Pressure: 9.39E-17mmHg at 25°C
• Refractive Index: 1.69
• Boiling Point: 635.7 °C at 760 mmHg
• Flash Point: 230.8 °C
• PSA: 111.13000
• Density: 1.424 g/cm³
• LogP: 3.79110
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 354.11033829
• Heavy Atom Count: 26
• Complexity: 593

Purity/Quality:

98%min ^*data from raw suppliers

Luteone 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCC1=C(C2=C(C=C1O)OC=C(C2=O)C3=C(C=C(C=C3)O)O)O)C

Technology Process of Luteone

There total 19 articles about Luteone 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: 66.0%

2',4',7-tris(benzoyloxy)-5-hydroxy-6-(3-methyl-2-butenyl)isoflavone (321570-06-3) → luteone (41743-56-0)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; methanol; at 20 ℃; for 1h;

DOI:10.1248/cpb.52.1285

Reference yield:

dimethylallyl diphosphate (358-72-5) + 2',4',5,7-tetrahydroxyisoflavone (1156-78-1) → luteone (41743-56-0)

Guidance literature:

With recombinant Cudrania tricuspidata isoliquiritigenin 3'-dimethylallyltransferase; magnesium chloride; In aq. buffer; at 30 ℃; for 16h; pH=9; Reagent/catalyst; regioselective reaction; Enzymatic reaction;

DOI:10.1074/jbc.M114.608265

Reference yield:

2',4',5,7-tetrakis(benzyloxy)-6-iodoisoflavone (321569-95-3) → luteone (41743-56-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 96 percent / H₂ / Pd/C / methanol; dioxane / 20 °C

2: 85 percent / K₂CO₃ / acetone / 0.5 h / Heating

3: 91 percent / K₂CO₃ / acetone / 0.33 h / Heating

4: TsOH*H₂O; AcOH / toluene / 0.75 h / 110 °C

5: 95 percent / BCl₃ / CH₂Cl₂ / 0.25 h / 15 °C

6: 66 percent / aq. NaOH / methanol; dioxane / 1 h / 20 °C

With sodium hydroxide; hydrogen; boron trichloride; potassium carbonate; toluene-4-sulfonic acid; acetic acid; palladium on activated charcoal; In 1,4-dioxane; methanol; dichloromethane; acetone; toluene;

DOI:10.1248/cpb.52.1285

upstream raw materials:

2',4',7-tris(benzoyloxy)-5-hydroxy-6-(3-methyl-2-butenyl)isoflavone

2',4'-dihydroxy-6'-(methoxymethoxy)acetophenone

4',6'-bis(benzyloxy)-2'-(methoxymethoxy)acetophenone

2',4',5,7-tetrahydroxy-6-(3-hydroxy-3-methylbutyl)isoflavone

Downstream raw materials:

6-(2,4-Dihydroxy-phenyl)-4-hydroxy-2-(1-hydroxy-1-methyl-ethyl)-2,3-dihydro-furo[3,2-g]chromen-5-one

6-(2,3-Dihydroxy-3-methyl-butyl)-3-(2,4-dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-one

2',4',5,7-tetraacetoxy-6-(3-methyl-2-butenyl)isoflavone

3-(2,4-Dihydroxy-phenyl)-5,7-dihydroxy-6-(4-hydroxy-3-hydroxymethyl-but-2-enyl)-chromen-4-one

Refernces

• 1、 Tsukayama, Masao,Wada, Hironari,Kawamura, Yasuhiko,Yamashita, Kazuyo,Nishiuchi, Masaki. "Regioselective synthesis of 6-alkyl- and 6-prenylpolyhydroxyisoflavones and 6-alkylcoumaronochromone derivatives". . p. 1285 - 1289. Retrieved 2007/10/03.