Limocitrol

Base Information

• Chemical Name: Limocitrol
• CAS No.: 549-10-0
• Molecular Formula: C18H16O9
• Molecular Weight: 376.31
• UNII: 113VHU3N34
• DSSTox Substance ID: DTXSID301131225
• Metabolomics Workbench ID: 26416
• Nikkaji Number: J11.571A
• Wikidata: Q27251238
• Mol file: 549-10-0.mol

Synonyms:Limocitrol;549-10-0;113VHU3N34;UNII-113VHU3N34;3,5,7,4'-Tetrahydroxy-6,8,3'-trimethoxyflavone;3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-6,8-dimethoxychromen-4-one;4H-1-Benzopyran-4-one, 3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-6,8-dimethoxy-;3,5,7-Trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-6,8-dimethoxy-4H-1-benzopyran-4-one;3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-6,8-dimethoxy-4H-chromen-4-one;CHEBI:168259;DTXSID301131225;LMPK12113333;AKOS040752576;3,4',5,7-Tetrahydroxy-3',6,8-trimethoxyflavone;Q27251238

Chemical Property of Limocitrol

Chemical Property:

• PSA: 138.82000
• LogP: 2.30820
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 4
• Exact Mass: 376.07943208
• Heavy Atom Count: 27
• Complexity: 591

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=CC(=C1)C2=C(C(=O)C3=C(C(=C(C(=C3O2)OC)O)OC)O)O)O

Technology Process of Limocitrol

There total 17 articles about Limocitrol 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: 100.0%

7-Benzyloxy-2-(4-benzyloxy-3-methoxy-phenyl)-3,5-dihydroxy-6,8-dimethoxy-chromen-4-one (176662-29-6) → 3,5,7,4'-Tetrahydroxy-6,8,3'-trimethoxyflavone (549-10-0)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; ethyl acetate; Ambient temperature;

DOI:10.1246/bcsj.69.1033

Reference yield:

7-benzyloxy-2-(4-benzyloxy-3-methoxy-phenyl)-5,6,8-trimethoxy-chromen-4-one (4396-78-5) → 3,5,7,4'-Tetrahydroxy-6,8,3'-trimethoxyflavone (549-10-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) dimethyldioxirane, 2.) p-TsOH / 1.) CH₂Cl₂, Me₂CO, 0 deg C, 12 h, 2.) CH₂Cl₂, 0 deg C, 30 min

2: 100 percent / K₂CO₃ / acetone / 2 h / Heating

3: 100 percent / AlBr₃ / acetonitrile / 0.83 h / 0 °C

4: 100 percent / K₂CO₃ / methanol / 0.67 h / 70 °C

5: 100 percent / H₂ / 10percent Pd/C / ethyl acetate; methanol / Ambient temperature

With aluminum tri-bromide; hydrogen; 3,3-dimethyldioxirane; potassium carbonate; toluene-4-sulfonic acid; palladium on activated charcoal; In methanol; ethyl acetate; acetone; acetonitrile;

DOI:10.1246/bcsj.69.1033

Reference yield:

2,3-diacetoxy-1,4,5-trimethoxy-benzene (56002-82-5) → 3,5,7,4'-Tetrahydroxy-6,8,3'-trimethoxyflavone (549-10-0)

Guidance literature:

Multi-step reaction with 17 steps

1: 77 percent / K₂CO₃ / acetone; dimethylformamide / 50 h / Heating

2: 10percent aq. NaOH / methanol / 0.5 h / Ambient temperature

3: K₂CO₃ / acetone / 3 h / Heating

4: H₂ / 10percent Pd/C / methanol; ethyl acetate / Ambient temperature

5: pyridine

6: 1.) AcOH, BF₃(g), 2.) pyridine / 1.) from 50 to 60 deg C, 5 h

7: 10percent aq. NaOH / methanol / 0.25 h / Ambient temperature

8: (i-Pr)2NEt / CH₂Cl₂ / 0.83 h / 5 °C

9: pyridine / 3 h / 60 - 70 °C

10: KOH, pyridine / 2 h / 60 °C

11: conc. H₂SO₄, HOAc / 1 h / 50 °C

12: 80 percent / K₂CO₃ / dimethylformamide / 0.08 h / 150 °C

13: 1.) dimethyldioxirane, 2.) p-TsOH / 1.) CH₂Cl₂, Me₂CO, 0 deg C, 12 h, 2.) CH₂Cl₂, 0 deg C, 30 min

14: 100 percent / K₂CO₃ / acetone / 2 h / Heating

15: 100 percent / AlBr₃ / acetonitrile / 0.83 h / 0 °C

16: 100 percent / K₂CO₃ / methanol / 0.67 h / 70 °C

17: 100 percent / H₂ / 10percent Pd/C / ethyl acetate; methanol / Ambient temperature

With pyridine; potassium hydroxide; sodium hydroxide; aluminum tri-bromide; sulfuric acid; boron trifluoride; hydrogen; 3,3-dimethyldioxirane; potassium carbonate; toluene-4-sulfonic acid; acetic acid; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1246/bcsj.69.1033

upstream raw materials:

7-Benzyloxy-2-(4-benzyloxy-3-methoxy-phenyl)-3,5-dihydroxy-6,8-dimethoxy-chromen-4-one

7-benzyloxy-2-(4-benzyloxy-3-methoxy-phenyl)-5,6,8-trimethoxy-chromen-4-one

2,3-diacetoxy-1,4,5-trimethoxy-benzene

1,2-dihydroxy-3,4,6-trimethoxybenzene

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