Xanthomicrol

Base Information

• Chemical Name: Xanthomicrol
• CAS No.: 16545-23-6
• Molecular Formula: C18H16 O7
• Molecular Weight: 344.321
• Hs Code.: 2914509090
• NSC Number: 79323
• UNII: 3IN82Y8CAA
• DSSTox Substance ID: DTXSID20167947
• Nikkaji Number: J14.449E
• Wikidata: Q27116387
• Metabolomics Workbench ID: 24530
• ChEMBL ID: CHEMBL476121
• Mol file: 16545-23-6.mol

Synonyms:xanthomicrol

Chemical Property of Xanthomicrol

Chemical Property:

• Melting Point: 225 °C
• Boiling Point: 609.9°Cat760mmHg
• PKA: 6.85±0.40(Predicted)
• Flash Point: 225°C
• PSA: 98.36000
• Density: 1.387g/cm³
• LogP: 2.89700
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 344.08960285
• Heavy Atom Count: 25
• Complexity: 512

Purity/Quality:

99% ^*data from raw suppliers

5,4'-Dihydroxy-6,7,8-trimethoxyflavone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C(=C2C(=C1O)C(=O)C=C(O2)C3=CC=C(C=C3)O)OC)OC
• Uses: Xanthomicrol inhibits growth of human prostate cancer LNCaP cells by epigenetically restoring p21 gene expression and inhibiting cancer stem-like cell proliferation.

Technology Process of Xanthomicrol

There total 10 articles about Xanthomicrol 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: 87.0%

4'-benzyloxy-5,6,7,8-tetramethoxyflavone (40110-96-1) → xanthomicrol (16545-23-6)

Guidance literature:

4'-benzyloxy-5,6,7,8-tetramethoxyflavone; With boron trichloride; In dichloromethane; toluene; at -78 - 20 ℃; for 12h; Inert atmosphere;

With water; sodium hydroxide; In dichloromethane; toluene; at 20 ℃; for 0.5h;

DOI:10.1016/j.bmc.2011.10.001

Reference yield:

2-hydroxy-3,4,5,6-tetramethoxyacetophenone (3162-28-5) → xanthomicrol (16545-23-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.0 g / KOH / aq. ethanol / Ambient temperature

2: 450 mg / 85percent H₃PO₄ / ethanol / 50 h / Heating

3: 350 mg / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / dioxane / 10 h / Heating

4: 120 mg / H₂ / Pd-C / ethyl acetate

5: AlCl₃ / nitrobenzene / Ambient temperature

With potassium hydroxide; aluminium trichloride; phosphoric acid; hydrogen; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium on activated charcoal; In 1,4-dioxane; ethanol; ethyl acetate; nitrobenzene;

DOI:10.1248/cpb.28.717

Reference yield:

p-benzyloxybenzaldehyde (4397-53-9) → xanthomicrol (16545-23-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.0 g / KOH / aq. ethanol / Ambient temperature

2: 450 mg / 85percent H₃PO₄ / ethanol / 50 h / Heating

3: 350 mg / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / dioxane / 10 h / Heating

4: 120 mg / H₂ / Pd-C / ethyl acetate

5: AlCl₃ / nitrobenzene / Ambient temperature

With potassium hydroxide; aluminium trichloride; phosphoric acid; hydrogen; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium on activated charcoal; In 1,4-dioxane; ethanol; ethyl acetate; nitrobenzene;

DOI:10.1248/cpb.28.717

upstream raw materials:

4'-hydroxy-5,6,7,8-tetramethoxy flavone

p-benzyloxybenzaldehyde

4'-benzyloxy-5,6,7,8-tetramethoxyflavone

4-benzyloxy-2'-hydroxy-3',4',5',6'-tetramethoxychalcone

Downstream raw materials:

gardenin B

tangeritin

6,7-dimethoxy-5,8,4′-trihydroxyflavone

8-demethylthymusin

Refernces

• 1、 Iinuma,Matsuura,Kurogochi,Tanaka. "Studies on the constituents of useful plants. V. Multisubstituted flavones in the fruit peel of Citrus reticulata and their examination by gas-liquid chromatography". . p. 717 - 722. Retrieved 2007/10/02.