Cannflavin B

Base Information

• Chemical Name: Cannflavin B
• CAS No.: 76735-58-5
• Molecular Formula: C₂₁H₂₀O₆
• Molecular Weight: 368.386
• NSC Number: 719330
• UNII: KK2PPP6QRW
• DSSTox Substance ID: DTXSID201317814
• Nikkaji Number: J987.905F
• Wikidata: Q105122046
• Metabolomics Workbench ID: 23878
• ChEMBL ID: CHEMBL1985794
• Mol file: 76735-58-5.mol

Synonyms:cannflavin;cannflavin A;cannflavin B

Chemical Property of Cannflavin B

Chemical Property:

• XLogP3: 4.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 368.12598835
• Heavy Atom Count: 27
• Complexity: 608

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=CCC1=C(C2=C(C=C1O)OC(=CC2=O)C3=CC(=C(C=C3)O)OC)O)C

Technology Process of Cannflavin B

There total 7 articles about Cannflavin B 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: 84.0%

6-C-prenyl-3',7-bis-O-methoxymethylchrysoeriol → 6-prenylchrysoeriol (76735-58-5)

Guidance literature:

With hydrogenchloride; In methanol; water; for 4h;

DOI:10.1016/j.tetlet.2019.151138

Reference yield:

C26H28O7 → 6-prenylchrysoeriol (76735-58-5)

Guidance literature:

With pyrrolidine; In tetrahydrofuran; for 2h; Inert atmosphere; Reflux;

DOI:10.1021/ol800665w

Reference yield:

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on (491-70-3) → 6-prenylchrysoeriol (76735-58-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: potassium carbonate / acetone / 0.5 h / 20 °C

1.2: 20 °C

2.1: potassium carbonate / acetone / 2 h / 20 °C

3.1: potassium carbonate / acetone / 0.5 h / 20 °C

3.2: 4 h / 45 °C

4.1: montmorillonite K₁₀ Clay / toluene / 4 h / Inert atmosphere; Reflux

5.1: hydrogenchloride / methanol; water / 4 h

With hydrogenchloride; montmorillonite K₁₀ Clay; potassium carbonate; In methanol; water; acetone; toluene;

DOI:10.1016/j.tetlet.2019.151138

upstream raw materials:

dimethylallyl diphosphate

chrysoeriol

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

Refernces

• 1、 Li, Wei,Shu, Liang,Liu, Kexiong,Wang, Qiuan. "Regioselective synthesis of C-prenylated flavonoids via intramolecular [1,3] or [1,5] shift reaction catalyzed by acidic clays". . . Retrieved 2019/09/17.
• 2、 Minassi, Alberto,Giana, Anna,Ech-Chahad, Abdellah,Appendino, Giovanni. "A regiodivergent synthesis of ring A C-prenylflavones". supporting information; experimental part. p. 2267 - 2270. Retrieved 2009/05/26.