Flavokawain B

Base Information

• Chemical Name: Flavokawain B
• CAS No.: 76554-24-0
• Molecular Formula: C₁₇H₁₆O₄
• Molecular Weight: 284.312
• NSC Number: 51351
• UNII: R9WC6SM4UQ
• DSSTox Substance ID: DTXSID601028794
• Nikkaji Number: J647.133A,J816.775C
• Wikipedia: Flavokavain_B
• Wikidata: Q5458167
• Metabolomics Workbench ID: 26722
• ChEMBL ID: CHEMBL104255
• Mol file: 76554-24-0.mol

Synonyms:flavokavain B;flavokavin B;flavokawain B

Chemical Property of Flavokawain B

Chemical Property:

• XLogP3: 3.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 284.10485899
• Heavy Atom Count: 21
• Complexity: 360

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=C(C(=C1)OC)C(=O)C=CC2=CC=CC=C2)O
• Isomeric SMILES: COC1=CC(=C(C(=C1)OC)C(=O)/C=C/C2=CC=CC=C2)O

Technology Process of Flavokawain B

There total 16 articles about Flavokawain 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: 100.0%

C20H22O4 → 1-(2-hydroxy-4,6-dimethoxyphenyl)-3-phenylpropenone (1775-97-9,76554-24-0)

Guidance literature:

With boron trichloride; In dichloromethane; at 0 ℃;

DOI:10.3390/molecules200712512

Reference yield: 90.0%

2-hydroxy-4,6-dimethoxyacetophenone (90-24-4) + benzaldehyde (100-52-7) → 1-(2-hydroxy-4,6-dimethoxyphenyl)-3-phenylpropenone (1775-97-9,76554-24-0)

Guidance literature:

2-hydroxy-4,6-dimethoxyacetophenone; benzaldehyde; With potassium hydroxide; In ethanol; water; for 18h;

With hydrogenchloride; In ethanol; water; pH=3-4; Cooling with ice;

DOI:10.1016/j.bmcl.2014.07.087

Reference yield: 78.0%

3,5-dimethoxyphenol (500-99-2) + cinnamoyl chloride (102-92-1,17082-09-6) → 1-(2-hydroxy-4,6-dimethoxyphenyl)-3-phenylpropenone (1775-97-9,76554-24-0)

Guidance literature:

With boron trifluoride diethyl etherate; In toluene; for 3h; Reflux;

DOI:10.3184/174751915X14307337733513

upstream raw materials:

2-hydroxy-4,6-dimethoxyacetophenone

benzaldehyde

3,5-dimethoxy-2-(trimethylsilyl)phenyl trifluoromethanesulfonate

Cinnamic acid

Downstream raw materials:

5,7-dihydroxy-2-phenyl-chromen-4-one

Refernces

• 1、 Hamzah, Ahmad Sazali,Md Idris, Muhd Hanis,Mohd Amin, Siti Norhidayah,Mohd Amin, Siti Norhidayu,Salleh, Mohd Zaki,Selvaraj, Manikandan,Shaameri, Zurina,Teh, Lay Kek,Wibowo, Agustono,Zakaria, Zainul Amiruddin. "Discovery of polymethoxyflavones as potential cyclooxygenase-2 (COX-2), 5-lipoxygenase (5-LOX) and phosphodiesterase 4B (PDE4B) inhibitors". . . Retrieved 2021/08/06.
• 2、 ?uz?ny, Mateusz,Henklewska, Marta,Janeczko, Tomasz,Koz?owska, Ewa,Obmińska-Mrukowicz, Bozena,Pawlak, Aleksandra,Suárez, Beatriz Hernández. "Chalcone methoxy derivatives exhibit antiproliferative and proapoptotic activity on canine lymphoma and leukemia cells". . . Retrieved 2020/10/12.