Flavan-3-ol

Base Information

• Chemical Name: Flavan-3-ol
• CAS No.: 1481-83-0
• Molecular Formula: C15H14O2
• Molecular Weight: 226.275
• Nikkaji Number: J650.404C
• Wikidata: Q27149144
• Mol file: 1481-83-0.mol

Synonyms:2H-1-benzopyran-3-ol, 3,4-dihydro-2-phenyl-;3,4-dihydro-2-phenyl-2H-1-benzopyran-3-ol;3-flavan-ol;3-flavanol;3-flavanol (mixed isomers);flavan-3-ol

Chemical Property of Flavan-3-ol

Chemical Property:

• Vapor Pressure: 6.14E-07mmHg at 25°C
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 226.099379685
• Heavy Atom Count: 17
• Complexity: 247

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(OC2=CC=CC=C21)C3=CC=CC=C3)O

Technology Process of Flavan-3-ol

There total 9 articles about Flavan-3-ol 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:

2-phenyl-3-oxo-3,4-dihydro-2H-1-benzopyran (20760-17-2) → cis-flavan-3-ol (1481-83-0,13328-95-5,55568-96-2,55568-98-4,88244-15-9,116002-72-3)

Guidance literature:

With L-Selectride; In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1016/j.bmcl.2014.03.088

Reference yield:

(E)-2'-hydroxy-chalcone (888-12-0) → flavan-3-ol (1481-83-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaBH₄ / tetrahydrofuran; ethanol

2.1: BH₃*THF

2.2: aq. H₂O₂; NaOH

With sodium tetrahydroborate; borane-THF; In tetrahydrofuran; ethanol;

DOI:10.1007/s00018-005-5422-7

Reference yield:

o-hydroxyacetophenone (118-93-4,104809-67-8) → flavan-3-ol (1481-83-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: NaH / dimethylformamide / 0 °C

2.1: NaBH₄ / tetrahydrofuran; ethanol

3.1: BH₃*THF

3.2: aq. H₂O₂; NaOH

With sodium tetrahydroborate; borane-THF; sodium hydride; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide;

DOI:10.1007/s00018-005-5422-7

upstream raw materials:

2-phenylchromene

(E)-2'-hydroxy-chalcone

o-hydroxyacetophenone

benzaldehyde

Refernces

• 1、 Dell'Agli,Bellosta,Rizzi,Galli,Canavesi,Rota,Parente,Bosisio,Romeo. "A structure-activity study for the inhibition of metalloproteinase-9 activity and gene expression by analogues of gallocatechin-3-gallate". . p. 2896 - 2903. Retrieved 2007/10/03.