Butein

Base Information

• Chemical Name: Butein
• CAS No.: 487-52-5
• Molecular Formula: C₁₅H₁₂O₅
• Molecular Weight: 272.257
• Hs Code.: 29145090
• European Community (EC) Number: 207-659-5
• UNII: 4WVS5M0LGF
• ChEMBL ID: CHEMBL128000
• DSSTox Substance ID: DTXSID101025569
• Metabolomics Workbench ID: 26587
• NCI Thesaurus Code: C1028
• Nikkaji Number: J277.632D,J11.660B
• NSC Number: 652892
• Wikidata: Q5002498
• Wikipedia: Butein
• Mol file: 487-52-5.mol

Synonyms:2',3,4,4'-tetrahydroxychalcone;2',4',3,4-tetrahydroxychalcone;butein

Chemical Property of Butein

Chemical Property:

• Melting Point: 216°C
• Boiling Point: 560.9°Cat760mmHg
• PKA: 7.44±0.35(Predicted)
• Flash Point: 307.1°C
• PSA: 97.99000
• Density: 1.483g/cm³
• LogP: 2.40510
• Storage Temp.: -20°C
• Solubility.: DMSO: >50 mg/mL
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 272.06847348
• Heavy Atom Count: 20
• Complexity: 367

Purity/Quality:

98%, ^*data from raw suppliers

Butein ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C=C1C=CC(=O)C2=C(C=C(C=C2)O)O)O)O
• Isomeric SMILES: C1=CC(=C(C=C1/C=C/C(=O)C2=C(C=C(C=C2)O)O)O)O
• Uses: Butrin, isobutrin, and butein from medicinal plant Butea monosperma selectively inhibit nuclear factor-κB in activated human mast cells: suppression of tumor necrosis factor-α, interleukin (IL)-6, and IL-8. Anti-inflammatory agent

Technology Process of Butein

There total 52 articles about Butein 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: 78.7%

tetrakis(O-methoxymethyl)butein (124775-23-1) → butein (487-52-5,21849-70-7)

Guidance literature:

With hydrogenchloride; In ethanol; water; for 0.25h; Reflux;

DOI:10.1016/j.bmc.2015.12.024

Reference yield: 72.0%

3,4-di-[(tetrahydro-2H-pyran-2-yl)oxy]-benzaldehyde (61854-89-5) + 2',4'-bis(tetrahydropyran-2-yloxy)acetophenone (136258-01-0) → butein (487-52-5,21849-70-7)

Guidance literature:

With barium hydroxide octahydrate; In methanol; at 40 ℃; for 12h;

DOI:10.1111/j.2042-7158.1997.tb06837.x

Reference yield: 68.0%

2’,3,4,4’-tetraisopropoxychalcone → butein (487-52-5,21849-70-7)

Guidance literature:

With boron trichloride; In hexane; dichloromethane; at -78 - 0 ℃; for 3.5h; Inert atmosphere;

DOI:10.1039/c2ob27163j

upstream raw materials:

dimethylacetylene

2',4'-dihydroxy-4-acetophenone

3,4-dihydroxybenzaldehyde

2'-hydroxy-3,4,4'-trimethoxychalcone

Downstream raw materials:

2-(3,4-dihydroxyphenyl)-7-hydroxychroman-4-one

2'-Hydroxy-4',3,4-triethoxymethoxychalkone

(+/-)-2,3-trans-fustin

dimethylacetylene

Refernces

• 1、 Selvaraj, Baskar,Kim, Dae Won,Huh, Gyuwon,Lee, Heesu,Kang, Kyungsu,Lee, Jae Wook. "Synthesis and biological evaluation of isoliquiritigenin derivatives as a neuroprotective agent against glutamate mediated neurotoxicity in HT22 cells". . . Retrieved 2020/03/05.
• 2、 Kang, Hee,Ku, Jin-Mo,Lee, Jung-hun,Lee, Sukchan,Park, Kye Won,Roh, Kangsan,Song, Youngju. "Synthesis and evaluation of butein derivatives for in vitro and in vivo inflammatory response suppression in lymphedema". . . Retrieved 2020/05/01.