6,7,4'-Trihydroxyisoflavone

Base Information

• Chemical Name: 6,7,4'-Trihydroxyisoflavone
• CAS No.: 17817-31-1
• Molecular Formula: C15H10 O5
• Molecular Weight: 270.241
• Hs Code.: 2914501900
• UNII: PLM2K574GE
• DSSTox Substance ID: DTXSID8022452
• Nikkaji Number: J254.133E
• Wikidata: Q23055293
• Metabolomics Workbench ID: 22240
• ChEMBL ID: CHEMBL239156
• Mol file: 17817-31-1.mol

Synonyms:6,7,4'-trihydroxyisoflavone;demethyltexasin

Chemical Property of 6,7,4'-Trihydroxyisoflavone

Chemical Property:

• Melting Point: >280℃
• Boiling Point: 587.1°Cat760mmHg
• PKA: 6.85±0.20(Predicted)
• Flash Point: 229.7°C
• PSA: 90.90000
• Density: 1.548g/cm³
• LogP: 2.57680
• Storage Temp.: 2-8°C
• Solubility.: soluble in Dimethylformamide
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 270.05282342
• Heavy Atom Count: 20
• Complexity: 411

Purity/Quality:

98%,99%, ^*data from raw suppliers

Demethyltexasin ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C2=COC3=CC(=C(C=C3C2=O)O)O)O
• Uses: 4'',?6,?7-?Trihydroxyisoflavone is an isoflavone modulator of adenosine-monophosphate-activated protein kinase.

Technology Process of 6,7,4'-Trihydroxyisoflavone

There total 15 articles about 6,7,4'-Trihydroxyisoflavone 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: 92.0%

6,7-dimethoxy-4'-hydroxy-isoflavone (75199-40-5) → 6,7,4'-trihydroxyisoflavone (17817-31-1)

Guidance literature:

With aluminum (III) chloride; dimethylsulfide; In dichloromethane; at 10 - 30 ℃; for 8h; Large scale;

DOI:10.1080/00397911.2014.886331

Reference yield: 60.0%

1-(2,4,5-trihydroxyphenyl)-2-(4'-hydroxyphenyl)ethanone (76095-37-9) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 6,7,4'-trihydroxyisoflavone (17817-31-1)

Guidance literature:

1-(2,4,5-trihydroxyphenyl)-2-(4'-hydroxyphenyl)ethanone; With boron trifluoride diethyl etherate; In N,N-dimethyl-formamide; at 50 - 60 ℃; Cooling with ice;

N,N-dimethyl-formamide; With methanesulfonyl chloride; at 50 - 70 ℃;

DOI:10.1002/cbdv.201400208

Reference yield: 59.2%

C21H20O10 → 6,7,4'-trihydroxyisoflavone (17817-31-1)

Guidance literature:

With sulfonated graphene oxide nanosheets; In water; ethylene glycol; at 105 ℃; for 8h; Reagent/catalyst; Sealed tube;

DOI:10.1002/cctc.201402100

upstream raw materials:

1,3,5-Triazine

1-(2,4,5-trihydroxyphenyl)-2-(4'-hydroxyphenyl)ethanone

glycitein

methanol

Downstream raw materials:

4',6,7-trimethoxy-isoflavone

(+/-)-6-Hydroxy-Equol

2,3-dihydro-6,7,4'-trihydroxyisoflavone

afromosin

Refernces

• 1、 Barková, Kate?ina,Kinne, Matthias,Ullrich, René,Hennig, Lothar,Fuchs, Annett,Hofrichter, Martin. "Regioselective hydroxylation of diverse flavonoids by an aromatic peroxygenase". . p. 4874 - 4878. Retrieved 2011.
• 2、 Chang, Te-Sheng,Chao, Shih-Yu,Chen, Yu-Cheng. "Production of ortho-hydroxydaidzein derivatives by a recombinant strain of Pichia pastoris harboring a cytochrome P450 fusion gene". . p. 426 - 429. Retrieved 2013.
• 3、 Lu, Tzy-Ming,Ko, Horng-Huey,Ng, Lean-Teik,Hsieh, Yen-Pin. "Free-radical-scavenging, antityrosinase, and cellular melanogenesis inhibitory activities of synthetic isoflavones". . p. 963 - 979. Retrieved 2015/06/25.
• 4、 Liu, Jing,Yang, Zhangyou,Luo, Shenglin,Hao, Yuhui,Ren, Jiong,Su, Yongping,Wang, Weidong,Li, Rong. "Facile method for the large-scale synthesis of 6,7,4′-trihydroxyisoflavanone". . p. 3296 - 3303. Retrieved 2015/10/12.