5,7-Dihydroxyisoflavone

Base Information

• Chemical Name: 5,7-Dihydroxyisoflavone
• CAS No.: 4044-00-2
• Molecular Formula: C15H10O4
• Molecular Weight: 254.242
• Hs Code.: 2914400090
• DSSTox Substance ID: DTXSID80418801
• Nikkaji Number: J103.593B
• Wikidata: Q82229489
• Metabolomics Workbench ID: 22297
• ChEMBL ID: CHEMBL1488393
• Mol file: 4044-00-2.mol

Synonyms:5,7-Dihydroxyisoflavone;4044-00-2;5,7-dihydroxy-3-phenylchromen-4-one;5,7-Dihydroxy-3-phenyl-4H-chromen-4-one;Isoflavone, 5,7-dihydroxy-;4H-1-Benzopyran-4-one, 5,7-dihydroxy-3-phenyl-;2-[(2,3-dimethylphenyl)amino]-benzoic acid;2-((2,3-Dimethylphenyl)amino)-Benzoic acid;KBio3_002307;Spectrum_000544;SpecPlus_000102;Spectrum3_001334;Spectrum4_001587;Spectrum5_000274;BSPBio_003087;KBioGR_002174;KBioSS_001024;SPECTRUM240565;DivK1c_006198;N-2,3-Xylyl-Anthranilic acid;SCHEMBL1586459;CHEMBL1488393;KBio1_001142;KBio2_001024;KBio2_003592;KBio2_006160;DTXSID80418801;n-(2,3-xylyl)-anthranilic acid;CHEBI:174348;PJJGZPJJTHBVMX-UHFFFAOYSA-N;BBL036453;CCG-38716;LMPK12050160;STL559003;AKOS005258612;SDCCGMLS-0066480.P001;5,7-Dihydroxy-3-phenyl-chromen-4-one;NCGC00095547-01;NCGC00095547-02;NCGC00095547-03;NCGC00178305-01;N-(2, 3-Dimethylphenyl)anthranilic acid;VS-13495;2-(2,3-Dimethylphenyl)amino-Benzoic acid;CS-0320129;FT-0739136;5,7-Dihydroxy-3-phenyl-4H-chromen-4-one #;2',3'-Dimethyl-2-Diphenylaminecarboxylic acid;5,7-Dihydroxy-3-phenyl-4H-1-benzopyran-4-one, 9CI

Chemical Property of 5,7-Dihydroxyisoflavone

Chemical Property:

• Vapor Pressure: 2.67E-10mmHg at 25°C
• Refractive Index: 1.698
• Boiling Point: 491.9 °C at 760 mmHg
• Flash Point: 192.5 °C
• PSA: 70.67000
• Density: 1.443 g/cm³
• LogP: 2.87120
• XLogP3: 3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 254.05790880
• Heavy Atom Count: 19
• Complexity: 384

Purity/Quality:

99% ^*data from raw suppliers

5,7-Dihydroxyisoflavone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=COC3=CC(=CC(=C3C2=O)O)O

Technology Process of 5,7-Dihydroxyisoflavone

There total 18 articles about 5,7-Dihydroxyisoflavone 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%

2-phenyl-2',4',6'-trihydroxyacetophenone (727-71-9) + orthoformic acid triethyl ester (122-51-0) → 5,7-dihydroxyisoflavone (4044-00-2)

Guidance literature:

With dmap; at 100 ℃; for 4h;

DOI:10.3184/030823408X382135

Reference yield: 81.0%

2-phenyl-2',4',6'-trihydroxyacetophenone (727-71-9) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 5,7-dihydroxyisoflavone (4044-00-2)

Guidance literature:

2-phenyl-2',4',6'-trihydroxyacetophenone; 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: 70.4%

2-phenyl-2',4',6'-trihydroxyacetophenone (727-71-9) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → 5,7-dihydroxyisoflavone (4044-00-2)

Guidance literature:

With boron trifluoride diethyl etherate; In DMF (N,N-dimethyl-formamide); at 50 - 95 ℃; for 1h;

upstream raw materials:

5,7-dimethoxyisoflavone

5,7-dihydroxy-4-oxo-3-phenyl-4H-chromene-2-carboxylic acid

2-hydroxy-4,6-dimethoxyphenyl benzyl ketone

2-phenyl-2',4',6'-trihydroxyacetophenone

Downstream raw materials:

5-hydroxy-7-(methoxymethoxy)-3-phenyl-4H-chromen-4-one

5-methoxy-4-oxo-3-phenyl-4H-chromen-7-yl dimethylcarbamate

7-hydroxy-5-methoxy-3-phenyl-4H-chromen-4-one

7-hydroxy-8-[(dimethylamino)methyl]-5-methoxy-3-phenyl-4H-chromen-4-one

Refernces

• 1、 Jia, Hongge,Ma, Liqun,Shi, Yongqiang,Song, Heming,Tang, Yanan,Wang, Qingji,Wang, Yazhen,Xu, Shuangping,Yang, Guoxing,Zang, Yu,Zhao, Xinyi. "The oxidative coupling between benzaldehyde derivatives and phenylacetylene catalyzed by rhodium complexes via C-H bond activation". . p. 20 - 25. Retrieved 2020/03/30.
• 2、 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.