81267-65-4

Basic information

• Product Name: Phenoxodiol
• Synonyms: DEHYDROEQUOL;7,4'-DIHYDROXYISOFLAV-3-ENE;PHENOXODIOL;Haginin E;Idronoxil;3-(4-Hydroxyphenyl)-2H-1-benzopyran-7-ol;Phenoxodiol Haginin E Idronoxil;2H-1-Benzopyran-7-ol, 3-(4-hydroxyphenyl)-
• CAS NO: 81267-65-4
• Molecular Formula: C₁₅H₁₂O₃
• Molecular Weight: 240.25
• Product Categories: Flavones
• Mol File: 81267-65-4.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 463.7oC at 760 mmHg
• Flash Point: 234.3oC
• Appearance: white to light brown/
• Density: 1.337g/cm3
• Vapor Pressure: 3.2E-09mmHg at 25°C
• Refractive Index: 1.679
• Storage Temp.: room temp
• Solubility: DMSO: soluble10mg/mL, clear
• CAS DataBase Reference: Phenoxodiol(CAS DataBase Reference)
• NIST Chemistry Reference: Phenoxodiol(81267-65-4)
• EPA Substance Registry System: Phenoxodiol(81267-65-4)

Safety Data

• Hazard Codes: Xn,N
• Statements: 22-50
• Safety Statements: 61
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 81267-65-4(Hazardous Substances Data)

Usage

Uses

Antineoplastic which acts as an antiproliferative, topoisomerase II inhibitor; 5 reductase inhibitor[Note— The trivial name, phenoxodiol, has appeared in literature].

InChI:InChI=1/C15H12O3/c16-13-4-1-10(2-5-13)12-7-11-3-6-14(17)8-15(11)18-9-12/h1-8,16-17H,9H2

Upstream product

• 17720-60-4 2,4,4'-trihydroxy deoxybenzoin 
• 156-38-7 4-hydroxyphenylacetate 
• 1179998-29-8 7-benzyloxy-3-(4-benzyloxyphenyl)chromen-4-one 
• 486-66-8 daidzein 
• 151884-07-0 2',4'-dihydroxy-3-chloropropiophenone 
• 124887-46-3 3-bromo-2,3-dihydro-7-hydroxy-4H-1-benzopyran-4-one 
• 873426-76-7 tert-butyldimethylsilyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl ether 
• 1450994-70-3 (3-bromo-2H-chromen-7-yloxy)(tert-butyl)dimethylsilane 
• 269409-70-3 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol 
• 76240-27-2 7-hydroxy-2,3-dihydro-4H-chromen-4-one 
• 108-46-3 recorcinol 
• 498548-56-4 2-(4-((tert-butyldimethylsilyl)-oxy)phenyl)acetaldehyde 
• 96013-75-1 2-(4{[tert-butyl(dimethyl)silyl]oxy}phenyl)ethanol 
• 1370331-09-1 4',7-di-tert-butyldimethylsilyloxy-2-morpholinoisoflav-3-ene 

Downstream Products

• 1055327-33-7 4-(3-(4-methoxybenzyl)-2,3,4,8-tetrahydrochromeno[6,7-e][1,3]oxazin-7-yl)phenol 
• 1055327-42-8 4-(3-(4-chlorobenzyl)-2,3,4,8-tetrahydrochromeno[6,7-e][1,3]oxazin-7-yl)phenol 
• 1055327-55-3 4-(3-(4-tert-butylphenyl)-2,3,4,8-tetrahydrochromeno[6,7-e][1,3]oxazin-7-yl)phenol 
• 1055327-29-1 4-(3-(1-phenylethyl)-2,3,4,8-tetrahydrochromeno[6,7-e][1,3]oxazin-7-yl)phenol 
• 1055327-34-8 4-(3-phenyl-2,3,4,8-tetrahydrochromeno[6,7-e][1,3]oxazin-7-yl)phenol 
• 1055327-59-7 4-(3-(4-methoxyphenyl)-2,3,4,8-tetrahydrochromeno[6,7-e][1,3]oxazin-7-yl)phenol 
• 1055327-30-4 4-(3-propyl-2,3,4,8-tetrahydrochromeno[6,7-e][1,3]oxazin-7-yl)phenol 
• 1055327-28-0 4-(3-benzyl-2,3,4,8-tetrahydrochromeno[6,7-e][1,3]oxazin-7-yl)phenol 
• 1055327-35-9 4,4'-(chromeno[6,7-e][1,3]oxazine-3,7(2H,4H,8H)-diyl)diphenol 
• 1055327-31-5 4-(3-methyl-2,3,4,8-tetrahydrochromeno[6,7-e][1,3]oxazin-7-yl)phenol 
• 1055327-45-1 4-(3-p-tolyl-2,3,4,8-tetrahydrochromeno[6,7-e][1,3]oxazin-7-yl)phenol 
• 1055327-57-5 4-(3-(naphth-1-yl-methyl)-2,3,4,8-tetrahydrochromeno[6,7-e][1,3]oxazin-7-yl)phenol 
• 1055327-50-8 4-(3-(3-nitrophenyl)-2,3,4,8-tetrahydrochromeno[6,7-e][1,3]oxazin-7-yl)phenol 
• 1055327-43-9 4-(3-(3-methoxypropyl)-2,3,4,8-tetrahydrochromeno[6,7-e][1,3]oxazin-7-yl)phenol 

Relevant articles and documents

Structure–activity relationship of phytoestrogen analogs as ERα/β agonists with neuroprotective activities

A set of isoflavononid and flavonoid analogs was prepared and evaluated for estrogen receptor α (ERα) and ERβ transactivation and anti-neuroinflammatory activities. Structure–activity relationship (SAR) study of naturally occurring phytoestrogens, their metabolites, and related isoflavone analogs revealed the importance of the C-ring of isoflavonoids for ER activity and selectivity. Docking study suggested putative binding modes of daidzein 2 and dehydroequol 8 in the active site of ERα and ERβ, and provided an understanding of the promising activity and selectivity of dehydroequol 8. Among the tested compounds, equol 7 and dehydroequol 8 were the most potent ERα/β agonists with ERβ selectivity and neuroprotective activity. This study provides knowledge on the SAR of isoflavonoids for further development of potent and selective ER agonists with neuroprotective potential.

Total synthesis of eryvarin H and its derivatives and their biological activity as ERRγ inverse agonist

Total synthesis of eryvarin H and a biological investigation of its analogues as a potential inverse agonist of ERRγ are described here. Among the 13 analogues prepared by the modular synthetic route, eryvarin H and compound 12 showed meaningful ERRγ inverse agonistic activities along with moderate selectivity over ERα and other nuclear receptors in the cell-based reporter gene assay.

Processes for Preparing Isoflavonoids using 7-benzyloxy-3-(4-methoxyphenyl)-2H-1-benzopyran as a Starting Material

Disclosed herein are processes for the preparation of isoflavonoids, in particular haginin E, equol, daidzein, formononetin and the like, in which 7-benzyloxy-3-(4-methoxyphenyl)-2H-1-benzopyran is used as a common starting material.