17720-60-4

Basic information

• Product Name: 1-(2,4-DIHYDROXY-PHENYL)-2-(4-HYDROXY-PHENYL)-ETHANONE
• Synonyms: 1-(2,4-DIHYDROXY-PHENYL)-2-(4-HYDROXY-PHENYL)-ETHANONE;OTAVA-BB BB7020210418;1-(2,4-DIHYDROXYPHENYL)-2-(4-HYDROXYPHENYL)ETHAN-1-ONE;1-(2,4-Dihydroxyphenyl)-2-2-(4-hydroxyphenyl)ethanone;2,4,4'-Trihydroxydeoxybenzoin;2',4'-Dihy;2,4-Dihydroxyphenyl 4'-hydroxybenzyl ketone;Acetophenone,2',4'-dihydroxy-2-(p-hydroxyphenyl)- (6CI,7CI,8CI)
• CAS NO: 17720-60-4
• Molecular Formula: C₁₄H₁₂O₄
• Molecular Weight: 244.24
• EINECS: 216-004-2
• Mol File: 17720-60-4.mol
• Article Data: 30

Chemical Properties

• Melting Point: 192 °C
• Boiling Point: 499°Cat760mmHg
• Flash Point: 269.7°C
• Appearance: /Solid
• Density: 1.380
• Vapor Pressure: 1.4E-10mmHg at 25°C
• Refractive Index: 1.674
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 7.62±0.35(Predicted)
• CAS DataBase Reference: 1-(2,4-DIHYDROXY-PHENYL)-2-(4-HYDROXY-PHENYL)-ETHANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2,4-DIHYDROXY-PHENYL)-2-(4-HYDROXY-PHENYL)-ETHANONE(17720-60-4)
• EPA Substance Registry System: 1-(2,4-DIHYDROXY-PHENYL)-2-(4-HYDROXY-PHENYL)-ETHANONE(17720-60-4)

Safety Data

• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 36/37
• Hazardous Substances Data: 17720-60-4(Hazardous Substances Data)

Usage

Preparation

Preparation by reaction of p-hydroxyphenylacetic acid with resorcinol in the presence of boron trifluoride etherate under argon on a water bath for 1 h (98%), at 100° for 1 h (70%) or for 15 min (40%).

InChI:InChI=1/C14H12O4/c15-10-3-1-9(2-4-10)7-13(17)12-6-5-11(16)8-14(12)18/h1-6,8,15-16,18H,7H2

Upstream product

• 67804-60-8 1-(2,4-dimethoxyphenyl)-2-(4-methoxyphenyl)ethanone 
• 829-20-9 2',4'-dimethoxyacetophenone 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 156-38-7 4-hydroxyphenylacetate 
• 108-46-3 recorcinol 
• 487-49-0 1-(2,4-dihydroxyphenyl)-2-(4-methoxyphenyl)ethanone 
• 14191-95-8 4-cyanomethylphenol 
• 111797-19-4 3-(2,4-dimethoxy-phenyl)-2-(4-methoxy-phenyl)-3-oxo-propionic acid ethyl ester 
• 140-53-4 p-chlorobenzyl cyanide 

Downstream Products

• 486-66-8 daidzein 
• 130064-21-0 1-(2-hydroxy-4-((tetrahydro-2H-pyran-2-yl)oxy)phenyl)-2-(4-((tetrahydro-2H-pyran-2-yl)oxy)phenyl)ethanone 
• 883717-77-9 1-[2-hydroxy-4-(tetrahydro-2H-pyran-2-yloxy)phenyl]-2-[4-(tetrahydro-2H-pyran-2-yloxy)phenyl]ethanone oxime 
• 1352307-39-1 3-(4-hydroxyphenyl)-4-methyl-2-(4-((S)-2-((R)-3-methylpyrrolidin-1-yl)propoxy)phenyl)-2H-chromen-7-ol trifluoroacetate 
• 81267-65-4 idronoxil 
• 17238-05-0 dihydrodaidzein 
• 531-95-3 equol 
• 252353-08-5 chalcone 
• 1443752-88-2 C₂₉H₃₃NO₁₀P₂ 
• 1443752-91-7 C₂₉H₃₃NO₁₀P₂ 
• 1443752-92-8 C₃₉H₄₇NO₆ 
• 1443752-93-9 C₃₅H₃₉NO₈ 
• 1443752-90-6 C₂₉H₃₁NO₅ 
• 1443752-79-1 (2S)-3-(4-hydroxyphenyl)-4-methyl-2-(4-{2-[(3R)-3-methylpyrrolidin-1-yl]ethoxy}phenyl)-2H-chromen-7-ol hydrochloride 

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.

A Direct Synthesis of 2-(ω-Carboxyalkyl)isoflavones from ortho-Hydroxylated Deoxybenzoins

As part of a program focused on the development of new antineoplastic agents based on scaffolds found in natural products, we explored the isoflavone family as potential enzyme inhibitors. We required biotin-modified isoflavones to identify potential biological targets, and we selected the C-2 position in isoflavones as an attachment site for an alkyl group bearing a terminal carboxylic acid to which we could attach a biotin derivative. The base-catalyzed condensation of 2,4-dihydroxy-substituted deoxybenzoins with cyclic anhydrides mediated by a combination of triethylamine and 1,8-diazabicyclo[5.4.0]undec-7-ene led to an efficient synthesis of the desired 2-(ω-carboxyalkyl)isoflavones with functional groups at C-5, 6 and 7 and with various substituents in the C-3 phenyl group.

TREATMENT OF HOT FLUSHES, VASOMOTOR SYMPTOMS, AND NIGHT SWEATS WITH SEX STEROID PRECURSORS IN COMBINATION WITH SELECTIVE ESTROGEN RECEPTOR MODULATORS

Novel methods for reduction or elimination of the incidence of hot flushes, vasomotor symptoms, and night sweats while decreasing the risk of acquiring breast, uterine or endometrial cancer and furthermore having beneficial effect by inhibiting the develo