92549-46-7

Basic information

• Product Name: 1-(2,4-DIHYDROXYPHENYL)-2-(2-METHOXYPHENYL)ETHAN-1-ONE
• Synonyms: AURORA 15344;1-(2,4-Dihydroxyphenyl)-2-(2-methoxyphenyl)ethanone;1-(2,4-DIHYDROXYPHENYL)-2-(2-METHOXYPHENYL)ETHAN-1-ONE
• CAS NO: 92549-46-7
• Molecular Formula: C₁₅H₁₄O₄
• Molecular Weight: 258.27
• Mol File: 92549-46-7.mol
• Article Data: 7

Chemical Properties

• Melting Point: 164°C
• Appearance: /
• CAS DataBase Reference: 1-(2,4-DIHYDROXYPHENYL)-2-(2-METHOXYPHENYL)ETHAN-1-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2,4-DIHYDROXYPHENYL)-2-(2-METHOXYPHENYL)ETHAN-1-ONE(92549-46-7)
• EPA Substance Registry System: 1-(2,4-DIHYDROXYPHENYL)-2-(2-METHOXYPHENYL)ETHAN-1-ONE(92549-46-7)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 92549-46-7(Hazardous Substances Data)

Usage

Preparation

Preparation by reaction of o-methoxyphenylacetic acid with resorcinol in the presence of boron trifluoride etherate under argon on a water bath for 1 h (98%).

Upstream product

• 7035-03-2 2-methoxy-benzeneacetonitrile 
• 108-46-3 recorcinol 
• 93-25-4 2-methoxyphenylacetic acid 

Downstream Products

• 18440-00-1 2-Hydroxy-4-methoxyphenyl 2-methoxybenzyl ketone 
• 63909-40-0 7-hydroxy-3-(2-methoxyphenyl)-4H-chromen-4-one 
• 142751-37-9 Dimethyl-thiocarbamic acid O-{3-hydroxy-4-[2-(2-methoxy-phenyl)-acetyl]-phenyl} ester 
• 323575-75-3 2-ethyl-7-hydroxy-3-(2-methoxyphenyl)chromen-4-one 
• 610758-63-9 7-hydroxy-3-(2-methoxy-phenyl)-4-oxo-4H-chromene-2-carboxylic acid ethyl ester 
• 303119-53-1 7-hydroxy-3-(2-methoxyphenyl)-2-trifluoromethyl-4H-chromen-4-one 
• 1081127-17-4 C₁₅H₁₃NO₃ 
• 6468-49-1 3-hydroxy-6H-benzofuro[3,2-c]chromen-6-one 
• 19725-36-1 7-hydroxy-3-(2-hydroxyphenyl)-4H-chromen-4-one 
• 1614253-83-6 9-(2-methoxyphenylacetyl)-7,10-dihydroxy-7H-benzo[5,6]-pyrano[3,2-c]chromen-6-one 
• 308087-55-0 7-hydroxy-3-(2-methoxy-phenyl)-2-methyl-chromen-4-one 
• 855627-28-0 7-acetoxy-3-(2-acetoxy-phenyl)-2-methyl-chromen-4-one 
• 97405-81-7 2-bromomethyl-7-hydroxy-3-(2-hydroxy-phenyl)-chromen-4-one 
• 97575-50-3 7-hydroxy-2-hydroxymethyl-3-(2-hydroxy-phenyl)-chromen-4-one 

Relevant articles and documents

Enantioselective Synthesis of Isoflavanones and Pterocarpans through a RuII-Catalyzed ATH-DKR of Isoflavones

Noyori-Ikariya RuII complexes promoted the one-pot C=C/C=O bonds reduction of isoflavones using sodium formate as the hydrogen source through Asymmetric Transfer Hydrogenation-Dynamic Kinetic Resolution (ATH-DKR). Due to the neutral conditions employed, isoflavones with different substituents at the 2’-position of B-ring (H, OH, OMe and Br) were successfully reduced. Ten cis-3-phenylchroman-4-ols were selectively obtained (>20 : 1 dr) in good yields (up to 86 %) and excellent enantioselectivities (up to >99 : 1 er). The synthetic applications of these chiral compounds were also demonstrated. Enantioenriched isoflavanones were obtained under mild metal-free oxidation of the cis-3-phenylchroman-4-ols while pterocarpans were synthesized by two strategies: an acid-catalyzed cyclization and a novel approach based on a Pd-catalyzed C?O intramolecular cross-coupling reaction.

Development of 3-alkyl-6-methoxy-7-hydroxy-chromones (AMHCs) from natural isoflavones, a new class of fluorescent scaffolds for biological imaging

Starting from 7-hydroxyisoflavones, we developed a new class of fluorescent scaffolds, 3-alkyl-6-methoxy-7-hydroxy-chromones (AMHCs, MW ～ 205.19, λab ～ 350 nm, λem ～ 450 nm) via a trial and error process. AMHCs have the advantages of being a small molecular moiety, having strong fluorescence in basic buffers, reasonable solubility and stability, non-toxicity, and are conveniently linked to pharmacophores. AMHCs were successfully used in fluorescence microscopy imaging of cells and tissues. This journal is

Synthesis, optical resolution, absolute configuration, and osteogenic activity of cis-pterocarpans

A convenient synthesis of natural and synthetic pterocarpans was achieved in three steps. Optical resolution of the respective enantiomers was accomplished by analytical and semi-preparative HPLC on a chiral stationary phase. For medicarpin and its synthetic derivative 9-demethoxymedicarpin, the absolute configuration was confirmed by a combination of experimental LC-ECD coupling and quantum-chemical ECD calculations. (-)-Medicarpin and (-)-9-demethoxymedicarpin are both 6aR,11aR-configured, and consequently the corresponding enantiomers, (+)-medicarpin and (+)-9-demethoxymedicarpin, possess the 6aS,11aS-configuration. A comparative mechanism study for osteogenic (bone forming) activity of medicarpin (racemic versus enantiomerically pure material) revealed that (+)-(6aS,11aS)-medicarpin (6a) significantly increased the bone morphogenetic protein-2 (BMP2) expression and the level of the bone-specific transcription factor Runx-2 mRNA, while the effect was opposite for the other enantiomer, (-)-(6aR,11aR)-medicarpin (6a), and for the racemate, (±)-medicarpin, the combined effect of both the enantiomers on transcription levels was observed. The Royal Society of Chemistry 2012.