4047-24-9

Basic information

• Product Name: 1-[2-(BENZYLOXY)-6-HYDROXYPHENYL]ETHAN-1-ONE
• Synonyms: 1-[2-(BENZYLOXY)-6-HYDROXYPHENYL]ETHAN-1-ONE;6'-(Benzyloxy)-2'-hydroxyacetophenone;1-[2-Hydroxy-6-(benzyloxy)phenyl]ethanone;Populneol;1-(2-(benzyloxy)-6-hydroxyphenyl)ethanone
• CAS NO: 4047-24-9
• Molecular Formula: C₁₅H₁₄O₃
• Molecular Weight: 242.27
• Mol File: 4047-24-9.mol
• Article Data: 21

Chemical Properties

• Melting Point: 109 °C
• Boiling Point: 392.1°Cat760mmHg
• Flash Point: 146.6°C
• Appearance: /
• Density: 1.187g/cm³
• Vapor Pressure: 1.04E-06mmHg at 25°C
• Refractive Index: 1.594
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 1-[2-(BENZYLOXY)-6-HYDROXYPHENYL]ETHAN-1-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[2-(BENZYLOXY)-6-HYDROXYPHENYL]ETHAN-1-ONE(4047-24-9)
• EPA Substance Registry System: 1-[2-(BENZYLOXY)-6-HYDROXYPHENYL]ETHAN-1-ONE(4047-24-9)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 4047-24-9(Hazardous Substances Data)

Usage

Preparation

Preparation by reaction of benzyl chloride with 2,6-dihydroxyacetophenone, in the presence of potassium carbonate in refluxing acetone; in the presence of potassium carbonate and potassium iodide in refluxing acetone for 18 h (40%); in the presence of 15% aqueous sodium hydroxide, by heating in a water bath(67%).

InChI:InChI=1/C15H14O3/c1-11(16)15-13(17)8-5-9-14(15)18-10-12-6-3-2-4-7-12/h2-9,17H,10H2,1H3

Upstream product

• 100-39-0 benzyl bromide 
• 490-78-8 2,5-Dihydroxyacetophenone 
• 699-83-2 2,6-dihydroxylacetophenone 
• 584-08-7 potassium carbonate 
• 100-44-7 benzyl chloride 

Downstream Products

• 205308-01-6 6'-benzyloxy-2'-(cinnamoyloxy)acetophenone 
• 245726-41-4 2'-benzyloxy-6'-(4-methoxycinnamoyloxy)acetophenone 
• 221195-27-3 1-(6-benzyloxy-2-hydroxyphenyl)-3-hydroxy-11-phenylundecan-1-one 
• 652539-21-4 6'-benzyloxy-2'-(4-benzyloxycinnamoyloxy)acetophenone 
• 652539-24-7 6'-benzyloxy-2'-(3,4-dibenzyloxycinnamoyloxy)acetophenone 
• 86788-63-8 (E)-1-(2-(benzyloxy)-6-hydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one 
• 55788-97-1 5-benzyloxy-4-hydroxy-2H-1-benzopyran-2-one 
• 133839-69-7 1-(2-Benzyloxy-6-hydroxyphenyl)-3-hydroxy-9-(3,4-dimethoxyphenyl)nonan-1-one 
• 133839-68-6 1-(2-Benzyloxy-6-hydroxyphenyl)-3-hydroxy-9-(4-methoxyphenyl)nonan-1-one 
• 133839-70-0 1-(2-Benzyloxy-6-hydroxyphenyl)-3-hydroxy-9-(3,4-methylenedioxyphenyl)nonan-1-one 
• 133839-67-5 1-(2-Benzyloxy-6-hydroxyphenyl)-3-hydroxy-9-phenylnonan-1-one 

Relevant articles and documents

Anti‐melanogenic properties of velutin and its analogs?

Velutin, one of the flavones contained in natural plants, has various beneficial activities, such as skin whitening, as well as anti‐inflammatory, anti‐allergic, antioxidant, and antimicrobial activities. However, the relationship between the structure of velutin and its anti‐melanogenesis activity is not yet investigated. In this study, we obtained 12 velutin derivatives substituted at C5, C7, C3′, and C4′ of the flavone backbone with hydrogen, hydroxyl, and methoxy functionalities by chemical synthesis, to perform SAR analysis of velutin structural analogues. The SAR study revealed that the substitution of functional groups at C5, C7, C3′, and C4′ of the flavone backbone affects biological activities related to melanin synthesis. The coexistence of hydroxyl and methoxy at the C5 and C7 position is essential for inhibiting tyrosinase activity. However, 1,2‐diol compounds substituted at C3′ and C4′ of flavone backbone induce apoptosis of melanoma cells. Further, substitution at C3′ and C4′ with methoxy or hydrogen is essential for inhibiting melanogenesis. Thus, this study would be helpful for the development of natural‐derived functional materials to regulate melanin synthesis.

NOVEL ANALOGUES OF EPICATECHIN AND RELATED POLYPHENOLS

The present invention provides novel analogues of epicatechin and related polyphenols, their variously functionalized derivatives, process for preparation of the same, composition comprising these compounds and their method of use.

Development of flavonoid-based inverse agonists of the key signaling receptor US28 of human cytomegalovirus

A series of 31 chalcone- and flavonoid-based derivatives were synthesized in good overall yields and screened for their inverse agonist activity on the US28 receptor of human cytomegalovirus (HCMV). With one exception (e.g., 2-(5-bromo-2-methoxyphenyl)-3-hydroxy-4H-chromen-4-one), halogen-substituted flavonoids were typically more potent inverse agonists than their related hydro derivatives. While toxicity could be used to partially explain the inverse agonist activity of some members of the series, 5-(benzyloxy)-2-(5-bromo-2- methoxyphenyl)-4H-chromen-4-one (11b) acted on the US28 receptor as a nontoxic, inverse agonist. The full inverse agonism (efficacy, -89%) and potency (EC 50 = 3.5 μM) observed with flavonoid 11b is especially important as it provides both a new tool to study US28 signaling and a potential platform for the future development of HCMV-targeting drugs.