789-80-0

Basic information

• Product Name: 1-(2,5-dihydroxy-4-methoxyphenyl)-2-phenylethanone
• Synonyms: 1-(2,5-dihydroxy-4-methoxyphenyl)-2-phenylethanone
• CAS NO: 789-80-0
• Molecular Weight: 258.274
• Mol File: 789-80-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1-(2,5-dihydroxy-4-methoxyphenyl)-2-phenylethanone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2,5-dihydroxy-4-methoxyphenyl)-2-phenylethanone(789-80-0)
• EPA Substance Registry System: 1-(2,5-dihydroxy-4-methoxyphenyl)-2-phenylethanone(789-80-0)

Safety Data

• Hazardous Substances Data: 789-80-0(Hazardous Substances Data)

Upstream product

• 103-82-2 phenylacetic acid 
• 824-46-4 methoxyhydroquinone 
• 18439-96-8 1-(2-hydroxy-4-methoxyphenyl)-2-phenylethanone 

Downstream Products

• 54921-43-6 6-hydroxy-7-methoxy-isoflavone 
• 115214-36-3 6-[(2,4-dinitro-phenylhydrazono)-methyl]-6-hydroxy-7-methoxy-2-methyl-3-phenyl-chromen-4-one 
• 14291-45-3 5,6,7-trimethoxy-2-methyl-3-phenyl-chromen-4-one 
• 109598-97-2 5,6-dihydroxy-7-methoxy-2-methyl-3-phenyl-chromen-4-one 
• 131977-22-5 6-hydroxy-7-methoxy-2-methyl-4-oxo-3-phenyl-4H-chromene-5-carbaldehyde 
• 855296-21-8 5,6,7-trihydroxy-2-methyl-3-phenyl-chromen-4-one 
• 1092-26-8 6-hydroxy-7-methoxy-2-methyl-3-phenyl-chromen-4-one 
• 24195-31-1 1-(2-hydroxy-4,5-dimethoxy-phenyl)-2-phenylethanone 
• 800-71-5 6-acetoxy-7-methoxy-2-methyl-3-phenyl-chromen-4-one 

Relevant articles and documents

Synthesis and structure-activity relationship study of deoxybenzoins on relaxing effects of porcine coronary artery

Deoxybenzoins are potent antioxidants and tyrosinase inhibitors with potential to be developed as food preservatives and cosmetic ingredients. To explore the potential in cardiovascular protection, 25 polyphenolic deoxybenzoins were synthesized and evaluated for inhibitory effects on KCl-induced porcine coronary arterial contraction. The results revealed deoxybenzoins are significant inhibitors of KCl-induced arterial contraction. Among those synthesized, two-thirds of the deoxybenzoins exhibited moderate to good efficacy on relaxing contracted artery including 2,4-dihydroxydeoxybenzoin with EC50 = 3.30 μM (Emax = 100%, n = 7) and 2,4-dihydroxy-4′-methoxydeoxybenzoin EC50 = 3.70 μM (E max = 100%, n = 5). Deoxybenzoins displayed an endothelium-dependent relaxing manner on the contracted artery; the contractile responses of neither endothelium denuded nor L-NAME deactivated rings were inhibited. The structure-activity relationships of deoxybenzoin on arterial relaxing effects concluded that the 2,4-dihydroxylated deoxybenzoins presented a potential vascular relaxing pharmacophore, with favoring substitution on ring B in the order of H ≤ p-OMe > p-OH > o-OMe > m,p-diOMe ≤ m-OMe.

Synthesis of various kinds of isoflavones, isoflavanes, and biphenyl- ketones and their 1,1-diphenyl-2-picrylhydrazyl radical-scavenging activities

Forty-eight kinds of isoflavones (8), thirty-one isoflavanes (9), and forty-seven biphenyl-ketones (10, 10') were synthesized from eleven kinds of substituted phenols (11) and six phenylacetic acids (12). Among them, seventy-five compounds are new. The radical scavenging activities of these compounds were evaluated using 1,1- diphenyl-2-picrylhydrazyl (DPPH) at pH 6.0. We found that thirty-nine out of forty-three compounds having a catechol moiety on either the A- or the B-ring exhibited a high activity (ED50=12-54 μM) similar to that of catechin. In these cases, the remaining part of their structure seemed to have little effect on their activity. Many 6- or 8-hydroxyisoflavanes (9E-I) and their biphenyl-ketone derivatives (10E-H) also showed a high activity (ED50=50=26-32 μM). This study suggests that natural isoflavones have the possibilities of exhibiting antioxidant activities through the hydroxylation at the C6-, C8-, or C3'-position or the formation of the isoflavanes (9) and/or the biphenyl-ketone derivatives (10') by metabolism or biotransformation.