3098-38-2

Basic information

• Product Name: 1-(3-ACETYL-2,4-DIHYDROXY-6-METHOXYPHENYL)ETHAN-1-ONE
• Synonyms: 1-(3-ACETYL-2,4-DIHYDROXY-6-METHOXYPHENYL)ETHAN-1-ONE
• CAS NO: 3098-38-2
• Molecular Formula: C₁₁H₁₂O₅
• Molecular Weight: 224.21
• Mol File: 3098-38-2.mol
• Article Data: 1

Chemical Properties

• Melting Point: 255-257 °C(Solv: methanol (67-56-1))
• Boiling Point: 437.2±45.0 °C(Predicted)
• Appearance: /
• Density: 1.293±0.06 g/cm3(Predicted)
• PKA: 7.80±0.28(Predicted)
• CAS DataBase Reference: 1-(3-ACETYL-2,4-DIHYDROXY-6-METHOXYPHENYL)ETHAN-1-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3-ACETYL-2,4-DIHYDROXY-6-METHOXYPHENYL)ETHAN-1-ONE(3098-38-2)
• EPA Substance Registry System: 1-(3-ACETYL-2,4-DIHYDROXY-6-METHOXYPHENYL)ETHAN-1-ONE(3098-38-2)

Safety Data

• Hazardous Substances Data: 3098-38-2(Hazardous Substances Data)

Usage

Preparation

Preparation by reaction of phloroglucinol monomethyl ether, ? with boron trifluoride-acetic acid complex at 100° for 4 h (80%) ; ? with acetic anhydride and acetic acid in the presence of boron trifluoride at 20° for 1 h (81%).

Upstream product

• 186581-53-3 diazomethane 
• 2161-86-6 2,4-diacetylphloroglucinol 
• 2174-64-3 5-methoxyresorcinol 
• 108-24-7 acetic anhydride 
• 412036-66-9 2-acetyl-5-methoxy-4-trichloroacetyl-resorcinol 
• 64-19-7 acetic acid 
• 74-88-4 methyl iodide 
• 108-73-6 3,5-dihydroxyphenol 
• 720698-36-2 2,2,2-trichloro-1-(2,4-dihydroxy-6-methoxy-phenyl)-ethanone 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 3098-69-9 1,1′-(2,4,6-trimethoxy-1,3-phenylene)bis(ethan-1-one) 

Relevant articles and documents

Synthesis, cytotoxicity, anti-oxidative and anti-inflammatory activity of chalcones and influence of A-ring modifications on the pharmacological effect

Besides 2′,4′-dihydroxy-4,6′-dimethoxy-3′-prenylchalcone (1) and 4-acetoxy-2′,4′-dihydroxy-6′-methoxy-3′-prenylchalkon (2), both phase II metabolites of xanthohumol in rats, also a principally new chalcone 3′-coumaroyl-2′,4,4′-trihydroxy-6′-methoxychalcone (3), structurally derived from helichrysetin (4) by introducing a second coumaroyl substructure at C-3′ was synthesized. Furthermore new chalcones were synthesized by combination of the B-Ring fragments of helichrysetin, xanthohumol, xanthohumol C and xanthohumol H with ferulic or caffeic acid moieties in Ring A. Compound 3 showed the highest cytotoxic activity against HeLa cells with an IC50 value of 7.3 ± 0.4 μM. Anti-oxidative effects were determined in the ORAC assay and revealed very strong activity for 3 and 3-methoxyhelichrysetin (6) exhibiting 7.7 ± 0.3 and 6.0 ± 1.3 Trolox equivalents, respectively. The anti-inflammatory activity of all compounds was measured in an in vitro ICAM-1 assay with human microvascular endothelial cells (HMEC-1) and compared with the activity of other structurally related chalcones. The results showed increasing anti-inflammatory activity for the new synthetic chalcones exhibiting a caffeoyl substructure with 3-hydroxyhelichrysetin (5) and 3-hydroxyxanthohumol H (14) being the most active. At 10 μM the TNFα induced expression of ICAM-1 was significantly reduced to 65.8 and 69.6% of control, respectively.