104236-79-5

Basic information

• Product Name: 2-Propen-1-one, 1-(2,4-dihydroxyphenyl)-3-(3-hydroxy-4-methoxyphenyl)-, (E)-
• CAS NO: 104236-79-5
• Molecular Formula: C16H14O5
• Molecular Weight: 286.284
• Mol File: 104236-79-5.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 2-Propen-1-one, 1-(2,4-dihydroxyphenyl)-3-(3-hydroxy-4-methoxyphenyl)-, (E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propen-1-one, 1-(2,4-dihydroxyphenyl)-3-(3-hydroxy-4-methoxyphenyl)-, (E)-(104236-79-5)
• EPA Substance Registry System: 2-Propen-1-one, 1-(2,4-dihydroxyphenyl)-3-(3-hydroxy-4-methoxyphenyl)-, (E)-(104236-79-5)

Safety Data

• Hazardous Substances Data: 104236-79-5(Hazardous Substances Data)

Upstream product

• 621-59-0 isovanillin 
• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 121-33-5 vanillin 
• 5460-32-2 1-iodo-3,4-dimethoxybenzene 
• 67756-04-1 1-(2,4-dimethoxy-phenyl)-prop-2-en-1-one 
• 100753-43-3 (E)-1-(2,4-dimethoxyphenyl)-3-(3,4-dimethoxyphenyl)prop-2-en-1-one 

Downstream Products

• 66281-59-2 2,3-dihydroxy-4-(carboxymethoxy)-4'-methoxychalcone 
• 50297-25-1 2,3'-dihydroxy-4-(carbethoxymethoxy)-4'-methoxychalcone 
• 54867-60-6 7-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-benzo(b)pyran-4-one 
• 76426-28-3 7-hydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one 
• 2150-11-0 3',4',7-trihydroxyflavone 

Relevant articles and documents

Differential effects of synthesized 2′-oxygenated chalcone derivatives: Modulation of human cell cycle phase distribution

Ten structurally related 2′-oxygenated chalcone derivatives, bearing either hydroxy and/or methoxy substituents on the A and B rings, were synthesized through Claisen-Schmidt condensation. The synthesis procedure was relatively easy and had an acceptable yield. The in vitro cytotoxicities of these compounds against the human tumor cells such as Jurkat, U937 cells, and normal cells PHA stimulated PBMCs were investigated. Among those, compounds 1 (IC50=2.5μM), 2 (1.7μM), and 8 (3.2μM) showed potent inhibitory activity toward Jurkat cell line. In parallel, compounds 1 (6.7μM), 2 (1.5μM), and 10 (5.3μM) showed the highest activity against U937 cell line. However, the chalcones also inhibit the PHA stimulated PBMCs cells, but the IC50 values were relatively high when compared to the tumor cell line values. Studies were also on the effect of synthesized chalcones on the cell cycle phase distribution. In Jurkat cell line, compounds 7 and 9 showed the highest activity and the most striking effect in reduction of the percentage of cells in the S phase, which was associated with an increase of cells in G2/M phase. In U937 cell line, compound 3 increased the proportion of cells in the G0/G1 phase and reduced the proportion in S phase. In contrast, compounds 1, 9, and 10 showed a decrease effect on the percentage of cells in S phase and an increase effect on the percentage of cells in the G2/M phase of the cell cycle. Whereas in the case of PHA stimulated PBMCs, compounds 1, 4, 8, and 10 increased the percentage of cells in G2/M phase, which was associated with a decrease effect in the S phase of the cell cycle.

Synthesis and evaluation of butein derivatives for in vitro and in vivo inflammatory response suppression in lymphedema

Herein, we demonstrate that butein (1) can prevent swelling in a murine lymphedema model by suppressing tumor necrosis factor α (TNF-α) production. Butein derivatives were synthesized and evaluated to identify compounds with in vitro anti-inflammatory activity. Among them, 20 μM of compounds 7j, 7m, and 14a showed 50percent suppression of TNF-α production in mouse peritoneal macrophages after lipopolysaccharide stimulation. Compound 14a, exhibited the strongest potency with an in vitro IC50 of 14.6 μM and suppressed limb volume by 70percent in a murine lymphedema model. The prodrug strategy enabled a six-fold increase in kinetic solubility of compound 1 and five-fold higher levels of active metabolite in the blood for compound 14a via oral administration in the pharmacokinetics study. We suggest that the compound 14a could be developed as a potential therapeutic agent targeting anti-inflammatory activity to alleviate lymphedema progression.

Cytotoxic and antimicrobial activities of some synthetic flavones

Several flavones have been synthesized and their biocidal activity investigated along with their corresponding chalcones against some bacterial and fungal strains as well as brine shrimp nauplii. Compounds 13 and 14 show good antibacterial, antifungal and