1818-27-5

Basic information

• Product Name: 1-(2,4,5-Trihydroxyphenyl)ethanone
• Synonyms: 1-(2,4,5-Trihydroxyphenyl)ethanone
• CAS NO: 1818-27-5
• Molecular Formula: C₈H₈O₄
• Molecular Weight: 168.14672
• Mol File: 1818-27-5.mol
• Article Data: 8

Chemical Properties

• Melting Point: 200-202 °C
• Boiling Point: 404.3°Cat760mmHg
• Flash Point: 212.4°C
• Appearance: /
• Density: 1.446g/cm³
• Vapor Pressure: 4.1E-07mmHg at 25°C
• Refractive Index: 1.64
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 7.81±0.23(Predicted)
• CAS DataBase Reference: 1-(2,4,5-Trihydroxyphenyl)ethanone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2,4,5-Trihydroxyphenyl)ethanone(1818-27-5)
• EPA Substance Registry System: 1-(2,4,5-Trihydroxyphenyl)ethanone(1818-27-5)

Safety Data

• Hazardous Substances Data: 1818-27-5(Hazardous Substances Data)

Usage

Preparation

Preparation by Fries rearrangement of 1,2,4-triacetoxy-benzene,with aluminium chloride in nitrobenzene (30–43%)with zinc chloride at 135–140° (49–53%)with p-toluenesulfonic acid in refluxing tetrachloroethane or benzene or without solvent at 135–140° (60%).

InChI:InChI=1/C8H8O4/c1-4(9)5-2-7(11)8(12)3-6(5)10/h2-3,10-12H,1H3

Upstream product

• 66003-50-7 1-<4,5-(methylenedioxy)-2-hydroxyphenyl>ethanone 
• 533-31-3 Sesamol 
• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 4460-86-0 asaraldehyde 
• 1818-28-6 2',4',5'-trimethoxyacetophenone 
• 7446-70-0 aluminium trichloride 
• 613-03-6 1,2,4-triacetoxybenzene 
• 64-19-7 acetic acid 
• 533-73-3 1,2,4-Trihydroxybenzene 
• 75-05-8 acetonitrile 
• 108-24-7 acetic anhydride 
• 106-51-4 p-benzoquinone 

Downstream Products

• 55939-28-1 4-Methyl-6,7-diacetoxycoumarin 
• 20628-06-2 2-hydroxy-4,5-dimethoxyacetophenone 
• 66003-50-7 1-<4,5-(methylenedioxy)-2-hydroxyphenyl>ethanone 
• 7298-38-6 2',4',5'-tribenzyloxyacetophenone 
• 22089-12-9 2,5-dihydroxy-4-methoxyacetophenone 
• 7298-39-7 4',5'-bis(benzyloxy)-2'-hydroxyacetophenone 
• 34176-17-5 1-(4-(benzyloxy)-2,5-dihydroxyphenyl)ethan-1-one 
• 52249-88-4 1-(5-(benzyloxy)-2-hydroxy-4-methoxyphenyl)ethan-1-one 
• 42059-51-8 [4,5-bis(acetyloxy)-2-hydroxyphenyl]ethanone 
• 85288-45-5 2'-hydroxy-3,4,4',5'-tetramethoxy-trans-chalcone 

Relevant articles and documents

Iron-catalyzed arene C-H hydroxylation

The sustainable, undirected, and selective catalytic hydroxylation of arenes remains an ongoing research challenge because of the relative inertness of aryl carbon-hydrogen bonds, the higher reactivity of the phenolic products leading to over-oxidized by-products, and the frequently insufficient regioselectivity. We report that iron coordinated by a bioinspired L-cystine-derived ligand can catalyze undirected arene carbon-hydrogen hydroxylation with hydrogen peroxide as the terminal oxidant. The reaction is distinguished by its broad substrate scope, excellent selectivity, and good yields, and it showcases compatibility with oxidation-sensitive functional groups, such as alcohols, polyphenols, aldehydes, and even a boronic acid. This method is well suited for the synthesis of polyphenols through multiple carbon-hydrogen hydroxylations, as well as the late-stage functionalization of natural products and drug molecules.

2-OXO-5H-CHROMENO[4,3-B]PYRIDINES FOR USE IN THE TREATMENT OF HEPATITIS B

The present invention discloses compounds according to Formula (I), wherein R1, R2a, R2b, R3, R4, and R5 are as defined herein. The present invention relates to compounds, methods for their production, pharmaceutical compositions comprising the same, and methods of treatment using the same, for the prophylaxis and/or treatment of diseases involving hepatitis B by administering the compound of the invention.

Antimalarial activity of HIV-1 protease inhibitor in chromone series

Increasing parasite resistance to nearly all available antimalarial drugs becomes a serious problem to human health and necessitates the need to continue the search for new effective drugs. Recent studies have shown that clinically utilized HIV-1 protease (HIV-1 PR) inhibitors can inhibit the in vitro and in vivo growth of Plasmodium falciparum. In this study, a series of chromone derivatives possessing HIV-1 PR inhibitory activity has been tested for antimalarial activity against P. falciparum (K1 multi-drug resistant strain). Chromone 15, the potent HIV-1 PR inhibitor (IC50 = 0.65 μM), was found to be the most potent antimalarial compound with IC50 = 0.95 μM while primaquine and tafenoquine showed IC50 = 2.41 and 1.95 μM, respectively. Molecular docking study of chromone compounds against plasmepsin II, an aspartic protease enzyme important in hemoglobin degradation, revealed that chromone 15 exhibited the higher binding affinity (binding energy = -13.24 kcal/mol) than the known PM II inhibitors. Thus, HIV-1 PR inhibitor in chromone series has the potential to be a new class of antimalarial agent.