3602-54-8

Basic information

• Product Name: 1-(2,4-DIHYDROXY-6-METHOXY-PHENYL)-ETHANONE
• Synonyms: 1-(2,4-DIHYDROXY-6-METHOXY-PHENYL)-ETHANONE;2,4-Dihydroxy-6-methoxyacetophene;2,4-Dihydroxy-6-Methoxyacetophenone;2-O-Methylphloroacetophenone;6-O-Methylphloroacetophenone
• CAS NO: 3602-54-8
• Molecular Formula: C₉H₁₀O₄
• Molecular Weight: 182.1733
• Mol File: 3602-54-8.mol
• Article Data: 25

Chemical Properties

• Melting Point: 139-140 °C
• Boiling Point: 333.493 °C at 760 mmHg
• Flash Point: 135.5℃
• Appearance: /
• Density: 1.284
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.573
• Storage Temp.: 2-8°C
• PKA: 7.60±0.23(Predicted)
• CAS DataBase Reference: 1-(2,4-DIHYDROXY-6-METHOXY-PHENYL)-ETHANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2,4-DIHYDROXY-6-METHOXY-PHENYL)-ETHANONE(3602-54-8)
• EPA Substance Registry System: 1-(2,4-DIHYDROXY-6-METHOXY-PHENYL)-ETHANONE(3602-54-8)

Safety Data

• Hazardous Substances Data: 3602-54-8(Hazardous Substances Data)

Usage

Uses

2,4-Dihydroxy-6-methoxyacetophenone is a reagent that is used in the preparation of polysubstituted synthetic chalcones.

Preparation

Preparation by reaction of acetonitrile on phloroglucinol monomethyl ether (Hoesch reaction).

InChI:InChI=1/C9H10O4/c1-5(10)9-7(12)3-6(11)4-8(9)13-2/h3-4,11-12H,1-2H3

Upstream product

• 480-66-0 2,4,6-trihydroxyacetophenone 
• 832-58-6 1-(2,4,6-trimethoxyphenyl)ethanone 
• 90-24-4 2-hydroxy-4,6-dimethoxyacetophenone 
• 77-78-1 dimethyl sulfate 
• 186581-53-3 diazomethane 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 1393809-20-5 4-acetyl-5-methoxy-1,3-phenylene bis(4-methylbenzenesulfonate) 
• 65490-09-7 2'-hydroxy-4',6'-bis(methoxymethoxy)acetophenone 
• 404597-94-0 1-(2-methoxy-4,6-bis(methoxymethoxy)phenyl)ethan-1-one 
• 108-73-6 3,5-dihydroxyphenol 
• 249278-28-2 2,4,6-trihydroxyacetophenone monohydrate 
• 18065-05-9 1-[2,4-bis(benzyloxy)-6-hydroxyphenyl]ethanone 
• 621-23-8 1,2,3-trimethoxybenzene 
• 61775-18-6 6-O-methylphloroacetophenone-4-O-<β-D-glucopyranoside> 

Downstream Products

• 83436-29-7 2-Ethyl-phloroglucin-1-monomethylether 
• 480-40-0 5,7-dihydroxy-2-phenyl-chromen-4-one 
• 101161-94-8 4,6-dihydroxy-2-methoxy-5-diphenylmethylacetophenone 
• 101161-95-9 4,6-dihydroxy-2-methoxy-3-diphenylmethylacetophenone 
• 101161-93-7 4,6-dihydroxy-2-methoxy-3,5-bis(diphenylmethyl)acetophenone 
• 27364-68-7 6-Acetyl-3,4-dihydro-7-hydroxy-5-methoxy-2,2-dimethyl-2H-1-benzopyran 
• 32550-59-7 6-Acetyl-5-hydroxy-7-methoxy-3,4-dihydro-2,2-dimethyl-2H<1>benzopyran 
• 158017-91-5 4-ethoxymethoxy-2-hydroxy-6-methoxy-acetophenone 
• 404597-94-0 1-(2-methoxy-4,6-bis(methoxymethoxy)phenyl)ethan-1-one 
• 25983-76-0 isoevodionol 
• 1447-88-7 hispidulin 
• 25892-95-9 1-(4-(benzyloxy)-6-hydroxy-2,3-dimethoxyphenyl)ethan-1-one 
• 25892-94-8 1-(4-(benzyloxy)-3,6-dihydroxy-2-methoxyphenyl)ethan-1-one 
• 74047-37-3 1-(4-allyloxy-2-hydroxyl-6-methoxyphenyl)ethanone 

Relevant articles and documents

KNIPHOLONE: A UNIQUE ANTHRQUINONE DERIVATIVE FROM KNIPHOFIA FOLIOSA

The roots of Kniphofia foliosa afforded, in addition to chrysophanol, a novel anthraquinone named knipholone, whose structure was determined by spectroscopic methods as well as by degradation to known compounds.Key Word Index - Kniphofia foliosa; Liliaceae; anthraquinone; chrysophanol; knipholone.

Effects of substituent pattern on the intracellular target of antiproliferative benzo[b]thiophenyl chromone derivatives

A new biological scaffold was produced by replacing the 6π-electron phenyl ring-B of a natural flavone skeleton with a 10π-electron benzothiophene (BT). Since aromatic rings are important for ligand protein interactions, this expansion of the π-electron system of ring-B might change the bioactivity profile. One of the resulting novel natural product-inspired compounds, 2-(benzo[b]thiophen-3-yl)-5-hydroxy-7-isopropoxy-6-methoxyflavone (6), effectively arrested the cell cycle at the G2/M phase and displayed significant antiproliferative effects with IC50 values of 0.05–0.08 μM against multiple human tumor cell lines, including a multidrug resistant line. A structure-activity relationship study revealed that a 10π-electron system with high aromaticity, juxtaposed 4-oxo and 5-hydroxy groups, and 7-alkoxy groups were important for potent antimitotic activity. Interestingly, two BT-flavonols (3-hydroxyflavone), 16 and 20, with 3-hydroxy and 5-alkoxy groups, induced distinct biological profiles affecting the cell cycle at the G1/S phase by inhibition of DNA replication through an interaction with topoisomerase I.

Annphenone, a phenolic acetophenone from Artemisia annua

Fractionation of the n-butanol extract of Artemisia annua led to the isolation of a new phenolic acetophenone, the structure of which was elucidated as 2,4-dihydroxy-6-methoxy-acetophenone 40-O-β-D-glucopyranoside on the basis of spectroscopic data.

Construction and Biological Evaluation of Small Libraries Based on the Intermediates within the Total Synthesis of Uvaretin

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Biocatalytic Friedel–Crafts Acylation and Fries Reaction

The Friedel–Crafts acylation is commonly used for the synthesis of aryl ketones, and a biocatalytic version, which may benefit from the chemo- and regioselectivity of enzymes, has not yet been introduced. Described here is a bacterial acyltransferase which can catalyze Friedel–Crafts C-acylation of phenolic substrates in buffer without the need of CoA-activated reagents. Conversions reach up to >99 %, and various C- or O-acyl donors, such as DAPG or isopropenyl acetate, are accepted by this enzyme. Furthermore the enzyme enables a Fries rearrangement-like reaction of resorcinol derivatives. These findings open an avenue for the development of alternative and selective C?C bond formation methods.