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

Used in Pharmaceutical Industry:
1-(2,4-DIHYDROXY-6-METHOXY-PHENYL)-ETHANONE is used as a reagent for the preparation of polysubstituted synthetic chalcones. Chalcones are a class of organic compounds that have been extensively studied for their diverse range of biological activities, including anti-inflammatory, antioxidant, and anticancer properties. The synthesis of these chalcones using 2,4-Dihydroxy-6-methoxyacetophenone as a reagent can lead to the development of novel therapeutic agents with potential applications in the treatment of various diseases.
Used in Chemical Synthesis:
1-(2,4-DIHYDROXY-6-METHOXY-PHENYL)-ETHANONE is used as an intermediate in the synthesis of various organic compounds. Its unique structure allows for further functionalization and modification, making it a valuable building block in the preparation of complex molecules. 1-(2,4-DIHYDROXY-6-METHOXY-PHENYL)-ETHANONE can be utilized in the synthesis of a wide range of products, including pharmaceuticals, agrochemicals, dyes, and other specialty chemicals.
Used in Research and Development:
1-(2,4-DIHYDROXY-6-METHOXY-PHENYL)-ETHANONE is also used in research and development for the exploration of new chemical reactions and synthetic pathways. Its reactivity and structural features make it an attractive candidate for studying novel reaction mechanisms and developing innovative synthetic strategies. 1-(2,4-DIHYDROXY-6-METHOXY-PHENYL)-ETHANONE can be employed in academic and industrial research settings to advance the understanding of organic chemistry and contribute to the discovery of new chemical entities with potential applications in various fields.

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

• 832-58-6 1-(2,4,6-trimethoxyphenyl)ethanone 
• 90-24-4 2-hydroxy-4,6-dimethoxyacetophenone 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 77-78-1 dimethyl sulfate 
• 1393809-20-5 4-acetyl-5-methoxy-1,3-phenylene bis(4-methylbenzenesulfonate) 
• 108-73-6 3,5-dihydroxyphenol 
• 65490-09-7 2'-hydroxy-4',6'-bis(methoxymethoxy)acetophenone 
• 404597-94-0 1-(2-methoxy-4,6-bis(methoxymethoxy)phenyl)ethan-1-one 
• 108-22-5 Isopropenyl acetate 
• 2174-64-3 5-methoxyresorcinol 
• 2466-76-4 N-Acetylimidazole 
• 249278-28-2 2,4,6-trihydroxyacetophenone monohydrate 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 18065-05-9 1-[2,4-bis(benzyloxy)-6-hydroxyphenyl]ethanone 

Downstream Products

• 480-40-0 5,7-dihydroxy-2-phenyl-chromen-4-one 
• 25983-76-0 isoevodionol 
• 39548-89-5 1-(4-(benzyloxy)-2-hydroxy-6-methoxyphenyl)ethan-1-one 
• 404597-94-0 1-(2-methoxy-4,6-bis(methoxymethoxy)phenyl)ethan-1-one 
• 60715-04-0 1-[5-hydroxy-7-methoxy-2-methyl-2-(4-methyl-3-pentenyl)-2H-chromen-6-yl]ethanone 
• 1393809-15-8 (+/-)-3-hydroxy-1-(5-hydroxy-7-methoxy-2,2-dimethyl-2H-chromen-6-yl)-3-p-tolylpropan-1-one 
• 1393809-16-9 (+/-)-3-hydroxy-1-(5-hydroxy-7-methoxy-2,2-dimethyl-2H-chromen-6-yl)-3-p-tolylpropan-1-one 
• 1393809-17-0 (+/-)-3-hydroxy-1-(5-hydroxy-7-methoxy-2,2-dimethyl-2H-chromen-6-yl)-3-(4-methoxyphenyl)propan-1-one 
• 1393809-18-1 (+/-)-3-(3,4-dimethoxyphenyl)-3-hydroxy-1-(5-hydroxy-7-methoxy-2,2-dimethyl-2H-chromen-6-yl)propan-1-one 
• 1393809-19-2 (+/-)-3-(3,5-dimethoxyphenyl)-3-hydroxy-1-(5-hydroxy-7-methoxy-2,2-dimethyl-2H-chromen-6-yl)propan-1-one 
• 51703-76-5 obovatachalcone 
• 1393809-14-7 (+/-)-elatadihydrochalcone 
• 855740-21-5 2′,4′-dihydroxy-4,6′-dimethoxychalcone 
• 75679-58-2 2’,4’-dihydroxy-4,6’-dimethoxydihydrochalcone 

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.

Bulbine-knipholone, a new, axially chiral phenylanthraquinone from Bulbine abyssinica (Asphodelaceae): Isolation, structural elucidation, synthesis, and antiplasmodial activity

A new natural phenylanthraquinone, bulbine-knipholone (6), has been isolated from the African plant species Bulbine abyssinica (Asphodelaceae). Its structure was determined by spectroscopic and degradative methods. With the aid of the "lactone concept", an atropo-enantioselective total synthesis has been elaborated, confirming the full absolute structure. Bulbine-knipholone exhibits antiplasmodial activity. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

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.

AN ANTHRONE, AN ANTHRAQUINONE AND TWO OXANTHRONES FROM KNIPHOFIA FOLIOSA

The compounds isoknipholone, isoknipholone anthrone, foliosone and isofoliosone were isolated from the stem of Kniphofia foliosa and their structures determined by spectral analyses.In addition, the known compounds, aloesaponol III, aloesaponol III-8-methyl ether and 4,6-dihydroxy-2-methoxyacetophenone were isolated and identified. - Key words: Kniphofia foliosa; Asphodelaceae; stem; anthrone; anthraquinone; oxanthrones; isoknipholone anthrone; isoknipholone; foliosone; isofoliosone.

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.

Neuroregenerative Potential of Prenyl- And Pyranochalcones: A Structure-Activity Study

Loss of neuronal tissue is a hallmark of age-related neurodegenerative diseases. Since adult neurogenesis has been confirmed in the human brain, great interest has arisen in substances stimulating the endogenous neuronal regeneration mechanism based on ad

Design, synthesis and biological evaluation of dimethyl cardamonin (DMC) derivatives as P-glycoprotein-mediated multidrug resistance reversal agents

Background: P-glycoprotein (P-gp) has been regarded as an important factor in the multidrug resistance (MDR) of tumor cells within the last decade, which can be solved by inhibiting P-gp to reverse MDR. Thus, it is an effective strategy to develop inhibitor of P-gp. Objective: In this study, the synthesis of a series of derivatives had been carried out by bioisosterism design on the basis of Dimethyl Cardamonin (DMC). Subsequently, we evaluated their reversal activities as potential P-glycoprotein (P-gp)-mediated Multidrug Resistance (MDR) agents. Methods: Dimethyl cardamonin derivatives were synthesized from acetophenones and the corresponding benzaldehydes in the presence of 40% KOH by Claisen-Schmidt reaction. Their cytotoxicity and reversal activities in vitro were assessed with MTT. Moreover, the compound B4 was evaluated by Doxorubicin (DOX) accumulation, Western blot and wound-healing assays deeply. Results and Discussion: The results showed that compounds B2, B4 and B6 had the potency of MDR reversers with little intrinsic cytotoxicity. Meanwhile, these compounds also demonstrated the capability to inhibit MCF-7 and MCF-7/DOX cells migration. Besides, the most compound B4 was selected for further study, which promoted the accumulation of DOX in MCF-7/DOX cells and inhibited the expressionof P-gp at protein levels. Conclusion: The above findings may provide new insights for the research and development of P-gp-mediated MDR reversal agents.

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.

Acyl Donors and Additives for the Biocatalytic Friedel–Crafts Acylation

The Friedel–Crafts acylation is a broadly applied reaction that can be conducted using various types of catalyst. However, a biocatalytic alternative has only been reported recently. In this study, the scope of acetyl donors is described, showing that, in addition to vinyl acetate derivatives, phenyl esters are also suitable donors. Furthermore, it was found that various amines enhance the reaction, whereby the effect do not seem to be correlated to the pH but to the structure of the donor. For instance, 1,4-diazabicyclo[2.2.2]octane (DABCO) turned out to be a viable alternative to imidazole; however the former performed best at pH 9.85, whereas the latter performed best at pH 8.3.

Mallotojaponins B and C: Total Synthesis, Antiparasitic Evaluation, and Preliminary SAR Studies

(Chemical Equation Presented). The first total syntheses of mallotojaponin B and C as well as several analogues have been achieved. Biological evaluation of the synthesized compounds against Plasmodium falciparum and Trypanosoma brucei have also been carried out.