832-58-6

Basic information

• Product Name: 2',4',6'-TRIMETHOXYACETOPHENONE
• Synonyms: PHLOROACETOPHENONE TRIMETHYL ETHER;TIMTEC-BB SBB005891;2',4',6'-TRIMETHOXYACETOPHENONE;2,4,6-TRIMETHOXYACETOPHENONE;Phloracetophenone trimethyl ether;O-Methylxanthoxylin;2',4',6'-Trimethoxyacetophenone 97%;1-(2,4,6-Trimethoxyphenyl)ethanone
• CAS NO: 832-58-6
• Molecular Formula: C₁₁H₁₄O₄
• Molecular Weight: 210.23
• Product Categories: Aromatic Acetophenones & Derivatives (substituted);C11 to C12;Carbonyl Compounds;Ketones
• Mol File: 832-58-6.mol
• Article Data: 38

Chemical Properties

• Melting Point: 98-102 °C(lit.)
• Boiling Point: 343 °C at 760 mmHg
• Flash Point: 152 °C
• Appearance: /
• Density: 1.089 g/cm³
• Vapor Pressure: 7.27E-05mmHg at 25°C
• Refractive Index: 1.495
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Soluble in chloroform.
• BRN: 519324
• CAS DataBase Reference: 2',4',6'-TRIMETHOXYACETOPHENONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2',4',6'-TRIMETHOXYACETOPHENONE(832-58-6)
• EPA Substance Registry System: 2',4',6'-TRIMETHOXYACETOPHENONE(832-58-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 832-58-6(Hazardous Substances Data)

Usage

Description

2',4',6'-Trimethoxyacetophenone is an organic compound that features a core structure of acetophenone with three methoxy groups attached at the 2', 4', and 6' positions. It is characterized by its aromatic properties and functional groups, which make it a versatile intermediate in the synthesis of various organic compounds.

Uses

Used in Pharmaceutical Industry:
2',4',6'-Trimethoxyacetophenone is used as a key intermediate in the synthesis of 4,2',4',6'-tetramethoxy-chalcone, a compound with potential pharmaceutical applications. This chalcone derivative may exhibit biological activities that are beneficial in the development of new drugs or therapeutic agents.
Used in Organic Synthesis:
In the field of organic synthesis, 2',4',6'-trimethoxyacetophenone serves as a valuable building block for the creation of a wide range of organic compounds. Its unique structure allows for various chemical reactions, such as condensation, substitution, and rearrangement, which can lead to the formation of novel molecules with diverse applications in different industries.

Preparation

Preparation by reaction of dimethyl sulfate with phloroacetophenone.

InChI:InChI=1/C11H14O4/c1-7(12)11-9(14-3)5-8(13-2)6-10(11)15-4/h5-6H,1-4H3

Upstream product

• 621-23-8 1,2,3-trimethoxybenzene 
• 108-24-7 acetic anhydride 
• 75-36-5 acetyl chloride 
• 64-19-7 acetic acid 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 7446-70-0 aluminium trichloride 
• 861015-19-2 1,3,5-tris-methoxycarbonyloxy-benzene 
• 570-02-5 2,4,6-trimethoxybenzoic acid 
• 75-05-8 acetonitrile 
• 38447-66-4 acetyl phenyl selenide 
• 108-73-6 3,5-dihydroxyphenol 
• 90-24-4 2-hydroxy-4,6-dimethoxyacetophenone 

Downstream Products

• 61777-22-8 (2E)-1-(2,4,6-trimethoxyphenyl)-3-(4-hydroxyphenyl)-2-propen-1-one 
• 25163-67-1 2',4,4',6'-tetramethoxychalcone 
• 76650-20-9 1-(2,4,6-trimethoxyphenyl)-3-(3,4-dimethoxyphenyl)propenone 
• 480-27-3 1-Methyl-3-(2',4',6'-trimethoxyphenyl)propan-1,3-dione 
• 273211-30-6 1-phenyl-3-(2,4,6-trimethoxy-phenyl)-propane-1,3-dione 
• 273211-51-1 1-(2,4-dimethoxy-phenyl)-3-(2,4,6-trimethoxy-phenyl)-propane-1,3-dione 
• 273211-47-5 1-(4-methoxy-phenyl)-3-(2,4,6-trimethoxy-phenyl)-propane-1,3-dione 
• 856814-55-6 1-(2-benzyloxy-4-methoxy-phenyl)-3-(2,4,6-trimethoxy-phenyl)-propane-1,3-dione 
• 147729-30-4 (2E)-1-(2,4,6-trimethoxyphenyl)-3-(2-methoxyphenyl)-2-propen-1-one 
• 70909-44-3 2,4-dioxo-4-(2,4,6-trimethoxy-phenyl)-butyric acid ethyl ester 
• 25163-69-3 2,2',4,4',6'-pentamethoxychalcone 
• 25163-69-3 2,4,2',4',6'-pentamethoxy-trans-chalcone 

Relevant articles and documents

Phloroglucinol derivatives as anti-tumor agents: synthesis, biological activity evaluation and molecular docking studies

Phloroglucinol compounds isolated from Dryopteris fragrans (L.) Schott showed a variety of biological activities, such as anticancer and anti-inflammatory. In this study, we have made a number of modifications around the scaffold of phloroglucinol and synthesized phloroglucinol derivatives A1–A9, B1–B9, and C1–C3. We synthesized these compounds and investigated their effect on four human cancer cell lines (A-549, MCF-7, Hela, HepG2 cell lines) via MTT assay in vitro. The results revealed that all compounds exhibited certain antiproliferative activities on cancer cell lines and excellent inhibitory effects on MCF-7, in which compound C2 was the best with the IC50 value of 18.49 μM, exceeding that of 5-fluorouracil. Moreover, the cell apoptosis test showed that compound C2 induced apoptosis in a concentration-dependent manner. Furthermore, the results of molecular docking analysis explained the probable interaction between the active compounds and active sites of target protein 4I22 and 1OG5. [Figure not available: see fulltext.]

Dihydropyrazole MurA enzyme inhibitor molecule as well as preparation method and application thereof

The invention provides a dihydropyrazole MurA enzyme inhibitor molecule as well as a preparation method and application thereof. The structural formula is shown in the specification, R is a direct-connected alkyl group with the chemical formula of CnH2n+1, and n is equal to 1-7. The preparation method comprises the following steps of by taking acetophenone substances with different substituent groups and 4-(4-methyl piperazinyl) benzaldehyde as raw materials, carrying out aldol condensation reaction under an alkaline condition to obtain an intermediate, and synthesizing a target compound with a structural formula by using the intermediate, hydrazine hydrate and an organic acid with an R-COOH structure. The dihydropyrazole MurA enzyme inhibitor molecule provided by the invention has a bacterial inhibition effect, has an MurA enzyme inhibition effect, and also has an effect of interfering synthesis of bacterial cell walls.

Synthetic method for portulacanone compounds and their derivatives and anti-inflammatory pharmaceutical compounds containing thereof

The present inventors synthesized described portulacanone derivatives (compound 1: R^1, R^2 = H; and compound 2: R^1, R^2 = H), natural homoisoflavonoids (andplusmn;)-portulacanone A-C (compound 4: R^1 = OMe, R^2 = H; compound 8: R^1, R^2 = OMe; and compound 9: R^1 = OH, R^2 = OMe), and derivatives thereof (compound 3: R^1 = OMe, R^2 = H; compound 5: R^1 = OH, R^2 = H, and compound 7: R^1, R^2 = OMe), and thus evaluated ability to inhibit NO production in LPS-induced RAW 264.7 macrophages as an indicator of anti-inflammatory activity. All tested compounds showed no clear cytotoxicity and inhibited NO production in a concentration dependent manner in RAW 264.7 macrophages. A compound 3 (97.2% inhibition at 10 andmu;M; IC50 = 1.26 andmu;M) shows a significant inhibition effect compared to a compound 1 (91.4% inhibition at 10 andmu;M; IC50 = 1.75 andmu;M) and a compound 7 (83.0% inhibition at 10 andmu;M; IC50 = 2.91 andmu;M). Compounds of the present invention are useful for developing NO producing targeted anti-inflammatory drugs.COPYRIGHT KIPO 2019