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

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

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

Downstream Products

• 25163-67-1 2',4,4',6'-tetramethoxychalcone 
• 76650-20-9 1-(2,4,6-trimethoxyphenyl)-3-(3,4-dimethoxyphenyl)propenone 
• 76650-20-9 (2E)-1-(2,4,6-trimethoxyphenyl)-3-(3,4-dimethoxyphenyl)-2-propen-1-one 
• 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 
• 90-24-4 2-hydroxy-4,6-dimethoxyacetophenone 
• 530-55-2 2,6-dimethoxy-p-quinone 
• 3602-54-8 4,6-dihydroxy-2-methoxyacetophenone 

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

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

Inventors of the present invention synthesized natural homoisoflavonoid portulacanone D (compound 6) isolated from Portulaca oleracea L (POL). An ability to inhibit NO production in LPS-induced RAW 264.7 macrophages was assessed as an indicator of anti-inflammatory activity. The tested portulacanone D did not show clear cytotoxicity and inhibited NO production in the RAW 264.7 macrophages in a concentration dependent manner. The portulacanone D exhibits 92.5% of NO production inhibition at 10 andmu;M and has an IC50 value of 2.09 andmu;M. The finding has additional correlation with the suppressed expression of iNOS induced by LPS. According to the information obtained from the study of the present invention, the portulacanone D can be used in the development of anti-inflammatory drugs targeting NO production.COPYRIGHT KIPO 2019

The winding road of the uvaretin class of natural products: From total synthesis to bioactive agent discovery

Herein, we disclose the development of a synthetic route to gain access to the uvaretin class of chalcone natural products. In this, the construction of a small library was achieved, and the collection was evaluated for cytotoxicity and other biological properties. Uvaretin (1) was accessed via a seven-step route in an overall yield of 15.1%. Within this route, the unsaturated enone variant of uvaretin (2), also a natural product, was accessed in a 16.7% yield over six steps. This route provides a nearly three-fold increase in yields of 1 and 2 in comparison to the previous synthetic route accessing them in 5.8% and 3.0% overall yields, respectively. Evaluation of 1 and 2 revealed IC50 values between 2.0 and 5.1 μM in the cancerous cell lines HeLa, U937, A549, and MIA PaCa-2. Screening of the whole chalcone library set led to the discovery of over 30 compounds, within six cancerous cell lines, possessing single digit μM IC50 activity as sole agents. Furthermore, multiple library members were found to possess promising potentiating properties with known chemotherapeutic agents.

Hydrogen bond donor solvents enabled metal and halogen-free Friedel–Crafts acylations with virtually no waste stream

We have developed a metal and halogen-free Friedel–Crafts acylation protocol with virtually no waste stream generation. We propose a hydrogen bonding donor solvent will form a hydrogen bonding network and may provide significant rate enhancement for Friedel–Crafts reactions. Trifluoroacetic acid is one of the strongest H-bond donor solvents, which is also volatile and can be easily recovered by distillation without need for reaction workup. Our protocol is a ‘green’ Friedel–Crafts acylation process: 1) the catalyst can be recovered and reused; 2) using halogen free starting material (carboxylic acids anhydride or carboxylic acids); 3) no need for aqueous reaction work-up; 4) minimum or no waste steam generation.

Synthesis and in vitro evaluation of homoisoflavonoids as potent inhibitors of nitric oxide production in RAW-264.7 cells

Syntheses of natural homoisoflavonoids, (±)-portulacanones A–C (4, 8 and 9), portulacanone D (6), isolated from Portulaca oleracea L. (POL) and their derivatives (3, 5 and 7) have been achieved for the first time along with the synthesis of known derivatives (1 and 2) and their in vitro inhibitory effect against NO production in LPS-induced RAW-264.7 macrophages was evaluated as an indicator of anti-inflammatory activity. All the compounds tested had a concentration-dependent inhibitory effect on NO production by RAW-264.7 macrophages without obvious cytotoxicity. Compounds 3 (97.2% at 10 μM; IC50 = 1.26 μM) followed by 6 (portulacanone D) (92.5% at 10 μM; IC50 = 2.09 μM), 1 (91.4% at 10 μM; IC50 = 1.75 μM) and 7 (83.0% at 10 μM; IC50 = 2.91 μM) were the most potent from the series. This finding was further correlated with the suppressed expression of iNOS induced by LPS. Our promising preliminary results may provide the basis for the assessment of compound 3 as a lead structure for a NO production-targeted anti-inflammatory drug development and also could support the usefulness of POL as a folklore medicinal plant in the treatment of inflammatory diseases.

Novel neohesperidin dihydrochalcone analogue inhibits adipogenic differentiation of human adipose-derived stem cells through the Nrf2 pathway

Obesity, characterized by excess lipid accumulation, has emerged as a leading public health problem. Excessive, adipocyte-induced lipid accumulation raises the risk of metabolic disorders. Adipose-derived stem cells (ASCs) are mesenchymal stem cells (MSCs

P -Selective (sp2)-C-H functionalization for an acylation/alkylation reaction using organic photoredox catalysis

p-Selective (sp2)-C-H functionalization of electron rich arenes has been achieved for acylation and alkylation reactions, respectively, with acyl/alkylselenides by organic photoredox catalysis involving an interesting mechanistic pathway.