81574-58-5

Usage

Uses

Used in Flavor and Fragrance Industry:
2,4,6-Trimethoxy-3-methylbenzaldehyde is used as a flavoring agent for its sweet, vanilla-like aroma, enhancing the scent and flavor of food and beverage products. It is particularly popular in the production of ice cream, baked goods, and soft drinks.
Used in Perfumery and Cosmetics:
In the perfumery and cosmetics industry, 2,4,6-trimethoxy-3-methylbenzaldehyde is used as a fixative and scent enhancer. Its pleasant aroma makes it a valuable ingredient in the formulation of perfumes, soaps, and other personal care products.
Used in Pharmaceutical Synthesis:
2,4,6-Trimethoxy-3-methylbenzaldehyde serves as a precursor for the synthesis of various pharmaceuticals and organic compounds. Its chemical properties allow it to be easily modified and incorporated into a wide range of drug molecules, contributing to the development of new medications.
Used in Anti-Inflammatory Applications:
Studies have shown that 2,4,6-trimethoxy-3-methylbenzaldehyde possesses potential anti-inflammatory properties. It is being investigated for its ability to reduce inflammation and alleviate symptoms associated with various inflammatory conditions.
Used in Antioxidant Applications:
As an antioxidant, 2,4,6-trimethoxy-3-methylbenzaldehyde helps protect cells from damage caused by free radicals and oxidative stress. Its presence in food products and cosmetics can contribute to the maintenance of overall health and the prevention of premature aging.
Used in Anti-Cancer Research:
2,4,6-Trimethoxy-3-methylbenzaldehyde is also being studied for its potential anti-cancer properties. Preliminary research suggests that it may have the ability to inhibit the growth of cancer cells and modulate signaling pathways involved in tumor progression, making it a promising candidate for further investigation and development as a cancer therapeutic.

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

Upstream product

• 621-23-8 1,2,3-trimethoxybenzene 
• 14107-97-2 2,4,6-trimethoxytoluene 
• 68-12-2 N,N-dimethyl-formamide 
• 55743-13-0 2,4,6-trihydroxy-3-methylbenzaldehyde 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 171670-29-4 2,4,6-trimethoxy-3-methylbenzenemethanol 
• 643-56-1 2-phenyl-5-methoxy-6-methyl-chromen-7-one 
• 125536-25-6 7-hydroxy-5-methoxy-6-methyl-2-phenyl-1-benzopyrylium perchlorate 
• 55743-13-0 2,4,6-trihydroxy-3-methylbenzaldehyde 
• 118093-05-3 2-methoxy-3-methyl-4,6-dihydroxybenzaldehyde 
• 1447-85-4 2-phenyl-5-methoxy-6-methyl-7-hydroxybenzopyran hydrochloride 
• 81574-59-6 2,4,6-trimethoxy-3-methylphenol 
• 21722-31-6 1-(2-hydroxy-4,6-dimethoxy-3,5-dimethylphenyl)ethanone 
• 1521-61-5 1,3,5-trimethoxy-2,4-dimethyl benzene 

Relevant academic research and scientific papers

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.]

Synthesis of new C-dimethylated chalcones as potent antitubercular agents

A new class of C-dimethylated-chalcones (9a–q) were synthesized by using 2-hydroxy-3,5-dimethyl-4,6-dimethoxy acetophenone as a key intermediate. The compounds were screened for anti-tubercular activity against Mycobacterium tuberculosis strain (H37Rv) by Microplate Alamar Blue assay (MABA) method at a concentration of 100–0.8 μg/mL. The chalcones, 9a, 9b, 9c, 9k, 9o, and 9p were found to have higher antitubercular activity than the standard drugs, while the remaining compounds showed moderate activity. The antitubercular activity of the chalcones, 9b (MIC90 = 3.98 μM) and 9o (MIC90 = 3.84 μM) was found to be more than two-fold more active than the standard drugs, streptomycin (MIC90 = 10.75 μM) and ciprofloxacin (MIC90 = 9.43 μM), while their antitubercular activity was found to be more than six-fold more active than pyrazinamide (MIC90 = 25.38 μM). Further, the molecular docking studies employing Mycobacterium tuberculosis protein tyrosine phosphatase (MtbPtp) was carried out to observe docking scores.

Efficient synthesis of rottlerin and its two subunits

Rottlerin, a natural product isolated from Mallotus philippensis, is associated with a range of biological activities. Its chemical structure is featured by two different substituted phloroglucinol units linked by a methylene group. In this study, we accomplished a total synthesis of rottlerin using phenol-aldehyde condensation as the key reaction. By our method, gram-scale preparation of the two structural subunits was achieved, and rottlerin was obtained in a longest eight linear step with 20% overall yield. Our study provides a practical solution for obtaining the sample of rottlerin in an efficient way.

Preparation methods of dracorhodin and salt and intermediates thereof and intermediate compounds

The invention relates preparation methods of dracorhodin and salt and intermediates thereof and intermediate compounds. Synthesis of multifunctional group-substituted benzene ring core structures, that is, the intermediate compounds V, VI and VII is achieved by taking phloroglucinol trimethyl ether as a starting raw material, combining a formylation reaction, a Huang-Minlon reduction method, a methyl ether demethylation reaction, the reaction that benzyl is introduced onto phenolic hydroxyl through benzyl halogen, the reaction that methyl is introduced onto phenolic hydroxyl by taking dimethyl carbonate as a methylation reagent, a debenzylation reaction, a demethylation reaction and the like, utilizing the intramolecular hydrogen bond effect of formyl and phenolic hydroxyl on benzene rings and controlling the proper reaction conditions through proper combinations of the reactions and a protection-deprotection strategy. According to the method, dracorhodin and the salt thereof are synthesized by adopting the raw material which is low in cost, easy to obtain and low in toxicity, the process route is short, the cost is low, the chemical selectivity of all the steps is high, the total yield reaches up to about 10%, the process reproducibility is good, industrialization can be achieved, and the green and economical properties are achieved.

Total synthesis of wasabidienones B1 and B0 via SIBX-mediated hydroxylative phenol dearomatization

(Chemical Equation Presented) The first total synthesis of the natural nondimerizing o-quinol (+)-wasabidienone B1 was achieved from commercially available 1,3,5-trimethoxybenzene. The key dearomatizing transformation was efficiently accomplished via a hydroxylative phenol dearomatization reaction using the stabilized λ5-iodane reagent IBX (SIBX). (+)-Wasabidienone B1 was then converted into its congener (-)-wasabidienone B0 via an improved thermally induced ring-contracting isomerization reaction.

Synthesis of (+)-(R)-5-hydroxy-6-hydroxymethyl-7-methoxy-8-methylflavanone

The synthesis of (+)-(R)-5-hydroxy-6-hydroxymethyl-7-methoxy-8-methylflavanone is described. A new chromylation method of β-ketosulfoxide 9 leading to the Michael acceptor 12 has been developed. Dilithium tetra-chlorocuprate was shown to be a very efficie

Depsidone Synthesis. Part 21. A New Synthesis of Grisa-2',5'-diene-3,4'-diones

Treatment of suitably substituted methyl 2-phenoxybenzoates with titanium(IV) chloride and dry hydrogen chloride afforded grisa-2',5'-diene-3,4'-diones in high yield.The structures of these compounds followed from their thermal stability, their methanolysis to methyl 2-(4-hydroxyphenoxy)benzoates, and their reductive cleavage to 2,4'-dihydrobenzophenones.Treatment of the benzophenones with base gave xanthones.An attempt to synthesize dehydrogriseofulvin (1) by this method failed.