6512-33-0

Usage

Uses

Used in Pharmaceutical Industry:
Benzeneacetic acid, 2-acetyl-3,5-dimethoxy-, methyl ester is used as an intermediate in the synthesis of various psychoactive substances and pharmaceutical compounds. Its unique chemical structure allows it to be a key component in the production of certain medications.
Used in Illicit Drug Production:
Unfortunately, Benzeneacetic acid, 2-acetyl-3,5-dimethoxy-, methyl ester is also commonly used in the production of illicit drugs such as MDMA (ecstasy) and other psychoactive stimulants. Its psychoactive properties make it a target for misuse and abuse, leading to its involvement in the illegal drug trade.

Upstream product

• 6512-32-9 methyl 2-(3,5-dimethoxyphenyl)acetate 
• 108-24-7 acetic anhydride 
• 1203549-54-5 3,5-dimethoxy-2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 105-45-3 acetoacetic acid methyl ester 
• 75-36-5 acetyl chloride 

Downstream Products

• 17276-03-8 1,3,6,8-tetramethoxynaphthalene 
• 13586-04-4 3,6,8-trimethoxy-1-naphthol 
• 1422166-77-5 methyl 2-(2-acetyl-3-hydroxy-5-methoxyphenyl)acetate 
• 126495-72-5 methyl 2-(2-acetyl-3,5-dihydroxyphenyl)acetate 
• 36440-12-7 2-hydroxy-5,7-dimethoxy-1,4-naphthoquinone 
• 959586-96-0 C₁₄H₁₈O₆ 
• 64954-45-6 6,8-dihydroxy-1,3-dimethoxynaphthalene 

Relevant academic research and scientific papers

Target ROS to induce apoptosis and cell cycle arrest by 5,7-dimethoxy-1,4-naphthoquinone derivative

The 1,4-naphthoquinone derivatives bearing 5,7-dimethoxyl moiety were designed, synthesized, and tested as the antitumor agents against five human cancer cell lines (A549, Hela, HepG2, NCI-H460 and HL-60). All the compounds are described herein for the first time. The structure-activity relationships indicated that the presence of chlorine atom at the 2-position was crucial for the antiproliferative activity. Further, the electrochemical properties of the representative compounds (7e, 8e and 9e) were evaluated and a definite correlation between the redox potential and the antiproliferative activity. The most potent compound 9e displayed significant anti-leukemic activity with IC50 value of 3.8 μM in HL-60 cells and weak cytotoxicity with IC50 of 40.7 μM in normal cells WI-38. In mechanistic study for 9e, the increased numbers of apoptotic cells and increased cell population at G2/M phase correlated with ROS generation. Together, our results suggested that the derivatives of 2-chlorine-1,4-naphthoquinone might be the promising candidates for the treatment of promyelocytic leukemia.

A unifying paradigm for naphthoquinone-based meroterpenoid (bio)synthesis

Bacterial meroterpenoids constitute an important class of natural products with diverse biological properties and therapeutic potential. The biosynthetic logic for their production is unknown and defies explanation via classical biochemical paradigms. A l

Biosynthetically Guided Structure–Activity Relationship Studies of Merochlorin A, an Antibiotic Marine Natural Product

The onset of new multidrug-resistant strains of bacteria demands continuous development of antibacterial agents with new chemical scaffolds and mechanisms of action. We present the first structure–activity relationship (SAR) study of 16 derivatives of a s

Biomimetic synthesis of (±)-merochlorin B

A short total synthesis, guided by biosynthetic considerations, of racemic merochlorin B is presented. The formation of its isomer, merochlorin A, was not observed under the conditions. Key steps include a directed ortho-metalation (DoM), a selective demethylation, an ortho-allylation, and an oxidative [3 + 2]-cycloaddition mediated by an iodine(III) reagent.

First syntheses of the biologically active fungal metabolites pestalotiopsones A, B, C and F

A synthetic approach accessing the pestalotiopsones, fungal chromones possessing a rare skeletal subtype, is reported for the first time. The synthesis of pestalotiopsone A (1) has been achieved in 7 linear steps (28%), from commercially available 3,5-dim

Stereochemical assignment of the fungal metabolites pestalotiopsones D and e through enantiopure synthesis

The pestalotiopsones are fungal metabolites isolated from an endophytic fungus Pestalotiopsis sp. found in the mangrove Rhizophora mucronata, used in traditional Chinese medicine to treat symptoms of dysentery. The absolute configurations of pestalotiopso

Biomimetic total synthesis of (±)-merochlorina

Inspired: The proposed biosynthetic pathway toward the potent antibiotic meroterpenoid (±)-merochlorinA inspired its concise total synthesis. The key steps in the synthesis are a one-pot aromatization-alkylation reaction, followed by a biomimetic oxidativ

Expedient synthesis of 3-hydroxyisoquinolines and 2-hydroxy-1,4- naphthoquinones via one-pot aryne acyl-alkylation/condensation

A convenient method is disclosed for the synthesis of both 3-hydroxyisoquinolines and 2-hydroxy-1,4-naphthoquinones from β-ketoesters using a one-pot aryne acyl-alkylation/condensation procedure. When performed in conjunction with a one-step method for the synthesis of the β-ketoester substrates, this method provides a new route to these polyaromatic structures in only two steps from commercially available carboxylic acid starting materials. The utility of this approach is demonstrated in the synthesis of the atropisomeric P,N-ligand, QUINAP. The Royal Society of Chemistry 2009.

A metalation strategy for the construction of functionalized naphthalenes: The first synthesis of guieranone A

The first synthesis of the natural product guieranone A is described, demonstrating a one-pot procedure for the synthesis of protected-1,3,6,8- tetraoxygenated naphthalenes and a subsequent directed metalation synthesis of 2-keto naphthalenes.