1916-08-1

Usage

Uses

Used in Organic Synthesis:
3-Hydroxy-4,5-dimethoxybenzoic acid is used as a key intermediate in organic synthesis for the production of various pharmaceuticals and natural products. Its unique structure allows for versatile chemical reactions, making it a valuable building block in the synthesis of complex organic molecules.
Used in Pharmaceutical Industry:
3-Hydroxy-4,5-dimethoxybenzoic acid is used as a precursor in the development of new drug molecules. Its potential biological activities, such as anti-inflammatory and antioxidant properties, make it a promising candidate for the creation of novel therapeutic agents.
Used in Drug Discovery:
3-Hydroxy-4,5-dimethoxybenzoic acid is utilized in drug discovery research to explore its potential as a lead compound for the development of new pharmaceuticals. Its unique chemical structure and biological activities provide a foundation for further optimization and modification to enhance its therapeutic potential.

InChI:InChI=1/C9H10O5/c1-13-7-4-5(9(11)12)3-6(10)8(7)14-2/h3-4,10H,1-2H3,(H,11,12)

Upstream product

• 29970-32-9 3-benzoyloxy-4,5-dimethoxy-benzoic acid methyl ester 
• 149-91-7 3,4,5-trihydroxybenzoic acid 
• 77-78-1 dimethyl sulfate 
• 29865-90-5 3-hydroxy-4,5-dimethoxybenzaldehyde 
• 2973-76-4 5-bromo-4-hydroxy-3-methoxybenzaldehyde 
• 6948-30-7 5-bromoveratralaldehyde 
• 121-33-5 vanillin 
• 29970-30-7 3,5-diacetoxy-4-benzoyloxy-benzoic acid 
• 29970-31-8 3-benzoyloxy-4,5-dihydroxy-benzoic acid 
• 29970-29-4 3,5-diacetoxy-4-hydroxy-benzoic acid 
• 20731-48-0 3-bromo-4,5-dimethoxybenzoic acid 
• 186581-53-3 diazomethane 
• 91004-48-7 4,5-Dimethoxy-3-nitrobenzoic acid 
• 83011-43-2 3-hydroxy-4,5-dimethoxybenzoate 

Downstream Products

• 83011-43-2 3-hydroxy-4,5-dimethoxybenzoate 
• 86109-27-5 3,4-dimethoxy-5-(3,4,5-trimethoxy-benzoyloxy)-benzoic acid 
• 214849-37-3 3-ethoxy-4,5-dimethoxy-benzoic acid 
• 854872-79-0 3,4-dimethoxy-5-methoxycarbonyloxy-benzoic acid 
• 82448-57-5 5-hydroxy-3,4-dimethoxyphthaldehydic acid 
• 111394-54-8 tert-butyldimethylsilyl 3-tert-butyldimethylsilyloxy-4,5-dimethoxy-benzoate 
• 111394-55-9 3-<(tert-butyldimethylsilyl)oxy>-4,5-dimethoxybenzyl alcohol 
• 111394-57-1 3-tert-butyldimethylsilyloxy-4,5-dimethoxybenzyltriphenylphosphonium bromide 
• 111394-56-0 3-tert-butyldimethylsilyloxy-4,5-dimethoxybenzyl bromide 
• 111394-59-3 3,3'-bis-(tert-butyldimethylsilyloxy)-4',4,5-trimethoxy-(E)-stilbene 
• 1609261-25-7 3-pivaloyloxy-4,5-dimethoxybenzoic acid 

Relevant academic research and scientific papers

MACROCYCLIC DIAMINE DERIVATIVES AS ENT INHIBITORS FOR THE TREATMENT OF CANCERS, AND COMBINATION THEREOF WITH ADENOSINE RECEPTOR ANTAGONISTS

The present invention relates to macrocyclic diamine derivatives of formula II, including pharmaceutically acceptable salts and solvates thereof. Compounds of the invention are inhibitors of ENT family transporter, especially of ENT1, and are useful as therapeutic compounds for the treatment of cancers. The invention also relates to the combined use of the macrocyclic diamine derivatives with an adenosine receptor antagonist, for the treatment of cancers.

Synthesis and in vitro antimalarial activity of alkyl esters of gallate as a growth inhibitor of plasmodium falciparum

This study is aimed to synthesize alkyl esters gallate and determine its in vitro antimalarial activity against parasite Plasmodium falciparum. Fourteen compounds of alkyl esters gallate were synthesized by esterification of the carboxyl group of gallic acid with a series of alkyl alcohols, as well as methoxylation of the hydroxy groups on the aromatic ring of gallic acid. Antimalarial activity of the synthesized alkyl esters gallate were expressed by IC50 value, with gallic acid as an original compound and artemisin as a positive control. Compared to gallic acid, eleven synthesized compounds of alkyl esters gallate, have a greater antimalarial activity against Plasmodium falciparum. On the other hand, three compounds, that are propyl gallate, butyl gallate and trimethoxy methyl gallate, showed a lower antimalarial activity. Moreover, compared to gallic acid (IC50: 194.86 mM) and artemisin (IC50: 0.5 mM), two synthesized compounds of alkyl gallates, namely methyl gallate and hexyl gallate exhibited the stronger antimalarial activity against Plasmodium falciparum, with IC50 value of 0.03 mM and 0.11 mM, respectively. Our result clearly demonstrated that methyl gallate and hexyl gallate as a promising candidate for the new antimalarial agents.

Synthesis and cytotoxic activities of hexyl-esters derivatives of gallic acid against MCF-7 cell line

Gallic acid is found in many plants, fruits, and foods where the anti-cancer activity is found. However, gallic acid has a problem on the high polarity and low bio availability. So, it takes molecular modifications in order to increase its lipophilicity, which is expected to increase bio availability and cytotoxic activity of gallic acid. Hexyl esters derivatives of gallic acid were synthesized and characterized by spectrometer 1H-NMR, 13C-NMR, mass spectrometry and infrared spectrophotometer (FTIR). All compounds were then evaluated for cytotoxic activity on MCF-7 cell line using MTT method. Compound cis-2′-hexenyl-3,4,5-trimethoxygallate (19) had the lowest IC50 value compared with gallic acid and other derivatives hexyl esters. IC50 value of cis-2′-hexenyl-3,4,5-trimethoxygallate (19) is 14.48 μg/ml. Compound (19) also has approached with IC50 values of gossypol as a positive control. Compound (19) is a potential compound to inhibit growth of MCF-7 cell line.

Synthesis and biological evaluation of phenstatin metabolites

Previous investigations on the incubation of phenstatin with rat and human microsomal fractions revealed the formation of nine main metabolites. The structures of eight of these metabolites have been now confirmed by synthesis and their biological properties have been reported. Eaton's reagent was utilized as a convenient condensing agent, allowing, among others, a simple multigram scale preparation of phenstatin. Synthesized metabolites and related compounds were evaluated for their antiproliferative activity in the NCI-60 cancer cell line panel, and for their effect on microtubule assembly. Metabolite 23 (2′-methoxyphenstatin) exhibited the most potent in vitro cytotoxic activity: inhibition of the growth of K-562, NCI-H322M, NCI-H522, KM12, M14, MDA-MB-435, NCI/ADR-RES, and HS 578T cell lines with GI50 values 50 = 3.2 μM vs 15.0 μM) and induced G2/M arrest in murine leukemia DA1-3b cells. The identification of this active metabolite led to the design and synthesis of analogs with potent in vitro cytotoxicity and inhibition of microtubule assembly.

Cloning and heterologous expression of two aryl-aldehyde dehydrogenases from the white-rot basidiomycete Phanerochaete chrysosporium

We identified two aryl-aldehyde dehydrogenase proteins (PcALDH1 and PcALDH2) from the white-rot basidiomycete Phanerochaete chrysosporium. Both PcALDHs were translationally up-regulated in response to exogenous addition of vanillin, one of the key aromatic compounds in the pathway of lignin degradation by basidiomycetes. To clarify the catalytic functions of PcALDHs, we isolated full-length cDNAs encoding these proteins and heterologously expressed the recombinant enzymes using a pET/Escherichia coli system. The open reading frames of both PcALDH1 and PcALDH2 consisted of 1503 nucleotides. The deduced amino acid sequences of both proteins showed high homologies with aryl-aldehyde dehydrogenases from other organisms and contained ten conserved domains of ALDHs. Moreover, a novel glycine-rich motif "GxGxxxG" was located at the NAD+-binding site. The recombinant PcALDHs catalyzed dehydrogenation reactions of several aryl-aldehyde compounds, including vanillin, to their corresponding aromatic acids. These results strongly suggested that PcALDHs metabolize aryl-aldehyde compounds generated during fungal degradation of lignin and various aromatic xenobiotics.

Synthesis of 1,2,6-Trihydroxy-7,8-dimethoxy-3-methylanthraquinone

A new anthraquinone, 1,2,6-trihydroxy-7,8-dimethoxy-3-methylanthraquinone (I) has been synthesised by condensing 5-hydroxy-3,4-dimethoxyphthalic anhydride (III) with 3-methylcatechol (IV) in the presence of anhyd. aluminium chloride, followed by cyclisation of the resultant o-benzoylbenzoic acid derivative, 2',3',5-trihydroxy-3,4-dimethoxy-4'-methyl-2-benzoylbenzoic acid (II), with sulphuric acid containing boric acid.