1131-94-8

Usage

Uses

Used in Pharmaceutical Industry:
3-Hydroxy-4-methoxyphenylacetic acid is used as an intermediate compound for the synthesis of various pharmaceutical products. Its role as a metabolite of DOPA analogues and Hydroxytyrosol makes it a valuable component in the development of medications targeting neurological and neurodegenerative disorders.
Used in Research and Development:
3-Hydroxy-4-methoxyphenylacetic acid is utilized as a research compound in the field of biochemistry and pharmacology. It aids in understanding the metabolic pathways of catecholamines and their derivatives, which can contribute to the development of new therapeutic strategies for related health conditions.
Used in Analytical Chemistry:
As a metabolite of various compounds, 3-Hydroxy-4-methoxyphenylacetic acid can be used as a reference material or standard in analytical chemistry for the identification and quantification of similar compounds in biological samples, helping to improve the accuracy and reliability of analytical methods.

Synthesis Reference(s)

The Journal of Organic Chemistry, 49, p. 2061, 1984 DOI: 10.1021/jo00185a061

InChI:InChI=1/C9H10O4/c1-13-8-3-2-6(4-7(8)10)5-9(11)12/h2-4,10H,5H2,1H3,(H,11,12)

Upstream product

• 73357-19-4 (5-hydroxy-4-methoxy-2-nitro-phenyl)-acetic acid 
• 199992-39-7 (3-hydroxy-4-methoxy-phenyl)-glyoxylic acid 
• 63304-81-4 2-(3-amino-4-methoxyphenyl)acetic acid 
• 162470-38-4 (3-acetoxy-4-methoxy-phenyl)-acetonitrile 
• 5487-33-2 O-benzylhomoisovanillic acid 
• 774-81-2 (3-bromo-4-methoxy-phenyl)-acetic acid 
• 4468-58-0 3-hydroxy-4-methoxyphenylacetonitrile 
• 89936-29-8 2-(3,5-dibromo-4-methoxyphenyl)acetic acid 
• 81038-48-4 2-bromo-4-methoxy-5-hydroxylphenylacetic acid 
• 81038-49-5 2-Chloro-5-hydroxy-4-methoxyphenylacetic acid 
• 129249-75-8 4-methoxy-3-(o-nitrobenzyloxy)phenylacetic acid 
• 70028-57-8 (3-hydroxy-4-methoxy-phenyl)-pyruvic acid 
• 7722-84-1 dihydrogen peroxide 
• 81038-46-2 2-Chloro-5-hydroxy-4-methoxyphenylacetonitrile 

Downstream Products

• 861323-48-0 (3-ethoxycarbonyloxy-4-methoxy-phenyl)-acetic acid 
• 18929-89-0 1-(3-Hydroxy-4-methoxybenzylcarbonyl)-3,4-dimethoxybenzol 
• 21411-19-8 N-(β-4-hydroxy-3-methoxyphenethyl)-(3-hydroxy-4-methoxyphenyl)acetamide 
• 15964-81-5 methyl 3-hydroxy-4-methoxyphenylacetate 
• 80367-35-7 (3-Hydroxy-4-methoxy-2,6-bis-morpholin-4-ylmethyl-phenyl)-acetic acid 
• 81038-48-4 2-bromo-4-methoxy-5-hydroxylphenylacetic acid 
• 203441-77-4 3-(3-Cyclopentyloxy-4-methoxy-phenyl)-2-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 203441-28-5 3-(3-Cyclopentyloxy-4-methoxy-phenyl)-3-pyridin-4-ylmethyl-pyrrolidin-2-one 
• 203440-78-2 3-(3-cyclopentyloxy-4-methoxy-phenyl)-2-oxo-3-pyridin-4-ylmethyl-pyrrolidine-1-carboxylic acid tert-butyl ester 

Relevant academic research and scientific papers

One-Pot Biocatalytic In Vivo Methylation-Hydroamination of Bioderived Lignin Monomers to Generate a Key Precursor to L-DOPA

Electron-rich phenolic substrates can be derived from the depolymerisation of lignin feedstocks. Direct biotransformations of the hydroxycinnamic acid monomers obtained can be exploited to produce high-value chemicals, such as α-amino acids, however the reaction is often hampered by the chemical autooxidation in alkaline or harsh reaction media. Regioselective O-methyltransferases (OMTs) are ubiquitous enzymes in natural secondary metabolic pathways utilising an expensive co-substrate S-adenosyl-l-methionine (SAM) as the methylating reagent altering the physicochemical properties of the hydroxycinnamic acids. In this study, we engineered an OMT to accept a variety of electron-rich phenolic substrates, modified a commercial E. coli strain BL21 (DE3) to regenerate SAM in vivo, and combined it with an engineered ammonia lyase to partake in a one-pot, two whole cell enzyme cascade to produce the l-DOPA precursor l-veratrylglycine from lignin-derived ferulic acid.

Simple inorganic base promoted C-N and C-C formation: synthesis of benzo[4,5]imidazo[1,2-a]pyridines as functional AIEgens used for detecting picric acid

Metal-free catalyzed intermolecular tandem Michael addition/cyclization has been developed for the synthesis of benzo[4,5]imidazo[1,2-a]pyridines from α-bromocinnamaldehyde and 2-substituted benzimidazoles. The reaction promoted by a simple inorganic base displays moderate to good yields and good functional group tolerance. The optical properties of some typical products have been investigated. We found that, due to the presence of the benzene ring at the C1-position of benzo[4,5]imidazo[1,2-a]pyridines which restricts intramolecular motion, as a new type of aggregation-induced emission (AIE) luminogen (AIEgen), they show very good solid-state fluorescence with quantum yields up to 88.80%. Importantly, the AIE performance of compound3bcan be useful to detect the nitroaromatic explosive picric acid (PA) with a detection limit and quenching constant of 42.5 nM and 7.27 × 104M?M, respectively.

COMPOUND AND AN ORGANIC SEMICONDUCTING LAYER, AN ORGANIC ELECTRONIC DEVICE AND A DISPLAY OR LIGHTING DEVICE COMPRISING THE SAME

The present invention relates to a compound having the formula (I); and an organic semiconducting layer, an organic electronic device, a display device and a lighting device comprising the same.

Asymmetric total synthesis of tetrahydroprotoberberine derivatives and evaluation of their binding affinities at dopamine receptors

Cocaine addiction remains a serious challenge for clinical and medical research because there is no effective pharmacological treatment. L-THP, a natural product isolated from Corydalis yanhusuo W.T. Wang, is one of the most frequently used traditional herbs to treat drug addiction in China. Our laboratory first reported that its demethylated metabolites L-ICP, L-CD, and L-CP had high affinity at dopamine D1, D2, and D5 receptors. Here we report the chemical synthesis of these metabolites and other derivatives and their binding affinities at dopamine receptors. The synthesis of these bioactive metabolites will allow further in vivo study of their potential in treating cocaine addiction.

Tetrahydropalmatine derivative and application thereof

The invention relates to a tetrahydropalmatine derivative and application thereof, a compound as shown in a formula (VI) and a preparation method thereof, and an application of the compound in medicine. Specifically, the invention relates to a derivative of the compound as shown in the general formula (VI) and a preparation method thereof, and an application of the derivative as a therapeutic agent in prevention and treatment of hyperlipidemia, hypercholesterolemia, hypertriglyceridemia, hepatic steatosis, diabetes type II, hyperglycemia, adiposis, or insulin resistance and metabolic syndrome. The compound disclosed by the invention also can reduce total cholesterol, low density lipoprotein (LDL)-cholesterol and triglycerides, and increases the expression of a liver LDL receptor and inhibits the expression of proprotein convertase subtilisin/kexin type 9 (PCSK9).

Tetrahydroberberine derivative and application thereof

The invention relates to a tetrahydroberberine derivative and application thereof and relates to a compound represented by a formula (V) shown in the description, a preparation method therefor and application of the compound in medicine. Particularly, the invention relates to a derivative of the compound represented by the general formula (V), a preparation method for the derivative of the compound and use of the derivative of the compound in the prevention and treatment of hyperlipidemia, hypercholesterolemia, hypertriglyceridemia, fatty degeneration of liver, type II diabetes, hyperglycemia, obesity or insulin resistance syndrome and metabolic syndrome. The compound disclosed by the invention can also be used for lowering total cholesterol, LDL (Low-Density Lipoprotein)-cholesterol and triglyceride, improving liver LDL receptor expression and inhibiting PCSK9 expression.

Tetrahydrocoptisine derivative and applications thereof

The present invention relates to a compound as shown in a formula (VII), a preparation method and applications thereof in medicines. In particular, the present invention relates to a derivative of the compound as shown in the formula (VII), a preparation method, and the applications of the derivative used as a therapeutic agent in prevention and treatment of hyperlipidemia, hypercholesterolemia, hypertriglyceridemia, hepatic steatosis, II-type diabetes, hyperglycemia, obesity or insulin resistance syndrome and metabolic syndrome. The compound disclosed by the present invention can also reduce total cholesterol, LDL-cholesterol and triglyceride, and increases expression of a liver LDL receptor and decreases expression of PCSK9.

Synthesis and Study of α-Glucosidase Inhibitory, Antimicrobial and Antioxidant Activities of Some Benzimidazole Derivatives Containing Triazole, Thiadiazole, Oxadiazole, and Morpholine Rings

A new series of 2-(4-bromobenzyl)- and 2-(4-fluorobenzyl)-1H-benzimidazole derivatives containing 1,2,4-triazole, 1,3,4-thiadiazole, 1,3,4-oxadiazole, and morpholine rings has been synthesized. The structures of the newly synthesized compounds were confirmed by 1H and 13C NMR and mass spectra, and all substances have been screened for their α-glucosidase inhibitory, antimicrobial and antioxidant activities. Hydrazide, oxadiazole, thiosemicarbazide, and 1,2,4-triazole-3-thiol derivatives showed very good ABTS scavenging activities (IC50 1.94-4.79 μM). Oxadiazole and thiosemicarbazide derivatives also revealed notable DPPH scavenging activity. 5-[(2-(4-Bromobenzyl)-1H-benzimidazol-1-yl)methyl]-1,3,4-oxadiazole-2-thiol was found to be more potent than acarbose. 2-(4-Fluorobenzyl)-1H-benz- imidazole was effective against both Gram-positive and Gram-negative bacteria, especially, M. smegmatis.

Asymmetric total synthesis and identification of tetrahydroprotoberberine derivatives as new antipsychotic agents possessing a dopamine D1, D2 and serotonin 5-HT1A multi-action profile

An effective and rapid method for the microwave-assisted preparation of the key intermediate for the total synthesis of tetrahydroprotoberberines (THPBs) including l-stepholidine (l-SPD) was developed. Thirty-one THPB derivatives with diverse substituents on A and D ring were synthesized, and their binding affinity to dopamine D1, D2 and serotonin 5-HT 1A and 5-HT2A receptors were determined. Compounds 18k and 18m were identified as partial agonists at the D1 receptor with Ki values of 50 and 6.3 nM, while both compounds act as D2 receptor antagonists (Ki = 305 and 145 nM, respectively) and 5-HT1A receptor full agonists (Ki = 149 and 908 nM, respectively). These two THPBs compounds exerted antipsychotic actions in animal models. Further electrophysiological studies employing single-unit recording in intact animals demonstrated that 18k-excited dopaminergic (DA) neurons are associated with its 5-HT1A receptor agonistic activity. These results suggest that these two compounds targeted to multiple neurotransmitter receptors may present novel lead drugs with new pharmacological profiles for the treatment of schizophrenia.

Weinreb amide as an efficient reagent in the one pot synthesis of benzimidazoles and benzothiazoles

One pot synthesis of 2-substituted benzimidazoles/benzothiazoles through condensation is followed by cyclization of Weinreb amide with o-diaminoarene or o-aminothiophenol is reported. In the presence of boron trifluoride etherate in 1,4-dioxane solvent, a high yield (75-94%) was achieved within 60 min. Weinreb amide shows high selectivity in the reaction, even in presence of other active functional groups such as carboxyl, halogen, cyano, and methoxy.