15964-80-4

Usage

InChI:InChI=1/C10H12O4/c1-13-9-5-7(3-4-8(9)11)6-10(12)14-2/h3-5,11H,6H2,1-2H3

Upstream product

• 97-53-0 4-allylguaiacol 
• 67-56-1 methanol 
• 306-08-1 Homovanillic acid 
• 149-73-5 trimethyl orthoformate 
• 5447-38-1 2-(4-acetoxy-3-methoxyphenyl)acetic acid 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 55-10-7 4-hydroxy-3-methoxy-mandelic acid 
• 90-05-1 2-methoxy-phenol 
• 16209-54-4 methyl 4-benzyloxy-3-methoxyphenylethanoate 

Downstream Products

• 64360-40-3 [4-(4-Allyloxy-3-chloro-benzyloxy)-3-methoxy-phenyl]-acetic acid 
• 29973-91-9 4-benzyloxy-3-methoxyphenylacetic acid 
• 64385-14-4 [4-(4-Isopropyl-benzyloxy)-3-methoxy-phenyl]-acetic acid 
• 15964-84-8 3-methoxy-4-trimethylsilyloxyphenylacetic acid methyl ester 
• 950833-00-8 methyl [4-(3-bromopropoxy)-3-methoxyphenyl]acetate 
• 340255-35-8 Methyl {3-methoxy-4-[2-(tetrahydro-2H-pyran-2-yloxy)ethoxy]phenyl}acetate 
• 950833-01-9 methyl [4-(4-bromobutoxy)-3-methoxyphenyl]acetate 
• 860782-01-0 methyl 4-(2-propiamidoethoxy)-3-methoxyphenylacetate 
• 873011-68-8 3-Methoxy-4-[[(trifluoromethyl)sulfonyl]oxy]benzeneacetic acid methyl ester 
• 15964-79-1 methyl (3,4-dimethoxyphenyl)acetate 
• 1357346-75-8 C₁₇H₁₅NO₈ 
• 29121-49-1 2-(4-hydroxy-3-methoxyphenyl)acetamide 
• 1313364-76-9 [4-((R)-sec-Butoxy)-3-methoxy-phenyl]-acetic acid 
• 1313364-77-0 [4-((R)-sec-Butoxy)-3-methoxy-phenyl]-acetyl chloride 

Relevant academic research and scientific papers

METHOD FOR PRODUCING ESTERS OF HOMOVANILLIC ACID

The present invention primarily relates to a method for producing a compound of formula (I) and/or a physiologically acceptable salt thereof from vanillylmandelic acid and/or a physiologically acceptable salt thereof. The present invention further relates to the simultaneous use of one or more iodide salt(s) or hydrate(s) thereof, one or more reducing agent(s), one or more inorganic and/or organic acid(s) other than phosphonic acid, and methanol and/or a physiologically acceptable salt thereof or an alcohol of formula (II) as defined herein and/or a physiologically acceptable salt thereof for converting vanillylmandelic acid and/or a physiologically acceptable salt thereof into a compound of formula (I) and/or a physiologically acceptable salt thereof or into a compound of formula (III) as defined herein and/or a physiologically acceptable salt thereof.

Biological evaluation of natural and synthesized homovanillic acid esters as inhibitors of intestinal fatty acid uptake in differentiated Caco-2 cells

With raising prevalence of obesity, the regulation of human body fat is increasingly relevant. The modulation of fatty acid uptake by enterocytes represents a promising target for body weight maintenance. Recent results demonstrated that the trigeminal active compounds capsaicin, nonivamide, and trans-pellitorine dose-dependently reduce fatty acid uptake in differentiated Caco-2 cells as a model for the intestinal barrier. However, non-pungent alternatives have not been investigated and structural determinants for the modulation of intestinal fatty acid uptake have not been identified so far. Thus, based on the previous results, we synthesized 23 homovanillic acid esters in addition to the naturally occurring capsiate and screened them for their potential to reduce intestinal fatty acid uptake using the fluorescent fatty acid analog Bodipy-C12 in differentiated Caco-2 cells as an enterocyte model. Whereas pre-incubation with 100 μM capsiate did not change fatty acid uptake by Caco-2 enterocytes, a maximum inhibition of ?47% was reached using 100 μM 1-methylpentyl-2-(4-hydroxy-3-methoxy-phenyl)acetate. Structural analysis of the 24 structural analogues tested in the present study revealed that a branched fatty acid side chain, independent of the chain length, is one of the most important structural motifs associated with inhibition of fatty acid uptake in Caco-2 enterocytes. The results of the present study may serve as an important basis for designing potent dietary inhibitors of fatty acid uptake.

Synthesis and Evaluation of Orexin-1 Receptor Antagonists with Improved Solubility and CNS Permeability

Orexins are hypothalamic neuropeptides playing important roles in many functions including the motivation of addictive behaviors. Blockade of the orexin-1 receptor has been suggested as a potential strategy for the treatment of drug addiction. We have previously reported OX1 receptor antagonists based on the tetrahydroisoquinoline scaffold with excellent OX1 potency and selectivity; however, these compounds had high lipophilicity (clogP > 5) and low to moderate solubility. In an effort to improve their properties, we have designed and synthesized a series of analogues where the 7-position substituents known to favor OX1 potency and selectivity were retained, and groups of different nature were introduced at the 1-position where substitution was generally tolerated as demonstrated in previous studies. Compound 44 with lower lipophilicity (clogP = 3.07) displayed excellent OX1 potency (Ke = 5.7 nM) and selectivity (>1,760-fold over OX2) in calcium mobilization assays. In preliminary ADME studies, 44 showed excellent kinetic solubility (>200 μM), good CNS permeability (Papp = 14.7 × 10-6 cm/sec in MDCK assay), and low drug efflux (efflux ratio = 3.3).

Comparison of Phenylacetates with Benzoates and Phenylpropanoates as Antifeedants for the Pine Weevil, Hylobius abietis

This study concludes an extensive investigation of antifeedants for the pine weevil, Hylobius abietis (Coleoptera: Curculionidae), an economically important pest of planted conifer seedlings. Building on the previously reported antifeedant effects of benzoates and phenylpropanoids (aromatic compounds with one- or three-carbon-atom substituents on the benzene ring), we here report the antifeedant effects of compounds with two-carbon-atom side chains (i.e., phenylacetates). We also present new results; the best antifeedants from the benzoate class were tested at 10-fold lower concentrations in order to find the optimal antifeedants. Generally, for all three compound classes, efficient antifeedants were found to have one or two methyl, chloro, or methoxy substituents on the aromatic ring. For monosubstituted phenylpropanoids, the substituent preferably should be in the para-position. In the search for synergistic antifeedant effects among the three compound classes, combinations of compounds from the three classes were tested in binary and ternary mixtures.

TETRAHYDROPROTOBERBINE COMPOUNDS AND USES THEREOF IN THE TREATMENT OF NEUROLOGICAL, PSYCHIATRIC AND NEURODEGENERATIVE DISEASES

Tetrahydroprotoberbine (THPB) compounds and their use in the treatment of neurological, psychiatric and neurodegenerative diseases is provided. The compounds include d-govadine, l-govadine and racemic govadine, as well as d-THPBs of general formula (I). Enantioselective processes for preparing compounds of formula (I), and d- and l-govadine are also provided.(I)

Tyrosinase and Layer-by-Layer supported tyrosinases in the synthesis of lipophilic catechols with antiinfluenza activity

Catechol derivatives with lipophilic properties have been selectively synthesized by tyrosinase in high yield avoiding long and tedious protection/deprotection steps usually required in traditional procedures. The synthesis was effective also with immobilized tyrosinase able to perform for more runs. The novel catechols were evaluated against influenza A virus, that continue to represent a severe threat worldwide. A significant antiviral activity was observed in derivatives characterized by antioxidant activity and long carbon alkyl side-chains, suggesting the possibility of a new inhibition mechanism based on both redox and lipophilic properties.

Optimization of phenylacetic acid derivatives for balanced CRTH2 and DP dual antagonists

Our first generation CRTH2 and DP dual antagonists, represented by AMG 009, are more potent toward the CRTH2 receptor than to the DP receptor. Here we report our efforts in the discovery of CRTH2 and DP dual antagonists with more balanced potencies to both receptors, such as compound 15.

Light-Emitting Biomarker

The invention concerns novel 1,2-dioxetane derivatives of general formula (I) as defined in the description, capable of emitting a detectable luminescent signal, their use in a method for detecting and/or quantizing a physical, chemical or biological, in particular enzymatic, phenomenon, as well as a kit for implementing said method.

COMPOUNDS AND COMPOSITIONS AS PPAR MODULATORS

The invention provides compounds, pharmaceutical compositions comprising such compounds and methods of using such compounds to treat or prevent diseases or disorders associated with the activity of the Peroxisome Proliferator-Activated Receptor (PPAR) families.

CATALYTIC HYDROGENATION OF NITRILES TO PRODUCE CAPSAICINOID DERIVATIVES AND AMINE COMPOUNDS, AND METHODS FOR PURIFIYING AND OBTAINING THE POLYMORPHS THEREOF

Processes for preparing an amine compound by catalytically hydrogenating a precursor nitrile compound. In a particular aspect, the present hydrogenation process occurs in a dipolar organic solvent in the presence of a palladium/carbon catalyst and a strong anhydrous protic acid. In a further aspect, the preferred embodiment relates to a process for deprotecting a compound to produce an amine compound. In yet a further aspect, the preferred embodiment relates to amine products produced by the present processes. These amine products may be used for a variety of purposes.