39657-47-1

Usage

InChI:InChI=1/C11H11ClO5/c1-6(13)17-10-8(15-2)4-7(11(12)14)5-9(10)16-3/h4-5H,1-3H3

Upstream product

• 118-41-2 Eudesmic acid 
• 530-57-4 3,5-dimethoxy-4-hydroxybenzoic acid 
• 6318-20-3 O-acetylsyringic acid 

Downstream Products

• 22802-00-2 1-(4-acetoxy-3,5-dimethoxy-phenyl)-2-diazo-ethanone 
• 63868-68-8 N-(4-Hydroxy-3,5-dimethoxybenzoyl)morpholine 
• 860743-02-8 2-(4-acetoxy-3,5-dimethoxy-benzoyl)-3-oxo-butyric acid ethyl ester 
• 53669-33-3 4-acetoxy-3,5-dimethoxybenzaldehyde 
• 52536-83-1 4-acetoxy-3,5-dimethoxy-benzoic acid amide 
• 134-96-3 syringic aldehyde 
• 50916-03-5 3-(4-acetoxy-3,5-dimethoxy-benzoyl)-oxazolidine 
• 50916-02-4 3-(4-acetoxy-3,5-dimethoxy-benzoyl)-thiazolidine 
• 50916-06-8 4-(4-acetoxy-3,5-dimethoxy-benzoyl)-thiomorpholine 
• 50916-01-3 3-(4-acetoxy-3,5-dimethoxy-benzoyl)-oxazolidin-2-one 
• 92432-61-6 N-<3,5-Dimethoxy-4-hydroxy-benzoyl>-N'-<δ-hydroxy-butyl>-guanidin 
• 99463-06-6 4-acetoxy-3,5-dimethoxybenzoic anhydride 
• 99463-05-5 (5'-formylfuran-2-yl)methyl 4-acetoxy-3,5-dimethoxybenzoate 
• 76534-73-1 2-<2-(4-acetoxy-3,5-dimethoxybenzamido)ethoxy>-1,1-diethoxyethane 

Relevant academic research and scientific papers

NOVEL α-TOCOPHEROL DERIVATIVES, AND COSMETIC USES OF THE SAME

The present invention relates to a novel andalpha;-tocopherol derivative compound and cosmetic uses thereof, more specifically, a compound represented by chemical formula 1. The present invention has an antioxidant activity as a novel compound and inhibits the activity of elastase, which is a degradation enzyme of elastin protein related to wrinkle formation of skin, thereby having an effect of alleviating skin wrinkles. In the chemical formula 1, n is 3, and R_1 is each independently hydrogen, a methyl group, or an acetyl group.COPYRIGHT KIPO 2019

NOVEL PHENOLIC ACID DERIVATIVES, AND USES OF THE SAME

The present invention relates to novel phenolic acid-type derivative compounds having whitening and antioxidant activities and a use thereof, and more specifically, to compounds represented by chemical formula 1, an isomer thereof, or a salt thereof. Compounds according to the present invention have skin-whitening activities suppressing tyrosinase, and thus may be beneficially used in skin-whitening pharmaceutical compositions or cosmetic products; and have anti-oxidant activities, and thus may be beneficially used in preventing or treating skin-aging. Herein, n is 0 or 1; X is NH or S; Y is C_1-C_2 alkyl; R_1 is benzyl, C_1-C_8 hydroxyalkyl, hydroxyaryl, hydroxyalkylaryl, an amino group, or an amide group; R_2 is H or C_1-C_3 alkyl; and R_3 is H or methyl.COPYRIGHT KIPO 2017

NOVEL PHENOLIC ACID DERIVATIVES, AND USES OF THE SAME

The present invention relates to a novel phenolic acid-type derivative compound having whitening and antioxidant activities and a use thereof, and more specifically, to a compound represented by chemical formula 1 below, an isomer thereof, or a salt thereof. Compounds according to the present invention have a tyrosinase-inhibiting skin whitening activity and therefore can be beneficially used in a skin-whitening pharmaceutical composition or cosmetic product, and also have an antioxidant activity and therefore can be used beneficially to prevent or treat skin aging. In the chemical formula 1, n is 0 or 1; X is NH or S; Y is an alkyl group having 1-2 carbon atoms; R is a hydroxyl alkyl, hydroxyl aryl, or hydroxyl alkylaryl group having 1-8 carbon atoms, an amino group, or an amide group; R_2 is H or an alkyl group having 1-3 carbon atoms; and R_3 is H or a methyl group.COPYRIGHT KIPO 2016

2-Diazo-1-(4-hydroxyphenyl)ethanone: A versatile photochemical and synthetic reagent

α-Diazo arylketones are well-known substrates for Wolff rearrangement to phenylacetic acids through a ketene intermediate by either thermal or photochemical activation. Likewise, α-substituted p-hydroxyphenacyl (pHP) esters are substrates for photo-Favorskii rearrangements to phenylacetic acids by a different pathway that purportedly involves a cyclopropanone intermediate. In this paper, we show that the photolysis of a series of α-diazo-p- hydroxyacetophenones and p-hydroxyphenacyl (pHP) α-esters both generate the identical rearranged phenylacetates as major products. Since α-diazo-p-hydroxyacetophenone (1a, pHP N2) contains all the necessary functionalities for either Wolff or Favorskii rearrangement, we were prompted to probe this intriguing mechanistic dichotomy under conditions favorable to the photo-Favorskii rearrangement, i.e., photolysis in hydroxylic media. An investigation of the mechanism for conversion of 1a to p-hydroxyphenyl acetic acid (4a) using time-resolved infrared (TRIR) spectroscopy clearly demonstrates the formation of a ketene intermediate that is subsequently trapped by solvent or nucleophiles. The photoreaction of 1a is quenched by oxygen and sensitized by triplet sensitizers and the quantum yields for 1a-c range from 0.19 to a robust 0.25. The lifetime of the triplet, determined by Stern-Volmer quenching, is 31 ns with a rate for appearance of 4a of k = 7.1 × 10 6 s-1 in aq. acetonitrile (1:1 v:v). These studies establish that the primary rearrangement pathway for 1a involves ketene formation in accordance with the photo-Wolff rearrangement. Furthermore we have also demonstrated the synthetic utility of 1a as an esterification and etherification reagent with a variety of substituted α-diazo-p- hydroxyacetophenones, using them as synthons for efficiently coupling it to acids and phenols to produce pHP protect substrates. The Royal Society of Chemistry and Owner Societies.

Factors influencing the antifolate activity of synthetic tea-derived catechins

Novel tea catechin derivatives have been synthesized, and a structure-activity study, related to the capacity of these and other polyphenols to bind dihydrofolate reductase (DHFR), has been performed. The data showed an effective binding between all molecules and the free enzyme, and the dissociation constants of the synthetic compounds and of the natural analogues were on the same order. Polyphenols with a catechin configuration were better DHFR inhibitors than those with an epicatechin configuration. Antiproliferative activity was also studied in cultured tumour cells, and the data showed that the activity of the novel derivatives was higher in catechin isomers. Derivatives with a hydroxyl group para on the ester-bonded gallate moiety presented a high in vitro binding to DHFR, but exhibited transport problems in cell culture due to ionization at physiologic pHs. The impact of the binding of catechins to serum albumin on their biological activity was also evaluated. The information provided in this study could be important for the design of novel medicinal active compounds derived from tea catechins. The data suggest that changes in their structure to avoid serum albumin interactions and to facilitate plasmatic membrane transport are essential for the intracellular functions of catechins.

Synthesis of selective butyrylcholinesterase inhibitors coupled between α-lipoic acid and polyphenols by using 2-(piperazin-1-yl)ethanol linker

In the previous paper (Bull. Korean Chem. Soc., 2011, 32, 2997), the hybrid molecules between a-lipoic acid (ALA) and polyphenols (PPs) connected with neutral 2-(2-aminoethoxy)ethanol linker (linker-1) showed new biological activity such as butyrylcholinesterase (BuChE) inhibition. In order to increase the binding affinity of the hybrid compounds to cholinesterase (ChE), the neutral 2-(2-aminoethoxy)ethanol (linker 1) was switched to the cationic 2-(piperazin-1-yl)ethanol linker (linker 2). The IC50 values of the linker-2 hybrid molecules for BuChE inhibition were lower than those of linker-1 hybrid molecules (except 9-2) and they also had the same great selectivity for BuChE over AChE (> 800 fold) as linker-1 hybrid molecules. ALA-acetyl caffeic acid (10- 2, ALA-AcCA) was shown as an effective inhibitor of BuChE (IC50 = 0.44 ± 0.24 μM). A kinetic study using 7- 2 showed that it is the same mixed type inhibition as 7-1. Its inhibition constant (Ki) to BuChE is 4.3 ± 0.09 μM.

Bioavailable diacylhydrazine ligands for modulating the expression of exogenous genes via an ecdysone receptor complex

The present invention relates to non-steroidal ligands for use in nuclear receptor-based inducible gene expression system, and a method to modulate exogenous gene expression in which an ecdysone receptor complex comprising: a DNA binding domain; a ligand binding domain; a transactivation domain; and a ligand is contacted with a DNA construct comprising: the exogenous gene and a response element; wherein the exogenous gene is under the control of the response element and binding of the DNA binding domain to the response element in the presence of the ligand results in activation or suppression of the gene.

Tricin from a Malagasy connaraceous plant with potent antihistaminic activity

The bioassay-guided separation of a Malagasy plant, Agelaea pentagyna, led to the isolation of a flavonoid, tricin (1), with potent inhibitory activity toward exocytosis from antigen-stimulated rat leukemia basophils (RBL-2H3). The structure-activity relationships among structurally related natural and synthetic flavonoids are also discussed.

Synthesis and structure-activity relationship of diarylamide derivatives as selective inhibitors of the proliferation of human coronary artery smooth muscle cells

A series of diarylamide derivatives were synthesized and evaluated for their inhibitory activities against human coronary artery smooth muscle cells (SMCs) and human coronary artery endothelial cells (ECs). Compound 2w was superior to the lead compound, Tranilast, in terms of the potency of the activity and cell selectivity.

Synthesis, gastrointestinal prokinetic activity and structure-activity relationships of novel N-[[2-(dialkylamino)ethoxy]benzyl]benzamide derivatives

Novel N-[[2-(dialkylamino)ethoxy]benzyl]benzamide derivatives (II-1-51), derived from the structural modification of metoclopramide (1), were synthesized and examined for their pharmacological activities. Among them, N-[4-[2-(dimethylamino)ethoxy]benzyl]-3,4-dimethoxybenzamide (II-34) which exhibited well balanced gastrointestinal prokinetic and antiemetic activities was selected as a new type of gastrointestinal prokinetic agent.