326-58-9

Usage

Uses

Sesamol Acetate could be a useful for preparing antifungal agents.

InChI:InChI=1/C9H8O4/c1-6(10)13-7-2-3-8-9(4-7)12-5-11-8/h2-4H,5H2,1H3

Upstream product

• 533-31-3 Sesamol 
• 108-24-7 acetic anhydride 
• 75-36-5 acetyl chloride 
• 79-21-0 peracetic acid 
• 120-57-0 piperonal 
• 104-15-4 toluene-4-sulfonic acid 
• 64-19-7 acetic acid 
• 3162-29-6 1-(benzo[d][1,3]dioxol-6-yl)ethanone 
• 108-05-4 vinyl acetate 
• 108-22-5 Isopropenyl acetate 
• 274-09-9 Methylenedioxybenzene 

Downstream Products

• 66003-50-7 1-<4,5-(methylenedioxy)-2-hydroxyphenyl>ethanone 
• 7107-08-6 INV-75 
• 5460-53-7 1-acetoxy-2-bromo-4,5-methylenedioxybenzene 
• 96249-79-5 2'-hydroxy-4',5'-methylenedioxychalcone 
• 4424-13-9 6,7-methylenedioxy-2-phenyl-4H-benzopyran-4-one 
• 4388-66-3 6-phenyl-6,7-dihydro-8H-[1,3]dioxolo[4,5-g]chromen-8-one 
• 857982-72-0 3-hydroxy-1-(6-hydroxy-benzo[1,3]dioxol-5-yl)-3-phenyl-propan-1-one 
• 7107-10-0 4-hydroxy-5-nitro-1,2,methylenedioxybenzene 
• 6316-25-2 5-benzoyloxy-6-nitro-benzo[1,3]dioxole 
• 533-31-3 Sesamol 

Relevant academic research and scientific papers

An unexpected Pummerer rearrangement in the synthetic route to ethyl (2′-hydroxy-4′,5′-methylenedioxyphenyl)acetate: An alternative approach to 2,3-dimethylthio benzofurans

The synthesis of ethyl (2′-hydroxy-4′,5′-methylendioxophenyl)acetate, a fragment of the antihyperglycemic natural coumarin subcoriacin, is reported. We found an expeditious route to the title compound in five steps. Final metal catalyzed acid ethanolysis of the vinylic 1,1-methylthio methylsulfoxide derivative afforded the required aryl acetic ester, but in the absence of metal catalyst, an unexpected Pummerer rearrangement produced the 2,3-dimethylthiofuran derivative as the major product. This last result provides an alternative entry to 2,3-dimethlythiobenzofurans.

Modified methylenedioxyphenol analogs lower LDL cholesterol through induction of LDL receptor expression

Although statin therapy is a cornerstone of current low density lipoprotein (LDL)-lowering strategies, there is a need for additional therapies to incrementally lower plasma LDL cholesterol. In this study, we investigated the effect of several methylenedioxyphenol derivatives in regulating LDL cholesterol through induction of LDL receptor (LDLR). INV-403, a modified methylenedioxyphenol derivative, increased LDLR mRNA and protein expression in HepG2 cells in a dose- and time-dependent fashion. These effects were apparent even under conditions of HMG-CoA reductase inhibition. Electrophoresis migration shift assays demonstrated that INV-403 activates SREBP2 but not SREBP1c, with immunoblot analysis showing an increased expression of the mature form of SREBP2. Knockdown of SREBP2 reduced the effect of INV-403 on LDLR expression. The activation of SREBP2 by INV-403 is partly mediated by Akt/GSK3β pathways through inhibition of phosphorylation-dependent degradation by ubiquitin-proteosome pathway. Treatment of C57Bl/6j mice with INV-403 for two weeks increased hepatic SREBP2 levels (mature form) and upregulated LDLR with concomitant lowering of plasma LDL levels. Transient expression of a LDLR promoter-reporter construct, a SRE-mutant LDLR promoter construct, and a SRE-only construct in HepG2 cells revealed an effect predominantly through a SRE-dependent mechanism. INV-403 lowered plasma LDL cholesterol levels through LDLR upregulation. These results indicate a role for small molecule approaches other than statins for lowering LDL cholesterol. Copyright

Synthesis process 3,4 -methylenedioxy phenol

The invention relates to the technical field of compound synthesis, in particular to a synthesis process of 3,4 -methylenedioxy phenol, which comprises the following steps: 3,4 - methylenedioxy acetophenone. The second Catalyst, first solvent was added to the autoclave, and an oxidant was added, and reacted 25 - 50 °C under 4 - 8h, and the first solvent was separated and the solvent was separated. The resulting 3,4 -methylenedioxy phenol acetate is obtained. The second Solvent, sodium hydroxide solution was added to the autoclave, and reacted 20 - 60 °C at 2 - 6h, adjusted pH to 3-6 to obtain 3,4 - methylenedioxy phenol. The method solves the problems that 3,4 -methylenedioxy acetophenone in the prior art is low in yield and large in separation difficulty in preparation of sesame phenol. The process takes the pepper ring as the starting raw material and is divided into three-step reaction synthesis, the raw material conversion rate is high, no other side reaction is avoided, the reaction condition is mild, the production cost is low, and the product quality is better.

TRICYCLIC COMPOUNDS ACTING ON CRBN PROTEINS

The present invention discloses a series of tricyclic compounds and use thereof in preparing a medicament for treating a disease related to CRBN protein. Specifically, the present invention discloses a derivative compound of formula (1) or a pharmaceutically acceptable salt thereof.

Protection of COOH and OH groups in acid, base and salt free reactions

We report an iron-catalyzed general functional group protection method with inexpensive reagents. This environmentally benign process does not use acids or bases, and does not produce waste products. Further purification beyond filtration and evaporation is, in most cases, unnecessary. Free COOH and OH groups can be protected in a one-pot reaction.

First dual AK/GSK-3β inhibitors endowed with antioxidant properties as multifunctional, potential neuroprotective agents

The manuscript deals with the design, synthesis and biological evaluation of novel benzoxazinone-based and indole-based compounds as multifunctional neuroprotective agents. These compounds inhibit human adenosine kinase (hAK) and human glycogen synthase kinase 3 beta (hGSK-3β) enzymes. Computational analysis based on a molecular docking approach underlined the potential structural requirements for simultaneously targeting both proteins’ allosteric sites. In silico hints drove the synthesis of appropriately decorated benzoxazinones and indoles (5a-s, and 6a-c) and biochemical analysis revealed their behavior as allosteric inhibitors of hGSK-3β. For both our hit 4 and the best compounds of the series (5c,l and 6b) the potential antioxidant profile was assessed in human neuroblastoma cell lines (IMR 32, undifferentiated and neuronal differentiated), by evaluating the protective effect of selected compounds against H2O2 cytotoxicity and reactive oxygen species (ROS) production. Results showed a strong efficacy of the tested compounds, even at the lower doses, in counteracting the induced oxidative stress (50 μM of H2O2) and in preventing ROS formation. In addition, the tested compounds did not show any cytotoxic effect determined by the LDH release, at the concentration range analyzed (from 0.1 to 50 μM). This study allowed the identification of compound 5l, as the first dual hAK/hGSK-3β inhibitor reported to date. Compound 5l, which behaves as an effective antioxidant, holds promise for the development of new series of potential therapeutic agents for the treatment of neurodegenerative diseases characterized by an innovative pharmacological profile.

Tin-containing catalyst is used for a method of producing a calbonyl compd.

PROBLEM TO BE SOLVED: To provide a reaction catalyst having a high reaction selectivity and being recyclable in a peroxidation reaction using a carbonyl compound, and to provide a method for highly efficiently producing, for example, ester, lactone and formyloxy compounds or derivatives thereof by subjecting a carbonyl compound to a peroxidation reaction using the reaction catalyst.SOLUTION: A specific tin-containing catalyst can be used for a peroxidation reaction of a carbonyl compound, and a recyclable specific tin-containing catalyst is reusable for the reaction. A method for producing an oxide carries out a peroxidation reaction of a carbonyl compound in the presence of the tin-containing catalyst or the tin-containing recyclable catalyst.

The first vinyl acetate mediated organocatalytic transesterification of phenols: A step towards sustainability

The present report outlines our efforts toward a simple yet elegant protocol for O-acylation of a wide variety of phenols. This highly enabling and solventless method relies on vinyl acetate as an innocuous acyl donor and DABCO as an organocatalyst. Operational simplicity, excellent yields, higher and faster conversion rates without excess reagents, a simple workup and essentially no need of columns are some of the salient features of the reported protocol.

Tribromoisocyanuric acid (TBCA) as a mild and metal free catalyst for the acetylation and formylation of hydroxyl groups under solvent free conditions

A convenient approach for acetylation and formylation of various types of alcohols and phenols with acetic anhydride and formic acid in the presence of Tribromoisocyanuric acid (TBCA) as catalyst is reported. The reactions were carried out under solvent-free condition and in good to high yields at room temperature. This present method is featured with relatively mild reaction conditions, simple operation, broad substrate scope, clean work-up, short reaction times, good to high yields, excellent selectivity and also avoids tedious purifications and the use of toxic reagents.

Magnetically separable γ-Fe2O3 nanoparticles: An efficient catalyst for acylation of alcohols, phenols, and amines using sonication energy under solvent free condition

This paper reports a facile synthesis of magnetically separable iron oxide (γ-Fe2O3) nanoparticles using thermolysis method. The structural and morphological study of the synthesized γ-Fe2O3 nanoparticles was carried out using X-ray diffraction (XRD), field emission gun-scanning electron microscopy (FEG-SEM), energy dispersive X-ray spectrum (EDS), transmission electron microscopy (TEM), Fourier transform infrared spectroscopy (FT-IR), thermogravimetric analysis (TGA), and X-ray photoelectron spectroscopy (XPS) techniques. The electron microscopy reveals that the γ-Fe2O3 nanoparticles have spherical morphology with a particle size in the range of 40-100 nm. The XPS study confirmed the Fe is in +3 oxidation state. The synthesized γ-Fe2O3 nanoparticles have been used as an efficient heterogeneous catalyst for the organic transformation between phenols, alcohols, and amines with acetic anhydride under sonication using mild reaction conditions. Various electrons withdrawing and electrons donating substrates show an excellent yield of desired products with the advantage of magnetic separation and reusability of γ-Fe2O3 nanocatalyst.