3272-11-5

Usage

Uses

Used in Polymer and Resin Synthesis:
Epoxysuccinic acid is utilized as a building block in the synthesis of various polymers and resins due to its ability to form strong bonds with other molecules, enhancing the durability and performance of the resulting materials.
Used in Pharmaceutical Development:
The unique chemical structure of epoxysuccinic acid makes it a promising candidate for the development of new pharmaceuticals, where its bonding capabilities can be leveraged to create innovative drug formulations.
Used in Adhesive Production:
Epoxysuccinic acid is employed as a key component in the production of adhesives, where its strong bonding properties contribute to the creation of effective and long-lasting adhesive products.
Used in Coating Formulation:
In the coatings industry, epoxysuccinic acid is used to formulate coatings with enhanced durability and bonding strength, thanks to its epoxy group's ability to form robust molecular connections.
Used in Agricultural Chemicals:
Epoxysuccinic acid is also utilized in the production of agricultural chemicals, where its bonding capabilities can improve the effectiveness and longevity of these products in various agricultural applications.
Overall, the versatility of epoxysuccinic acid, stemming from its unique chemical structure and bonding properties, positions it as a valuable compound across multiple industries, from pharmaceuticals and polymer synthesis to adhesives, coatings, and agricultural chemicals.

Upstream product

• 19071-25-1 (+/-)-2-chloro-3-hydroxy-succinic acid 
• 19071-26-2 β-bromo-dl-malic acid 
• 110-16-7 maleic acid 
• 110-17-8 (2E)-but-2-enedioic acid 
• 875758-12-6 fumaric acid ; bariumfumarate 
• 475-38-7 5,8-Dihydroxy-1,4-naphthoquinone 
• 23077-93-2 1,4,5,8-naphthalenediquinone 
• 75-91-2 tert.-butylhydroperoxide 
• 624-49-7 dimethylfumarate 
• 3291-46-1 (2SR,3SR)-oxirane-2,3-dicarboxylic acid diethyl ester 
• 17087-75-1 (-)-trans-2,3-oxiranedicarboxylic acid 
• 17015-08-6 (2R,3R)-oxirane-2,3-dicarboxylic acid 

Downstream Products

• 50-00-0 formaldehyd 
• 133-37-9 DL-tartaric acid 
• 87-69-4 tartaric acid 
• 15719-64-9 methylammonium carbonate 
• 16191-17-6 cis-2,3-epoxysuccinic anhydride 
• 17087-75-1 (-)-trans-2,3-oxiranedicarboxylic acid 
• 17015-08-6 (2R,3R)-oxirane-2,3-dicarboxylic acid 
• 6463-75-8 N-(DL-α-Methyl-benzyl)-erythro-β-hydroxy-DL-asparaginsaeure 
• 1186-90-9 erythro-β-hydroxy-DL-aspartic acid 
• 75-07-0 acetaldehyde 
• 3291-46-1 (2S,3S)-diethyl oxirane-2,3-dicarboxylate 
• 16417-32-6 N-benzyl-erythro-β-hydroxy-DL-aspartic acid 
• 3291-46-1 (2SR,3SR)-oxirane-2,3-dicarboxylic acid diethyl ester 
• 87-69-4 L-tartaric acid 

Relevant academic research and scientific papers

Degradation of the Cellulosic Key Chromophore 5,8-Dihydroxy-[1,4]-naphthoquinone by Hydrogen Peroxide under Alkaline Conditions

5,8-Dihydroxy-[1,4]-naphthoquinone (DHNQ) is one of the key chromophores in cellulosic materials. Its almost ubiquitous presence in cellulosic materials makes it a target molecule of the pulp and paper industry's bleaching efforts. In the presented study, DHNQ was treated with hydrogen peroxide under alkaline conditions at pH 10, resembling the conditions of industrial hydrogen peroxide bleaching (P stage). The reaction mechanism, reaction intermediates, and final degradation products were analyzed by UV/vis, NMR, GC-MS, and EPR. The degradation reaction yielded C1-C4 carboxylic acids as the final products. Highly relevant for pulp bleaching are the findings on intermediates of the reaction, as two of them, 2,5-dihydroxy-[1,4]-benzoquinone (DHBQ) and 1,4,5,8-naphthalenetetrone, are potent chromophores themselves. While DHBQ is one of the three key cellulosic chromophores and its degradation by H2O2 is well-established, the second intermediate, 1,4,5,8-naphthalenetetrone, is reported for the first time in the context of cellulose discoloration.

2, 3-Butanediamide Epoxide Compound and Preparation Method and Use Thereof

Provided are a compound of formula I which can be used as a drug against small RNA virus infections, and optical isomers, pharmaceutically acceptable salts, solvates or hydrates thereof. Also provided are the preparation method of the compound, the method for using the compound for treating bacterial infections and the use of the compound in the preparation of a drug for preventing and/or treating viral diseases caused by small RNA viruses.

Regioselective Cleavage of Electron-Rich Double Bonds in Dienes to Carbonyl Compounds with [Fe(OTf)2(mix-BPBP)] and a Combination of H2O2 and NaIO4

A method for the regioselective transformation of dienes to carbonyl compounds has been developed. Electron-rich olefins react selectively to yield valuable aldehydes and ketones. The method is based on the catalyst [Fe(OTf)2(mix-BPBP)] with an oxidant combination of H2O2 (1.0 equiv.) and NaIO4 (1.5 equiv.); it uses mild conditions and short reaction times, and it outperforms other olefin cleavage methodologies. The combination of an Fe-based catalyst, [Fe(OTf)2(mix-BPBP)], and the oxidants H2O2 and NaIO4 can discriminate between electronically different double bonds and oxidatively cleave the electron-rich bond in dienes to yield aldehydes and ketones in a regioselective manner. The reaction requires mild conditions (0-50 C) and short reaction times (70 min).

Design, synthesis, and screen of cathepsin K inhibitors

We synthesized a series of epoxysuccinic acid derivatives and evaluated their in vitro cathepsin K inhibitory activity The screening results show that the potency of compounds 9e, 9d, 9p, 9j and 9k (IC50 ≤ 0.005 μmol/L) were equal to or greater than that of the lead compound 9a. Less hydrophobic compounds showed weaker potency, which can be explained by the hydrophobic nature of the cathepsin K binding pockets.

Oxidation of some unsaturated acids by tetrakis (pyridine) silver dichromate: A kinetic and mechanistic study

The oxidation of a few unsaturated acids viz. maleic, fumaric, crotonic and cinnamic acids by tetrakis (pyridine) silver dichromate (TPSD) in dimethylsulphoxide (DMSO) leads to the formation of corresponding epoxide. The reaction is of first order with respect to TPSD and the acid. The reaction is catalysed by hydrogen ions. The hydrogen-ion dependence has the form : k obs = a + b [H+]. The oxidation of these acids was studied in nineteen different organic solvents. The solvent effect was analyzed by Kamlet's and Swain's multiparametric equations. Solvent effect indicated the importance of the cation-solvating power of the solvent. A mechanism involving a three-centre transition state has been postulated.

Design, Synthesis, and Evaluation of Aza-Peptide Epoxides as Selective and Potent Inhibitors of Caspases-1, -3, -6, and -8

Aza-peptide epoxides, a novel class of irreversible protease inhibitors, are specific for the clan CD cysteine proteases. Aza-peptide epoxides with an aza-Asp residue at P1 are excellent irreversible inhibitors of caspases-1, -3, -6, and -8 with second-order inhibition rates up to 1 910 000 M-1 s-1. In general, the order of reactivity of aza-peptide epoxides is S,S > R,R > trans > cis. Interestingly, some of the R,R epoxides while being less potent are actually more selective than the S,S epoxides. Our aza-peptide epoxides designed for caspases are stable, potent, and specific inhibitors, as they show little to no inhibition of other proteases such as the aspartyl proteases porcine pepsin, human cathepsin D, plasmepsin 2 from P. falciparum, HIV-1 protease, and the secreted aspartic proteinase 2 (SAP-2) from Candida albicans; the serine proteases granzyme B and α-chymotrypsin; and the cysteine proteases cathepsin B and papain (clan CA), and legumain (clan CD).

Kinetics and mechanism of oxidation of some unsaturated organic substrates by quinolinium chlorochromate

The oxidation of unsaturated organic compounds, viz. crotyl alcohol, allyl alcohol, crotonaldehyde and maleic acid by quinolinium chlorochromate (QCC) in acetic acid-water medium (50% v/v) leads to the formation of corresponding epoxide. The reaction is of first order each in QCC and the reductant. The reaction is catalysed by hydrogen ions. The increase in dielectric constant of the medium decreases the rate, while variation in ionic strength has no perceptible change in rate. The reaction rates have been determined at different temperatures and the activation parameters have been evaluated. The mechanism consistent with the observed results has been discussed.

Configuration and enantioselective synthesis of the fungal metabolite WF14861

A short enantioselective synthesis of the cathepsine inhibitor WF14861 (1) from the funghi Colletotrichum sp. as well as of its diasteroisomer 21 is presented. Comparison of the NMR data of the final products and, in particular, of the [α]D values of the intermediates allowed the confirmation of the formerly proposed structure 1. In addition, the so far unknown absolute configuration of all three stereogenic centres of WF14861 could be established by this synthesis.

Kinetics and mechanism of the oxidation of some unsaturated acids by quinolinium bromochromate

The oxidation of maleic, fumaric, crotonic and cinnamic acids by quinolinium bromochromate (QBC) in dimethylsulphoxide (DMSO) leads to the formation of corresponding epoxide. The reaction is of first order with respect to QBC and the acid. The reaction is catalysed by hydrogen ions. The hydrogen-ion dependence has the form: kobs = a + b [H+]. The oxidation of these acids was studied in nineteen different organic solvents. The solvent effect was analyzed by Kamlet's and Swain's multiparametric equations. Solvent effect indicated the importance of the cation-solvating power of the solvent. A mechanism involving a three-centre transition state has been postulated.

Aza-peptide epoxides: A new class of inhibitors selective for clan CD cysteine proteases

Aza-peptide epoxides, a new class of irreversible protease inhibitors, are specific for the clan CD cysteine proteases. The inhibitors have second-order rate constants up to 105 M-1 s-1, with the most potent epoxides having the S,S stereochemistry. The aza-Asn derivatives are effective legumain inhibitors, while the aza-Asp epoxides were specific for caspases. The inhibitors have little or no inhibition with other proteases such as chymotrypsin, papain, or cathepsin B.