20825-71-2

Usage

Uses

Used in Flavoring Industry:
3-Butenoic acid, 4-hydroxy-, gamma-lactone is used as a flavoring agent in food and beverages for its pleasant smell and taste, enhancing the sensory experience of consumers.
Used in Perfumery Industry:
3-Butenoic acid, 4-hydroxy-, gamma-lactone is utilized in the production of perfumes, where its sweet, coconut-like aroma contributes to the creation of various fragrances.
Used as a Chemical Intermediate:
3-Butenoic acid, 4-hydroxy-, gamma-lactone serves as a chemical intermediate for the synthesis of various organic compounds, playing a crucial role in the development of new chemical products.
Used in Pharmaceutical Research:
It has been studied for its potential biological activity, particularly as a precursor to the neurotransmitter gamma-aminobutyric acid (GABA) in the brain, which may have implications for the development of treatments for neurological disorders.

InChI:InChI=1/C4H4O2/c5-4-2-1-3-6-4/h1,3H,2H2

Upstream product

• 98-01-1 furfural 
• 4344-84-7 5-oxo-tetrahydro-furan-2-carboxylic acid 
• 497-23-4 2-buten-4-olide 
• 2363-83-9 ethylene-1,2-dicarbaldehyde 
• 135247-43-7 methyl 2,4-dihydroxybutanoate 
• 9004-34-6 cellulose 
• 61550-02-5 (furan-2-yloxy)-trimethylsilane 
• 2966-50-9 silver trifluoroacetate 

Downstream Products

• 23228-66-2 4-phenylhydrazono-butyric acid-(N'-phenyl-hydrazide) 
• 143302-97-0 2-(6-hydroxy-2,4,5-trimethoxybenzyl)-3-(3',4'-methylenedioxybenzoylpropane-1,3-dithiane)-γ-butyrolactone 
• 142836-54-2 2-(6-hydroxy-2,3,4-trimethoxybenzyl)-3-(3',4'-methylenedioxybenzoylpropane-1,3-dithiane)-γ-butyrolactone 
• 100921-72-0 furan-2-yl 2,2-dimethylpropanoate 
• 497-23-4 2-buten-4-olide 
• 107-02-8 acrolein 
• 181475-12-7 (R)-Benzo[1,3]dioxol-5-yl-[((4S,5S)-2,2-dimethyl-4-phenyl-[1,3]dioxan-5-yl)-methyl-amino]-((R)-5-oxo-tetrahydro-furan-3-yl)-acetonitrile 
• 402573-51-7 4-[(3-chloro-4-fluorophenyl)-amino]-6-cyclopentylmethoxy-7-{2-[4-(2-oxo-tetrahydrofuran-4-yl)-piperazin-1-yl]-ethoxy}-quinazoline 
• 2403-66-9 2-(3-hydroxypropyl)benzimidazole 
• 138958-26-6 5-[2-(3,4-Difluorophenyl)ethenyl]-2,2-dimethyl-3(2H)-furanone 
• 60736-96-1 1-p-fluorobenzyl-pyrrolidin-2-one 
• 96-48-0 4-butanolide 
• 5057-52-3 4-(2-chlorophenoxy)butanoic acid 
• 110-16-7 maleic acid 

Relevant academic research and scientific papers

DIMERIC IMMUNO-MODULATORY COMPOUNDS AGAINST CEREBLON-BASED MECHANISMS

Disclosed are small molecules against cereblon to enhance effector T cell function. Methods of making these molecules and methods of using them to treat various disease states are also disclosed.

Rearrangements and Tautomeric Transformations of Heterocyclic Compounds in Homogeneous Reaction Systems Furfural–Н2О2–Solvent

General information on the reactions of furfurals with hydrogen peroxide is given. We have discussed the Baeyer–Villiger rearrangement of furan 2-hydroxyhydroperoxides and tautomeric transformations with proton transfer of 2-hydroxyfuran and β-formylacrylic acid formed in a homogeneous reaction system furfural–Н2О2–solvent under the catalysis with the formed acids. The factors affecting these rearrangements and tautomeric transformations as well as their specificity in comparison with benzene type compounds, and the pathway of the reactions of furan aldehydes with Н2О2 in water have been analyzed. Ketoenol tautomerism of cyclic hemiacetal form of β-formylacrylic acid leading to its transformation into succinic anhydride has been described for the first time.

Synthesis of maleic and fumaric acids from furfural in the presence of betaine hydrochloride and hydrogen peroxide

Here we report the successful valorisation of furfural into maleic acid (MA) and fumaric acid (FA) with a total yield above 90% using an aqueous solution of betaine hydrochloride (BHC) in the presence of hydrogen peroxide. BHC can be recycled for at least 4 cycles and it can be used to directly convert xylose to MA and FA.

Pt nanoparticles over TiO2-ZrO2 mixed oxide as multifunctional catalysts for an integrated conversion of furfural to 1,4-butanediol

1,4-butanediol (BDO) is an important commodity chemical for manufacturing many basic chemicals and valuable polymers. Its current manufacturing processes are exclusively based on feedstocks derived from oil and natural gas. The biomass-to-BDO chemical transformation is via furfural, a key platform molecule from glucose and xylose. The integrated conversion involves two sequent reaction steps: selective oxidation of furfural to furanones and hydrogenation of the mixture of furanones to BDO. Platinum nanoparticles supported over TiO 2-ZrO2 perform well for both oxidation and hydrogenation steps and the total yield of BDO reaches 85.2%. The chemical composition and crystallinity of the mixed oxide support significantly affect the catalytic performance. The best catalyst is platinum supported over TiO 2-ZrO2 mixed oxide (Ti/Zr, 1:1) calcined at 823 K, which also exhibits good recoverability and recyclability in the five-run test.

Photolysis of butenedial at 193, 248, 280, 308, 351, 400, and 450 nm

We have studied the photolysis of butenedial at 193, 248, 280, 308, 351, 400, and 450 nm by using laser photolysis combined with cavity ring-down spectroscopy. The HCO radical is a photodissociation product at 193 and 248 nm. The corresponding HCO quantum yields are 0.55 ± 0.07 and 0.12 ± 0.01, independent of butenedial pressure and nitrogen buffer gas pressure. Absorption cross-sections of butenedial are (6.88 ± 0.39) × 10 -18 and (3.62 ± 0.69) × 10-19 cm2 at 193 and 248 nm. The end-products from the photolysis of butenedial at 193, 248, 308, and 351 nm were measured by FTIR. Acrolein and 3H-furan-2-one were observed and their yields have been estimated.

Interconversion and decomposition of furanones

The interconversion and decomposition of furan-2(3H)- and -2(5H)-one and their methylated derivatives were studied by following the changes in their photoelectron spectra during pyrolysis. Interconversion occurred at 300-400°C and decomposition at around 600°C giving CO and acrolein as the only products for the unsubstituted furanones. The experimental results suggest that decarbonylation takes place through the 2(3H) form as the common precursor.

Polymer pyrolysis and oxidation studies in a continuous feed and flow reactor: Cellulose and polystyrene

A dual-zone, continuous feed tubular reactor is developed to assess the potential for formation of products from incomplete combustion in thermal oxidation of common polymers. Solid polymer (cellulose or polystyrene) is fed continuously into a volatilization oven where it fragments and vaporizes. The gas-phase polymer fragments flow directly into a second, main flow reactor to undergo further reaction. Temperatures in the main flow reactor are varied independently to observe conditions needed to convert the initial polymer fragments to CO2 and H2O. Combustion products are monitored at main reactor temperatures from 400 to 850 °C and at 2.0-s total residence time with four on-line GC/FIDs; polymer reaction products and intermediates are further identified by GC/MS analysis. Analysis of polymer decomposition fragments at 400 °C encompasses complex oxygenated and aromatic hydrocarbon species, which range from high-molecular-weight intermediates of ca. 300 amu, through intermediate mass ranges down to C1 and C2 hydrocarbons, CO, and CO2. Approximately 41 of these species are positively identified for cellulose and 52 for polystyrene. Products from thermal oxidation of cellulose and polystyrene are shown to achieve complete combustion to CO2 and H2O at a main reactor temperature of 850 °C under fuel-lean equivalence ratio and 2.0-s reaction time. A dual-zone, continuous feed tubular reactor is developed to assess the potential for formation of products from incomplete combustion in thermal oxidation of common polymers. Solid polymer (cellulose or polystyrene) is fed continuously into a volatilization oven where it fragments and vaporizes. The gas-phase polymer fragments flow directly into a second, main flow reactor to undergo further reaction. Temperatures in the main flow reactor are varied independently to observe conditions needed to convert the initial polymer fragments to CO2 and H2O. Combustion products are monitored at main reactor temperatures from 400 to 850°C and at 2.0-s total residence time with four on-line GC/FIDs; polymer reaction products and intermediates are further identified by GC/MS analysis. Analysis of polymer decomposition fragments at 400°C encompasses complex oxygenated and aromatic hydrocarbon species, which range from high-molecular-weight intermediates of ca. 300 amu, through intermediate mass ranges down to C1 and C2 hydrocarbons, CO, and CO2. Approximately 41 of these species are positively identified for cellulose and 52 for polystyrene. Products from thermal oxidation of cellulose and polystyrene are shown to achieve complete combustion to CO2 and H2O at a main reactor temperature of 850°C under fuel-lean equivalence ratio and 2.0-s reaction time.

Prodrugs of benzenesulfonamide-containing COX-2 inhibitors

Prodrugs of COX-2 inhibitors are described as being useful in treating inflammation and inflammation-related disorders.

Preparation of chiral pyrrolidinone derivatives

A process for preparing a compound of formula IIa or IIb: STR1 wherein R2, R3, R4 and R5 independently represent hydrogen or C1 -C4 alkyl; and A is an optionally substituted aromatic or heteroaromatic ring system; the process comprising the steps of: (a) reacting a racemic mixture of a compound of formula II: STR2 wherein R2, R3, R4, R5 and A are as defined for formulae IIa and IIb; with a sterically hindered chiral esterifying agent to form enantiomers of formulae IIIa and IIIb: STR3 wherein R2, R3, R4, R5 and A are as defined for formulae IIa and IIb and R15 is a chiral sterically hindered residue; b) separating the diastereoisomers of formulae IIIa and IIIb; and (c) converting the diastereoisomers of formulae IIIa and IIIb separately to compounds of formulae IIa and IIb respectively by acid or base hydrolysis. If required, the unwanted enantiomer of formula IIa or IIb may be inverted to give the preferred isomer.