95-01-2

Usage

Uses

Used in Antioxidant Applications:
2,4-Dihydroxybenzaldehyde is used as an antioxidant agent for its ability to neutralize free radicals and prevent oxidative damage in various systems. Its potent antioxidative activity makes it a promising candidate for use in pharmaceutical, cosmetic, and food industries to protect against oxidative stress and extend shelf life.
Used in Antibacterial Applications:
In the field of microbiology and healthcare, 2,4-Dihydroxybenzaldehyde is utilized as an antibacterial agent. Its effectiveness in inhibiting bacterial growth contributes to the development of new antimicrobial treatments and products, such as disinfectants and preservatives.
Used in Chemical Synthesis:
2,4-Dihydroxybenzaldehyde is employed as an intermediate in the two-step synthesis of ethyl 3,5-dibromo-2,4-dihydroxycinnamate. This synthesis process highlights its utility in the production of specific chemical compounds, which can be further utilized in various industries, including pharmaceuticals and agrochemicals.

InChI:InChI=1/C7H6O3/c8-4-5-1-2-6(9)3-7(5)10/h1-4,9-10H

Upstream product

• 90-02-8 salicylaldehyde 
• 77287-34-4 formamide 
• 108-46-3 recorcinol 
• 864131-95-3 N,N'-diphenylformamidine 
• 68-12-2 N,N-dimethyl-formamide 
• 93-61-8 N-methyl-N-phenylformamide 
• 50-00-0 formaldehyd 
• 506-68-3 bromocyane 
• 74-90-8 hydrogen cyanide 
• 4082-08-0 7-hydroxy-2-(4'-hydroxyphenyl)benzopyrilium chloride 
• 67-66-3 chloroform 
• 10025-87-3 trichlorophosphate 
• 7722-84-1 dihydrogen peroxide 
• 7647-01-0 hydrogenchloride 

Downstream Products

• 673-22-3 2-Hydroxy-4-methoxybenzaldehyde 
• 613-45-6 2,4-Dimethoxybenzaldehyde 
• 19088-67-6 7-hydroxy-3-(phenylcarbonyl)-2H-chromen-2-one 
• 93-35-6 7-hydroxy-2H-chromen-2-one 
• 3477-69-8 (E)-N’-(2',4'-dihydroxybenzylidene)isonicotinohydrazide 
• 32396-77-3 (Z)-2-(2,4-dihydroxybenzylidene)-6-methoxybenzofuran-3(2H)-one 
• 30113-71-4 3-((Ξ)-2,4-dihydroxy-benzylidene)-chroman-2,4-dione 
• 107151-64-4 2-benzylamino-5-(2,4-dihydroxy-benzylidene)-thiazol-4-one 
• 102888-60-8 5-(2,4-diacetoxy-benzylidene)-3-(4-propoxy-phenyl)-thiazolidine-2,4-dione 
• 109565-44-8 (Z)-3-hydroxy-4-((5-oxo-2-phenyloxazol-4(5H)-ylidene)methyl)phenyl acetate 
• 6296-57-7 7-acetoxy-3-(3,4-dimethoxyphenyl)chromen-2-one 

Relevant academic research and scientific papers

Preparation of 2,4-dihydroxybenzaldehyde by the Vilsmeier-Haack reaction

An efficient synthesis of 2,4-dihydroxybenzaldehyde (1) from resorcinol via the Vilsmeier-Haack reaction has been developed. Either phosphorous oxychloride/DMF or oxalyl chloride/DMF produces 1 in yields of 65-75%. The intermediate formamidinium salts have been characterized.

Cytoplasmic Reactive Cationic Amphiphiles for Efficient Intracellular Delivery and Self-Reporting Smart Release

Nonviral gene delivery vectors need to overcome both extracellular and intracellular obstacles before releasing plasmid DNA in the transcriptionally active form. However, serum and transport stability desired for cationic polymer/pDNA polyplexes contradicts with the eventual plasmid release requirement; chain lengths of cationic polymer vectors render additional compromise between cytotoxicity and transfection efficiency. Although the introduction of stimuli-triggered degradable cationic polymers can partially solve these issues, the quest for novel design criteria and elucidation of elementary cellular transport pathways are highly desirable. Herein we report a supramolecular approach to construct fluorogenic gene delivery vectors via self-assembly of intracellular milieu-reactive cationic amphiphiles. This new type of micellar nanocarriers can effectively bind pDNA to form polyplexes due to multivalent cationic segments at micellar coronas. Upon cellular uptake and endosomal escape, hydrophobic micellar cores are subjected to fluorogenic Michael addition reactions with highly hydrophilic cytoplasmic thiols, leading to micellar disintegration, pDNA release, and emission turn-on for image-guided delivery. (Figure Presented).

Hydrogen-bonded supramolecular array in the crystal structure of ethyl 7-hydroxy-2-oxo-2h-chromene-3-carboxylate monohydrate

The crystal structure of ethyl 7-hydroxy-2-oxo-2H-chromene-3-carboxylate monohydrate (1), C12H10O5.H2O, was established by X-ray crystallographic analysis. The molecule of the title compound is essentially planar except for the carboxylate substituent group. The crystal packing supramolecular array arises from hydrogen bonds and intermolecular C-H...O=C contacts of the organic molecules and solvent water molecules, with graph-set descriptor)R24(8), R 21(6), R44(20)and5 (C) motifs. The water molecules are involved as donors and acceptors. The hydrogen bond and intermolecular interaction network is reinforced by stacking of the sheet through π-π interactions.

Coumarin-chalcone hybrids as inhibitors of MAO-B: Biological activity and in silico studies

Fourteen coumarin-derived compounds modified at the C3 carbon of coumarin with an α,β-unsaturated ketone were synthesized. These compounds may be designated as chalcocoumarins (3-cinnamoyl-2H-chromen-2-ones). Both chalcones and coumarins are recognized scaffolds in medicinal chemistry, showing diverse biological and pharmacological properties among which neuro-protective activities and multiple enzyme inhibition, including mitochondrial enzyme systems, stand out. The evaluation of monoamine oxidase B (MAO-B) inhibitors has aroused considerable interest as therapeutic agents for neurodegenerative diseases such as Parkinson’s. Of the fourteen chalcocumarins evaluated here against MAO-B, ChC4 showed the strongest activity in vitro, with IC50 = 0.76 ± 0.08 μM. Computational docking, molecular dynamics and MM/GBSA studies, confirm that ChC4 binds very stably to the active rMAO-B site, explaining the experimental inhibition data.

Three-Component Dynamic Covalent Chemistry: From Janus Small Molecules to Functional Polymers

A new multicomponent reaction involving 2-hydroxybenzaldehyde, amine, and 2-mercaptobenzaldehyde (HAM reaction) has been developed and applied to multicomponent polymerization and controlled radical polymerization for the construction of random and block copolymers. This chemistry features mild reaction conditions, high yield, simple isolation, and water as the only byproduct. With the advantages of the distinct nucleophilicity of thiol and hydroxyl groups, the chemistry could be used for stepwise labeling and modifications on primary amines. The Janus chemical joint formed from this reaction exhibits degradability in buffers and generates the corresponding starting reagents, allowing amine release. Interestingly, the chemical joint exhibits thermally activated reversibility with water as the catalyst. This multicomponent dynamic covalent feature has been applied to the metamorphosis of random and block copolymers, generating polymers with diverse architectures. This chemistry is expected to be broadly applicable to synthetic polymer chemistry and materials science.

Method for preparing 4-butyl resorcinol

The invention discloses a method for preparing 4-butyl resorcinol. The method comprises the following steps: (1) preparing 2, 4-dihydroxy benzaldehyde; (2) preparing 2, 4-dihydroxy benzylidene acetone; and (3) preparing the 4-butyl resorcinol. The method has the advantages as follows: firstly, raw materials and reagents used in the method are lower in toxicity, safer, cheaper, easier to obtain andconvenient to store, and the raw material cost and operation cost are greatly reduced; secondly, the method has few reaction steps, is convenient to operate, and is easier for large-scale production;and thirdly, high-toxicity three wastes are not generated, environmental pollution is reduced, and the ecological environment is protected. Meanwhile, the yield of the prepared product is high and can reach 90% or above.

Efficient microwave-assisted regioselective one pot direct: Ortho -formylation of phenol derivatives in the presence of nanocrystalline MgO as a solid base catalyst under solvent-free conditions

In this research, at first nanocrystalline MgO was prepared and then the solvent-free reactions of phenol derivatives with paraformaldehyde in the presence of the obtained nanocrystalline MgO as a new catalyst under microwave irradiation were investigated. In this reaction, ortho-hydroxyaromatic aldehydes were yielded as products. This method seems to be comparable with other reported methods due to its high yield and regioselectivity. The significant features of this method are short reaction times, high yields, and easy and quick isolation of the products.

Functional group manoeuvring for tuning stability and reactivity: Synthesis of cicerfuran, moracins (D, E, M) and chromene-fused benzofuran-based natural products

The protecting group manoeuvring as a strategy was applied for tuning the stability and reactivity of 4-(2,2-dibromovinyl)benzene-1,3-diol (12a) and 6-(2,2-dibromovinyl)-2,2-dimethylchroman-7-ol (22) in the domino synthesis of benzofuran-based natural products (1-8). The functional group demands and their impact on the reactivity driven by electronic effects were successfully managed by varying the protecting groups with substituted gem-dibromovinylphenols in domino couplings and triarylbismuth reagents under palladium-catalyzed conditions. This approach paved the way for the synthesis of moracin M (1) and cicerfuran (2), and the first time synthesis of moracin D (3) and moracin E (4) along with chromene-fused benzofuran-based natural products (5-8) in overall good yields.

Nitric oxide donor type coumarin derivatives, preparation methods therefor and medicinal use of nitric oxide donor type coumarin derivatives

The invention relates to the fields of pharmacochemistry and pharmacotherapeutics and particularly relates to nitric oxide donor type coumarin derivatives, preparation methods therefor and an application of the nitric oxide donor type coumarin derivatives. The compounds play a role in resisting tumors and can be applied to the preparation of antitumor drugs.

The first total synthesis of anemarchalconyn and anemarcoumarin A

Anemarchalconyn (1) and anemarcoumarin A (2), the natural bioactive compounds isolated from the rhizomes of Anemarrhena asphodeloides Bunge (Liliaceae), were first totally synthesized using easily available materials in short, convenient routes with overall yields of 32 and 48%.