74901-08-9

Usage

Uses

Used in Pharmaceutical Industry:
2-HYDROXY-5-HYDROXYMETHYL-BENZALDEHYDE is used as a potential precursor for the synthesis of other organic compounds, particularly in the development of new drugs or therapeutic agents. Its aromatic structure and hydroxyl groups allow for potential interactions with biological systems, making it a compound of interest for pharmaceutical applications.
Used in Cosmetic Industry:
In the cosmetic industry, 2-HYDROXY-5-HYDROXYMETHYL-BENZALDEHYDE is used as a fragrance ingredient due to its aromatic properties. Its presence in cosmetic products can contribute to the scent profile, enhancing the sensory experience for consumers.
Used in Food Industry:
2-HYDROXY-5-HYDROXYMETHYL-BENZALDEHYDE is used as a flavoring agent in the food industry, where its aromatic and functional groups can impart unique flavors to various food products.
Used as an Antioxidant:
Across various industries, 2-HYDROXY-5-HYDROXYMETHYL-BENZALDEHYDE is used as an antioxidant. Its hydroxyl groups provide the necessary functionality to neutralize free radicals, thereby preventing oxidation and extending the shelf life of products in which it is used.
Overall, 2-HYDROXY-5-HYDROXYMETHYL-BENZALDEHYDE's diverse potential applications and its presence in different industries highlight its versatility and the need for further study and exploration of its properties and uses.

InChI:InChI=1/C8H8O3/c9-4-6-1-2-8(11)7(3-6)5-10/h1-3,5,9,11H,4H2

Upstream product

• 90-02-8 salicylaldehyde 
• 635-93-8 5-chlorosalicyclaldehyde 
• 50-00-0 formaldehyd 
• 89-95-2 2-methyl-benzyl alcohol 
• 23731-06-8 5-(chloromethyl)salicylaldehyde 
• 20200-69-5 6-formyl-1',3',3'-trimethylspiro<2H-1-benzopyran-2,2'-<1H>-indole> 
• 3328-70-9 5-formyl-2-hydroxybenzaldehyde 
• 287398-51-0 C₂₀H₂₁NO₂ 

Downstream Products

• 3328-70-9 5-formyl-2-hydroxybenzaldehyde 
• 2206-43-1 4-methoxyisophthalic acid 
• 635-93-8 5-chlorosalicyclaldehyde 
• 871569-77-6 3-[2-(3-chlorophenyl)acetyl]-6-hydroxymethyl-2-oxo-2H-1-benzopyran-2-one 
• 787615-88-7 2-[2-(2-{2-[2-(2-formylphenoxy)ethoxy]ethoxy}ethoxy)ethoxy]-5-(hydroxymethyl)benzaldehyde 
• 883909-79-3 6-chloromethyl-2-oxo-2H-chromene-3-carboxylic acid 3-tert-butoxycarbonylamino-phenyl ester 
• 883909-78-2 6-chloromethyl-2-oxo-2H-chromene-3-carboxylic acid 4-tert-butoxycarbonylamino-phenyl ester 
• 883909-80-6 6-chloromethyl-2-oxo-2H-chromene-3-carboxylic acid 4-tert-butoxycarbonylamino-cyclohexyl ester 
• 883909-74-8 C₂₈H₃₀ClN₃O₈ 
• 883909-75-9 C₂₈H₃₀ClN₃O₈ 
• 329786-49-4 C₁₆H₁₇NO₃ 
• 1287714-75-3 5-[2-(1-adamantyl)-1H-indol-3-ylmethyl]-2-hydroxybenzaldehyde 
• 1379588-10-9 5-(1H-1,2,3-benzotriazol-1-ylmethyl)-2-hydroxybenzaldehyde 

Relevant academic research and scientific papers

Diazaborines Are a Versatile Platform to Develop ROS-Responsive Antibody Drug Conjugates**

Antibody–drug conjugates (ADCs) are a new class of therapeutics that combine the lethality of potent cytotoxic drugs with the targeting ability of antibodies to selectively deliver drugs to cancer cells. In this study we show for the first time the synthesis of a reactive-oxygen-species (ROS)-responsive ADC (VL-DAB31-SN-38) that is highly selective and cytotoxic to B-cell lymphoma (CLBL-1 cell line, IC50 value of 54.1 nM). The synthesis of this ADC was possible due to the discovery that diazaborines (DABs) are a very effective ROS-responsive unit that are also very stable in buffer and in plasma. DFT calculations performed on this system revealed a favorable energetic profile (ΔGR=?74.3 kcal mol?1) similar to the oxidation mechanism of aromatic boronic acids. DABs’ very fast formation rate and modularity enabled the construction of different ROS-responsive linkers featuring self-immolative modules, bioorthogonal functions, and bioconjugation handles. These structures were used in the site-selective functionalization of a VL antibody domain and in the construction of the homogeneous ADC.

A highly selective fluorescence and absorption sensor for rapid recognition and detection of Cu2+ ions in aqueous solution and film

A fluorescence and absorption chemosensor (SAAT) based on 5-(hydroxymethyl)-salicylaldehyde (SA) and o-aminothiophenol (AT) was designed and synthesized. SAAT in DMSO–HEPES (20.0 mM, v/v, 1:99, pH = 7.0) solution shows a highly selective and sensitive abs

Covalently functionalized carbon nanoparticles with a chiral Mn-Salen: A new nanocatalyst for enantioselective epoxidation of alkenes

A new protocol to obtain carbon nanoparticles (CNPs) covalently functionalized with a chiral Mn-Salen catalyst is described here. The new nanocatalyst (CNPs-Mn-Salen) was tested in the enantioselective epoxidation of some representative alkenes (CN-chromene, 1,2-dihydronaphthalene and cis-β-ethyl styrene), obtaining better enantiomeric excess values than that of the catalyst single molecule, highlighting the role of the nanostructure in the enantioselectivity.

Structural Identification of Products from the Chloromethylation of Salicylaldehyde

In the functionalization of salicylaldehyde to give 5-(chloromethyl)salicylaldehyde, two byproducts [5-(hydroxymethyl)salicylaldehyde and 5,5′-methylenebis(salicylaldehyde)] were also isolated. Detailed characterizations and structural analyses of all three products by single-crystal X-ray diffraction, multinuclear NMR spectroscopy, high-resolution mass spectrometry, and IR spectroscopic techniques are presented and discussed. A strategy is presented for the preferential isolation of the two byproducts through column chromatography.

Nerve Gas Simulant Sensing by a Uranyl–Salen Monolayer Covalently Anchored on Quartz Substrates

A uranyl complex monolayer that easily allows the optical detection of a nerve gas simulant, namely, dimethyl methylphosphonate, is reported. Both UV/Vis spectroscopy and photoelectron data confirm that the functional hybrid material coordinates a Lewis base by means of the P=O group, which interacts with the uranium equatorial site available for complexation.

Investigation of mechanism-based thrombin inhibitors: Implications of a highly conserved water molecule for the binding of coumarins within the S pocket

The synthesis of novel coumarins bearing on the lateral side chain in the 3-position an amine or a guanidine group is described. In vitro evaluation highlighted 14d which possesses a meta aniline side chain as a very potent THR inhibitor. Surprisingly, the introduction of a guanidine moiety always led to a decrease in THR inhibiting properties. We, thus, used docking experiments to rationalize the SAR in the series. This study showed the crucial role of a conserved water molecule in the specificity pocket of THR during docking simulation in order to explain the inactivity of guanidine derivatives.

3,6-Disubstituted coumarins as mechanism-based inhibitors of thrombin and factor Xa

In this work, coumarins were screened on thrombin (THR) and factor Xa (FXa), two of the most promising targets for the development of anticoagulant drugs. This allowed us to highlight compound 30, characterized by a 2,5-dichlorophenyl ester in the 3-position and a chloromethyl moiety in the 6-position, as a very potent THR inhibitor (ki/KI = 37 000 M-1 s-1). Moreover, this compound exhibits good selectivity over FXa (168-fold) and trypsin (54-fold). The mechanism of inactivation was investigated in this series and significantly differs from that previously observed with α-chymotrypsin. Indeed, the addition of hydrazine on the THR-inhibitor complex promotes a partial induced THR reactivation. This reactivation, confirmed by LC/MS, showed the resurgence of the native THR and a new dihydrazide complex. Docking experiments were then efficiently used to explain the trends observed in the enzymatic assays as well as to corroborate the postulated inhibition mechanism. Finally, the cell permeability of our derivatives was estimated using a computational approach.

COUMARIN DERIVATIVES, METHODS OF PREPARATION AND APPLICATION AND APPLICATION AS MEDICINES

The invention concerns compounds of general formula (I) in which: X, X' and X" independently of each other represent O or S; Y represents O, S, NH or NHS; R 3 represents in particular a cycloalkyl group; R 5, R 6, R 7 and R 8 mutually identical or different, represent in particular hydrogen; a halogen atom. Said compounds can be used as active substances of medicines as inhibitors of protease. "

Fischer's base as a protecting group: Protection and deprotection of 2- hydroxybenzaldehydes

The hydroxyl and aldehyde groups of 2-hydroxybenzaldehydes were protected by the reaction with Fischer's base and deprotected by the ozonolysis in methanol at -78°C to give the corresponding 2- hydroxybenzaldehydes in good to high yields. (C) 2000 Elsevier Science Ltd.