73289-61-9

Upstream product

• 21893-97-0 2,6-bis(hydroxymethyl)-4-methoxyphenol 
• 129316-20-7 2,6-bis(bromomethylene)-4-methoxyphenol 
• 150-76-5 4-methoxy-phenol 
• 76-05-1 trifluoroacetic acid 
• 100-97-0 hexamethylenetetramine 
• 111171-20-1 2-hydroxy-3-(hydroxymethyl)-5-methoxybenzaldehyde 

Downstream Products

• 26230-27-3 4-hydroxy-5-methoxy-isophthalaldehyde-dioxime 
• 30070-60-1 4-methoxyphenol-2,6-dicarboxylic acid 
• 109486-06-8 2,5-dihydroxyisophthalaldehyde 
• 1440207-67-9 C₉H₉NO₄ 
• 1396316-18-9 S-(2,6-diformyl-4-methoxyphenyl) dimethylcarbamothioate 
• 129316-21-8 2,6-bis-1,4-dimethoxybenzene 
• 379668-70-9 4-methoxyphenol-2,6-dicarboxylic acid dichloride 
• 25224-72-0 1,4-dimethoxybenzene-2,6-dicarboxaldehyde 
• 129316-22-9 2,6-bis-1-hydroxy-4-methoxybenzene 

Relevant academic research and scientific papers

Design and synthesis of novel bis-hydroxychalcones with consideration of their biological activities

In the present study, eight new substituted bis-hydroxychalcones for the first time were designed, synthesized, purified and fully characterized. Then their inhibitory effects on the diphenolase activity of mushroom tyrosinase were evaluated. The concentration of compounds to scavenge 50% of ABTS (IC50) values were calculated for all the synthesized compounds. IC50 values for 2,2-azinobis (3-ethylbenzothiazoline-sulfonate) assay (ABTS) were in the range of 0.130–0.39?mM. Synthesized compounds possessed an inhibitory effect on tyrosinase activity, too. All of the products were much more active than E and C vitamins. The high antioxidant activity of products could be due to the longer conjugated system which can stabilize the free radical by resonance through a longer system. The concentration of compounds to scavenge 50% of LDOPA (IC50) values were in the range of 0.2–0.6?mM for the tyrosinase inhibition screening Products 4a, 4c, 4d, 4e and 4g which have inhibitory properties comparable to kojic acid (KA). Molecular modeling studies have been performed to achieve insight into the binding mode of the synthesized compounds to the tyrosinase enzyme active site.

Synthesis and study of new photochromic spiropyrans modified with carboxylic and aldehyde substituents

Three new photochromic spiropyrans containing a carboxylic group in the indoline fragment and an aldehyde substituent in the [2H]-chromene moiety were synthesized. The structure of the compounds obtained was studied using 1H and 13C NMR, IR and elemental analysis. Single crystal X-ray analysis was used to refine the molecular structure of 8′-formyl-1,3,3,6′-tetramethyl-spiro[indoline-2,2′-2H-chromene]-5-carboxylic acid. It was found out that in the solid state the molecules of that compound are arranged in dimeric associates due to the formation of intermolecular hydrogen bonds between carboxylic groups of two adjacent molecules. All the spiropyrans were shown to be photochromic with the lifetimes of the open forms in the range of 1.5–46.0 s.

Unexpected formation of a tubular architecture by optically active pure organic calixsalen

Herein, an unusual tubular formation of a supramolecular organic framework by optically active macrocyclic calixsalen is shown via single crystal X-ray diffraction. The monomers are either bound by hydrogen bonds between OH groups in the lower rim of the macrocycle to form an hourglass structure or form a capsule with the calixsalens arranged in a head-to-head motif.

Ratiometric detection of adenosine-5'-triphosphate (ATP) and cytidine-5'-triphosphate (CTP) with a fluorescent spider-like receptor in water

A series of water-soluble spider-like receptor molecules has been developed by the Schiff-base condensation of tris-(hydroxymethyl)aminomethane (TRIS) with various 2,6-diformylphenol (dfp) derivatives. The products were assessed for their anion sensing properties. Among these, the receptor with a methoxy substituent showed selective fluorescent sensing towards adenosine-5'-triphosphate (ATP) and cytidine-5'-triphosphate (CTP) in contrasting modes in 100% aqueous media at pH 7.2.

Readily prepared inclusion forming chiral calixsalens

Calixsalens, chiral triangular hexaimines are readily synthesized by [3 + 3] cyclocondensation of trans-(R,R)-1,2-diaminocyclohexane with 2-hydroxyisophthalaldehyde derivatives. The usually rigid calixsalen ring is able to invert its conformation as a consequence of steric repulsion between bulky substituents at the C5 positions of the aromatic rings. The steric and electronic nature of the substituents does not affect only the conformation of the macrocycle. Small polar substituents enforce dimeric self-association to form an apohost where each of the monomers simultaneously serves as the host and the guest of its partner. Non-associating calixsalens form assemblies in which two symmetry-related molecules are arranged in a head-to-head fashion to form a capsule, or unimolecular cages that are able to entrap solvent molecules in their intrinsic voids.

SOD activity and DNA binding properties of a new symmetric porphyrin Schiff base ligand and its metal complexes

4-Methoxy-2,6-bis(hydroxymethyl)phenol (1) was prepared from the reaction of 4-methoxyphenol and formaldehyde. The compound (1) was then oxidized to the 4-methoxy-2,6-diformylphenol (2) compound. Molecular structure of compound (2) was determined by X-ray

Ratiometric pH responsive fluorescent probes operative on ESIPT

A series of C-8′-oxime-appended spirobenzopyrans 4a-4d were synthesized and developed as fluorescent pH ratiometric probes operative in HEPES/ACN (8:2, v/v) buffer solutions. Acidochromic conversion of spirobenzopyran to merocyanine open form can facilita

Solid-state photochromism of 5-tert-butyl-2-hydroxyisophthalaldehyde

Colorless crystals of 5-tert-butyl-2-hydroxyisophthalaldehyde change to an orange-red color upon brief exposure to UV-vis radiation (λ> 300 nm). The colored crystals revert to colorless in the dark. X-ray diffraction revealed different packing patterns for the crystals of nonphotochromic and photochromic compounds.

Phenol-containing macrocyclic diamides as new catalysts in the highly regioselective conversion of epoxides to β-hydroxy thiocyanates

The regioselective ring-opening reactions of some epoxides with ammonium thiocyanate in the presence of a series of new phenol-containing macrocyclic diamides and also dibenzo-18-crown-6-, 18-crown-6-, benzo-15-crown-5-, and pyridine-containing macrocyclic diamide have been studied. The epoxides were subject to cleavage by NH4SCN in the presence of these catalysts under mild reaction conditions in various aprotic solvents. In this study, reagents and conditions have been discovered with which the individual β-hydroxy thiocyanates can be synthesized in high yield and with more than 90% regioselectivity. The results can be discussed in terms of a four-step mechanism: (1) formation of complex between catalyst and NH4SCN, (2) release of SCN- nucleophile from the complex, (3) reaction of the active nucleophile at the less sterically hindered site in the epoxide, and (4) regeneration of catalyst. The major advantages of this method are as follows: (1) high regioselectivity, (2) simple regeneration of catalyst, (3) its reuse through several cycles without a decrease in activity, and (4) ease of workup of the reaction.

Mono- and diformylation of 4-substituted phenols: A new application of the duff reaction

Careful control of the reaction conditions in a modified Duff reaction using anhydrous trifluoroacetic acid as the solvent enables the selective synthesis of either 4-substituted 2-formylphenols (5-substituted salicylaldehydes) or 4-substituted 2,6-diformylphenols in one step starting from commercially available 4-substituted phenols in moderate to good yield.