487-69-4

Usage

Uses

Used in Chemical Synthesis:
2,4-Dihydroxy-6-Methylbenzaldehyde is used as a raw material for chemical synthesis, particularly in the production of various organic compounds. Its presence of reactive groups such as phenols, aldehydes, and ketones allows for versatile chemical reactions, making it a valuable component in the synthesis of a wide range of products.
Used in Pharmaceutical Industry:
2,4-Dihydroxy-6-Methylbenzaldehyde is used as an intermediate in the synthesis of pharmaceutical compounds. Its unique structure and reactive groups enable the development of new drugs with potential therapeutic applications.
Used in Flavor and Fragrance Industry:
2,4-Dihydroxy-6-Methylbenzaldehyde is used as a flavoring agent and a fragrance ingredient in the food and cosmetics industries. Its aromatic properties contribute to the creation of distinct scents and flavors in various products.
Used in Dye and Pigment Industry:
2,4-Dihydroxy-6-Methylbenzaldehyde is used as a precursor in the production of dyes and pigments. Its chemical structure allows for the creation of a variety of colors, making it a valuable component in the development of new dyes and pigments for various applications.

InChI:InChI=1/C8H8O3/c1-5-2-6(10)3-8(11)7(5)4-9/h2-4,10-11H,1H3

Upstream product

• 504-15-4 orcinol 
• 50-00-0 formaldehyd 
• 74-90-8 hydrogen cyanide 
• 92114-96-0 mercury fulminate 
• 4435-90-9 3-formyl-4,6-dihydroxy-2-methyl-benzoic acid 
• 68-12-2 N,N-dimethyl-formamide 
• 67-66-3 chloroform 
• 557-21-1 zinc(II) cyanide 
• 859191-76-7 3-formyl-4,6-dihydroxy-2-methyl-benzoic acid ethyl ester 
• 2524-37-0 ethyl orselinate 
• 557-21-1 dicyanozinc 
• 2032-76-0 dichloromethyl-methyl sulfide 
• 527-55-9 4,5-dimethylresorcinol 

Downstream Products

• 101601-01-8 4-((Z)-2,4-dihydroxy-6-methyl-benzylidene)-2-phenyl-4H-oxazol-5-one 
• 10209-57-1 2,4-Diformyl-3,5-dihydroxytoluol 
• 10209-59-3 4,6-dihydroxy-2-methyl-isophthalaldehyde 
• 20050-76-4 7-hydroxy-5-methyl-3-phenyl-coumarin 
• 527-55-9 4,5-dimethylresorcinol 
• 767-81-7 2,3,5-trihydroxytoluene 
• 21236-14-6 benzoic acid-(2,4-dihydroxy-6-methyl-benzylidenehydrazide) 
• 346-51-0 7-hydroxy-5-methyl-2-p-tolyl-chromenylium; 2,4,6-trinitro-3-trifluoromethyl-phenolate 
• 34883-08-4 2-hydroxy-4-methoxy-6-methylbenzaldehyde 
• 34883-15-3 4-methoxy-3,6-dimethyl-2-hydroxybenzaldehyde 
• 83324-56-5 3-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-2,4-dihydroxy-6-methylbenzaldehyde 
• 83324-57-6 (E)-3-(3,7-dimethylocta-2,6-dien-1-yl)-4,6-dihydroxy-2-methylbenzaldehyde 
• 106325-72-8 3-chloro-2,4-dihydroxy-6-methyl-benzaldehyde 

Relevant academic research and scientific papers

SYNTHESIS OF COLLETOCHLORIN D

An efficient three-step synthesis of Colletochlorin D from orcinol has been achieved.

Synthesis, biological, and photophysical studies of molecular rotor-based fluorescent inhibitors of the trypanosome alternative oxidase

We have recently reported on the development and trypanocidal activity of a class of inhibitors of Trypanosome Alternative Oxidase (TAO) that are targeted to the mitochondrial matrix by coupling to lipophilic cations via C14 linkers to enable optimal interaction with the enzyme's active site. This strategy resulted in a much-enhanced anti-parasite effect, which we ascribed to the greater accumulation of the compound at the location of the target protein, i.e. the mitochondrion, but to date this localization has not been formally established. We therefore synthesized a series of fluorescent analogues to visualize accumulation and distribution within the cell. The fluorophore chosen, julolidine, has the remarkable extra feature of being able to function as a viscosity sensor and might thus additionally act as a probe of the cellular glycerol that is expected to be produced when TAO is inhibited. Two series of fluorescent inhibitor conjugates incorporating a cationic julolidine-based viscosity sensor were synthesized and their photophysical and biological properties were studied. These probes display a red emission, with a high signal-to-noise ratio (SNR), using both single- and two-photon excitation. Upon incubation with T. brucei and mammalian cells, the fluorescent inhibitors 1a and 2a were taken up selectively in the mitochondria as shown by live-cell imaging. Efficient partition of 1a in functional isolated (rat liver) mitochondria was estimated to 66 ± 20% of the total. The compounds inhibited recombinant TAO enzyme in the submicromolar (1a, 2c, 2d) to low nanomolar range (2a) and were effective against WT and multidrug-resistant trypanosome strains (B48, AQP1-3 KO) in the submicromolar range. Good selectivity (SI > 29) over mammalian HEK cells was observed. However, no viscosity-related shift could be detected, presumably because the glycerol was produced cytosolically, and released through aquaglyceroporins, whereas the probe was located, virtually exclusively, in the trypanosome's mitochondrion.

Synthesis of natural product-like polyprenylated phenols and quinones: Evaluation of their neuroprotective activities

Twenty-seven natural product-like polyprenylated phenols and quinones were synthesized and their neuroprotective activity was tested using human monoamine oxidase B (MAO-B) and SH-SY5Y cells. Eight compounds inhibited MAO-B (IC50 values 25 μM

Unusual polycyclic fused product by oxidative enzymatic dimerisation of 5-methylpyrogallol catalysed by horseradish peroxidase/H2O2

During investigations on the peroxidase-catalysed oxidation of polyhydroxylated monoaromatic substrates such as 5-methylpyrogallol, we observed a spectacular dimerisation proceeding by dearomatisation in contrast with most common reaction patterns involvi

Directed Remote Lateral Metalation: Highly Substituted 2-Naphthols and BINOLs by In Situ Generation of a Directing Group

A general synthesis of highly substituted 2-naphthols based on a new carbanionic reaction sequence is demonstrated. The reaction exploits the dual nature of lithium bases consisting of consecutive ring opening of readily available coumarins with either LiNEt2 or LiNiPr2 into Z-cinnamamides, thus generating a directing group in situ and allowing, by conformational freedom, a lateral directed remote metalation for ring closure to give the aryl 2-naphthols in good to excellent yields. These transformations can be combined to provide a more efficient one-pot process. Mechanistic insight into the remote lateral metalation step, demonstrating the requirement of Z-cinnamamide, is described. Application of this methodology to the synthesis of highly substituted 3,3′-diaryl BINOL ligands is also reported.

BORON-CONTAINING SMALL MOLECULES

Compounds, pharmaceutical formulations, and methods of treating bacterial infections are disclosed.

First total synthesis of kipukasin A

In this paper, a practical approach for the total synthesis of kipukasin A is presented with 22% overall yield by using tetra-O-acetyl-β-D-ribose as starting material. An improved iodine-promoted acetonide-forming reaction was developed to access 1,2-O-is

Synthesis and cytotoxic activities of novel 4-methoxy-substituted and 5-methyl-substituted (3′S,4′S)-(-)-cis-khellactone derivatives that induce apoptosis via the intrinsic pathway

This study deals with the design and synthesis of a series of novel 4-methoxy-substituted and 5-methyl-substituted (3′S,4′S)-(-)-cis-khellactones. The newly synthesized compounds were characterized by1H nuclear magnetic resonance (NMR),13

COMPOUNDS FOR USE AS INHIBITORS OF ALTERNATIVE OXIDASE OR CYTOCHROME BC1 COMPLEX

The invention provides compounds for use in inhibiting a microbial alternative oxidase (AOX) and/or cytochrome bc1 complex. The invention extends to the use of such inhibitors in agrochemicals and in pharmaceuticals, for treating microbial infe

The natural product brartemicin is a high affinity ligand for the carbohydrate-recognition domain of the macrophage receptor mincle

We demonstrate that the natural product brartemicin, a newly discovered inhibitor of cancer cell invasion, is a high-affinity ligand of the carbohydrate-recognition domain (CRD) of the C-type lectin mincle. Recent studies have revealed that mincle is a ke