526-37-4

Usage

Uses

Used in Pharmaceutical Industry:
2,6-Dihydroxy-4-methylbenzaldehyde is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique chemical structure allows it to be a versatile building block for the development of new drugs with potential applications in treating various diseases.
Used in Chemical Synthesis:
In the field of chemical synthesis, 2,6-dihydroxy-4-methylbenzaldehyde is used as a key intermediate for the production of various organic compounds, including dyes, pigments, and polymers. Its reactivity and functional groups make it a valuable component in the synthesis of complex molecules.
Used in Process for Converting Atranol and its Derivatives:
2,6-Dihydroxy-4-methylbenzaldehyde is used in the process for converting atranol and its derivatives into hydrosoluble compounds. This application is particularly relevant in the fragrance and flavor industry, where hydrosoluble compounds are desired for their improved solubility and stability in various media.

Synthesis Reference(s)

Journal of the American Chemical Society, 70, p. 2120, 1948 DOI: 10.1021/ja01186a037

Contact allergens

Atranol has been identified as a potent and frequent allergen, occurring from the fragrance material oakmoss absolute, which is of botanical origin.

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

Upstream product

• 489-50-9 fumarprotocetraric acid 
• 521-39-1 salazinic acid 
• 6937-96-8 2,6-dimethoxy-4-methylbenzaldehyde 
• 479-20-9 atranorin 
• 34874-90-3 methyl haematommate 
• 479-25-4 acide formyl-3-dihydroxy-2,4-methyl-6-benzoique 
• 529-50-0 barbatolic acid 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 4179-19-5 1,3-dimethoxy-5-methylbenzene 
• 2524-37-0 ethyl orselinate 
• 126717-83-7 methyl 3-formyl-2,4-dimethoxy-6-methylbenzoate 
• 3187-58-4 methyl orsellinate 
• 82265-37-0 1,3-bis(methoxymethoxy)-5-methylbenzene 
• 504-15-4 orcinol 

Downstream Products

• 504-15-4 orcinol 
• 488-87-9 2,5-dimethyl-1,3-benzenediol 
• 480-67-1 2,6-dihydroxy-4-methyl-benzoic acid 
• 6937-96-8 2,6-dimethoxy-4-methylbenzaldehyde 
• 39503-23-6 hydroxy-2-methoxy-6-methyl-4-benzaldehyde 
• 609-25-6 5-methylpyrogallol 
• 20872-08-6 2,6-dimethoxy-4-methylbenzoic acid 
• 54130-89-1 2,6-dimethoxy-4-methyl-benzoic acid methyl ester 
• 61621-48-5 4,6-dibromo-2,5-dimethyl-resorcinol 
• 15918-52-2 trihydroxy-2,3,6-methyl-4-benzaldehyde 
• 4853-56-9 (butylidene)butylamine 

Relevant academic research and scientific papers

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

A novel 6-benzyl ether benzoxaborole is active against mycobacterium tuberculosis in vitro

We identified a novel 6-benzyl ether benzoxaborole with potent activity against Mycobacterium tuberculosis. The compound had an MIC of 2 μM in liquid medium. The compound was also able to prevent growth on solid medium at 0.8 μM and was active against intracellular bacteria (50% inhibitory concentration [IC50] 3.6 μM) without cytotoxicity against eukaryotic cells (IC50 100 μM). We isolated resistant mutants (MIC ≥ 100 μM), which had mutations in Rv1683, Rv3068c, and Rv0047c.

1 -HYDROXY-BENZOOXABOROLES AS ANTIPARASITIC AGENTS

Provided are compounds useful for controlling endoparasites both in animals and agriculture. Further provided are methods for controlling endoparasite infestations of an animal by administering an effective amount of a compound as described above, or a pharmaceutically acceptable salt thereof, to an animal, as well as formulations for controlling endoparasite infestations using the compounds described above or an acceptable salt thereof, and an acceptable carrier. The claimed compounds are described by the following Markush formula:A typical example for a compound according to above formula is: A typical example for a compound according to above formula is:

Chemical reactivity and skin sensitization potential for benzaldehydes: Can Schiff base formation explain everything?

Skin sensitizers chemically modify skin proteins rendering them immunogenic. Sensitizing chemicals have been divided into applicability domains according to their suspected reaction mechanism. The widely accepted Schiff base applicability domain covers aldehydes and ketones, and detailed structure-activity-modeling for this chemical group was presented. While Schiff base formation is the obvious reaction pathway for these chemicals, the in silico work was followed up by limited experimental work. It remains unclear whether hydrolytically labile Schiff bases can form sufficiently stable epitopes to trigger an immune response in the living organism with an excess of water being present. Here, we performed experimental studies on benzaldehydes of highly differing skin sensitization potential. Schiff base formation toward butylamine was evaluated in acetonitrile, and a detailed SAR study is presented. o-Hydroxybenzaldehydes such as salicylaldehyde and the oakmoss allergens atranol and chloratranol have a high propensity to form Schiff bases. The reactivity is highly reduced in p-hydroxy benzaldehydes such as the nonsensitizing vanillin with an intermediate reactivity for p-alkyl and p-methoxy-benzaldehydes. The work was followed up under more physiological conditions in the peptide reactivity assay with a lysine-containing heptapeptide. Under these conditions, Schiff base formation was only observable for the strong sensitizers atranol and chloratranol and for salicylaldehyde. Trapping experiments with NaBH3CN showed that Schiff base formation occurred under these conditions also for some less sensitizing aldehydes, but the reaction is not favored in the absence of in situ reduction. Surprisingly, the Schiff bases of some weaker sensitizers apparently may react further to form stable peptide adducts. These were identified as the amides between the lysine residues and the corresponding acids. Adduct formation was paralleled by oxidative deamination of the parent peptide at the lysine residue to form the peptide aldehyde. Our results explain the high sensitization potential of the oakmoss allergens by stable Schiff base formation and at the same time indicate a novel pathway for stable peptide-adduct formation and peptide modifications by aldehydes. The results thus may lead to a better understanding of the Schiff base applicability domain.

Synthesis of diverse analogues of Oenostacin and their antibacterial activities

Several diverse analogues of Oenostacin, a naturally occurring potent antibacterial phenolic acid derivative, have been synthesized. A small library with more than forty analogues having different aromatic rings and varied side chains has been achieved through solution phase synthesis. Some of these analogues, that is, 22, 23 and 42, possessed potent antibacterial activities against Staphylococcus epidermidis and Staphylococcus aureus having EC50 ranging from 0.49 to 0.67 μM as compared to Oenostacin (EC50 = 0.12 μM).

Synthese du virensate de methyle

The synthesis of methyl virensate (=methyl 4-formyl-3,8-dihydroxy-1,6,9-trimethyl-11-oxo-11H-dibenzodioxepin-7-carboxylate; 18) by the condensation of the substituted β-orcinol and orcinol units 9 and 10 followed by formylation and demethylation

Thermal Decomposition of Lichen Depsides

The thermal decomposition of the following lichen depsides has been described: lecanoric acid, gyrophoric acid, evernic acid, perlatolic acid, planaic acid, confluentic acid, atranorin, 4-O-demethylbarbatic acid, and sekikaic acid.Main reaction products are decarboxylated compounds, phenolic units, rearranged depsides, and xanthones.Triethylammonium salts of depside carboxylic acids decompose at reasonably lower temperature than the corresponding free acids. - Keywords: Lichen Depsides, Thermal Decomposition