57439-16-4

Upstream product

• 16846-10-9 methyl 2,6-dihydroxy-4-methylbenzoate 
• 77-78-1 dimethyl sulfate 
• 186581-53-3 diazomethane 
• 480-67-1 2,6-dihydroxy-4-methyl-benzoic acid 
• 504-15-4 orcinol 
• 54130-89-1 2,6-dimethoxy-4-methyl-benzoic acid methyl ester 
• 67-56-1 methanol 
• 4860-88-2 4-hydroxy-7-methyl-2H,5H-pyrano[4,3-b]pyran-2,5-dione 
• 33176-11-3 2,7-dimethyl-4H-pyrano<3,2-c>-2H-pyran-4,5-dione 

Downstream Products

• 32743-99-0 3-formyl-2-hydroxy-6-methoxy-4-methyl-benzoic acid methyl ester 
• 205880-83-7 1-(2-Hydroxy-6-methoxy-4-methyl-phenyl)-2-methanesulfinyl-ethanone 
• 114561-50-1 acide hydroxy-2-methoxy-6-methyl-4-benzoique 

Relevant academic research and scientific papers

Design and Synthesis of Structure-Simplified Derivatives of Gonytolide for the Promotion of Innate Immune Responses

Gonytolide A (1), a dimeric chromanone substituted with the-lactone, shows promoting activity of innate immune responses. However, biological studies on this compound have been limited by the low amounts of 1 available from natural resources and the difficulty of its synthesis. In this study, we designed and synthesized structure-simplified gonytolide derivatives. Bischromone 10 and biflavone 13 both promoted the mammalian TNF-α signaling pathway and Drosophila innate immunity. They did not contain a chiral center and were easy to synthesize. Hence, they can be used as lead compounds for a new type of immunostimulating drugs and as research reagents.

RXR selective ligands

Novel nonatetraenoic acid derivatives which selectively bind to retinoic acid X-receptors (RXR) and which have anti-acne acitvity and which potentiate the activity of retinoids having RARα activity are disclosed.

The first synthesis of coniochaetones A and (±)-B: Two benzopyranone derivatives

An efficient synthesis of coniochaetone A and of racemate coniochaetone B was achieved by a short five-step procedure from methyl di-O-methyl-p-orsellinate. The key step is a cascade reaction of 2′-hydroxy-6′-methoxy-4′-methyl-2-(methylsulfinyl)- acetophenone with succindialdehyde in the presence of piperidine which allows the direct building of the tricyclic benzopyranone structure.

Reactions of fused and unfused α-pyrones with magnesium alkoxide, sodium alkoxide and water as the nucleophile: effects of chelation

The reactions between a series of α-pyrones (two mono- and three fused) and the non-chelating base sodium alkoxide, the chelating base magnesium alkoxide and water as the nucleophile, have been studied.Aromatic and other products formed reflect the points of attack on the pyrone systems and when sodium methoxide is used the ensuing cyclisation is preferentially by aldol mechanisms.The employment of excess magnesium methoxide or ethoxide gives magnesium-chelated precursors and the nature of products now depends on these intermediates, and the protection afforded by such magnesium chelation to the reaction products.In the case of structures containing chelated β-keto ester features the chelates are screened from attack as aldol acceptors, but are effective Claisen acceptors.In such chelates an adjacent methylene is activated by further magnesium alkoxide to act as an aldol or Claisen donor.These contrasting aldol/Claisen reactivities, as between a non-chelating and a chelating base, are illustrated in the ensuing chemistry of the pyrones.Treatment with water releases the main carbon chain with decarboxylation, from which new products may form.