57179-35-8

Usage

Uses

Used in Pharmaceutical Industry:
3-Methoxy-5-hydroxybenzaldehyde is used as an intermediate for the synthesis of various pharmaceutical compounds. Its ability to form a wide range of derivatives makes it a valuable building block in the development of new drugs with potential therapeutic applications.
Used in Flavor and Fragrance Industry:
3-Methoxy-5-hydroxybenzaldehyde is used as a key component in the creation of artificial vanilla flavoring. Its characteristic sweet, creamy, and slightly woody aroma is highly sought after in the food and beverage industry, as well as in the production of perfumes and cosmetics.
Used in Chemical Synthesis:
3-Methoxy-5-hydroxybenzaldehyde is used for the synthesis of Phenathrenes from cyclophanes. These complex organic molecules have potential applications in various fields, including materials science and medicinal chemistry, due to their unique structural and electronic properties.

Upstream product

• 97242-33-6 3-(chlorocarbonyl)-5-methoxyphenyl acetate 
• 7311-34-4 3,5-dimethoxybenzaldehdye 
• 67-56-1 methanol 
• 26153-38-8 3,5-dihydroxybenzaldehyde 
• 894077-48-6 3-[1,3]dioxolan-2-yl-5-methoxyphenol 
• 74-88-4 methyl iodide 
• 2150-44-9 1-carbomethoxy-3,5-dihydroxybenzene 
• 705-76-0 3,5-dimethoxybenzyl alcohol 
• 908609-54-1 N,N-diethyl 3-hydroxy-5-methoxybenzamide 
• 1972-28-7 diethylazodicarboxylate 
• 860562-81-8 3-methoxy-5-methoxycarbonyloxy-benzoic acid 
• 97242-30-3 3-acetoxy-5-methoxybenzoic acid 
• 19520-75-3 3-hydroxy-5-methoxybenzoic acid 
• 860590-75-6 3-methoxy-5-methoxycarbonyloxy-benzoyl chloride 

Downstream Products

• 1026977-55-8 3-Methoxy-5-[5-methyl-2-(4-trifluoromethyl-phenyl)-oxazol-4-ylmethoxy]-benzaldehyde 
• 197961-67-4 2-[3-(3-hydroxy-5-methoxyphenyl)-3-propenyl]-1,3-dioxane 
• 50637-29-1 3-(benzyloxy)-5-methoxybenzaldehyde 
• 398142-83-1 3-methoxy-5-(2-trimethylsilanylethoxymethoxy)benzaldehyde 
• 126809-66-3 (3-Methoxy-5-methoxymethoxy-phenyl)-methanol 
• 946001-79-2 3-formyl-5-methoxyphenyl trifluoromethanesulfonate 
• 1257518-08-3 C₁₁H₁₂O₃ 
• 960069-01-6 (E)-β-(5-methoxy-3-tert-butyldiphenylsilyloxyphenyl)-vinyl iodide 
• 960069-02-7 2-methylphenyl-E-(3-hydroxy-5-methoxy)-styryl ether 
• 960069-20-9 C₃₂H₃₄O₃Si 

Relevant academic research and scientific papers

Utilizing a copper-free Sonogashira reaction in the synthesis of the leukotriene a4 hydrolase modulator batatasin IV

Batatasin IV is a dihydrostilbenoid isolated from Chinese yams which was shown to have inhibitory activities against plant growth. Later studies showed that this compound may exhibit anti-inflammatory properties by inhibiting the epoxide hydrolase activity of the leukotriene A4 hydrolase enzyme. To access the dihydrostilbenoid skeleton, a copper-free SPhos-mediated Sonogashira reaction was conceived and the substrate scope was explored. Our results indicate that the reaction can tolerate the presence of free alcohols, aldehydes, nitro groups, and anilinyl groups. However, a substituent with an acidic phenol or carboxylic acid group gave significantly lower yields. Next, a total synthesis of batatasin IV was accomplished in 16% overall yield incorporating the reported copper-free Sonogashira reaction. Finally, we show that batatasin IV inhibits the hydrolysis of alanine p-nitroanilide by leukotriene A4 hydrolase with an IC50 of 91.4 μM.

Synthesis of Polysubstituted 3-Methylisoquinolines through the 6π-Electron Cyclization/Elimination of 1-Azatrienes derived from 1,1-Dimethylhydrazine

A convenient one pot microwave-assisted 6π-electron cyclization/aromatization approach toward 3-methylisoquinolines is reported. The starting 1-azatriene derivatives were prepared in situ by reaction of 2-propenylbenzaldehydes with 1,1-dimethylhydrazine, which exhibited superior performance when compared with other hydrazine derivatives. Minor amounts of the related 3,4-dihydro isoquinolines were formed concomitantly with the isoquinolines, and a mechanism for their generation was proposed. The reaction conditions were optimized, and its scope and limitations were explored. In general, the transformation proceeded in moderate to good yields.

A Chemical Disruptor of the ClpX Chaperone Complex Attenuates the Virulence of Multidrug-Resistant Staphylococcus aureus

The Staphylococcus aureus ClpXP protease is an important regulator of cell homeostasis and virulence. We utilized a high-throughput screen against the ClpXP complex and identified a specific inhibitor of the ClpX chaperone that disrupts its oligomeric sta

SKIN LIGHTENING COMPOUNDS

The present invention provides a compound of Formula I, II or III or a salt or prodrug derivative thereof that is a skin-lightening agent useful for the inhibition of melanin synthesis and/or the removal of existing melanin to function as a skin-lightening agent.

Synthesis and biological evaluation of novel gigantol derivatives as potential agents in prevention of diabetic cataract

As a continuation of our efforts directed towards the development of natural anti-diabetic cataract agents, gigantol was isolated from Herba dendrobii and was found to inhibit both aldose reductase (AR) and inducible nitric oxide synthase (iNOS) activity, which play a significant role in the development and progression of diabetic cataracts. To improve its bioefficacy and facilitate use as a therapeutic agent, gigantol (compound 14f) and a series of novel analogs were designed and synthesized. Analogs were formulated to have different substituents on the phenyl ring (compounds 4, 5, 8, 14a-e), substitute the phenyl ring with a larger steric hindrance ring (compounds 10, 17c) or modify the carbon chain (compounds 17a, 17b, 21, 23, 25). All of the analogs were tested for their effect on AR and iNOS activities and on D-galactose-induced apoptosis in cultured human lens epithelial cells. Compounds 5, 10, 14a, 14b, 14d, 14e, 14f, 17b, 17c, 23, and 25 inhibited AR activity, with IC50 values ranging from 5.02 to 288.8 μM. Compounds 5, 10, 14b, and 14f inhibited iNOS activity with IC50 ranging from 432.6 to 1188.7 μM. Compounds 5, 8, 10, 14b, 14f, and 17c protected the cells from D-galactose induced apoptosis with viability ranging from 55.2 to 76.26%. Of gigantol and its analogs, compound 10 showed the greatest bioefficacy and is warranted to be developed as a therapeutic agent for diabetic cataracts.

Substituted Pyran Derivatives

Certain 3,6-disubstituted and 2, 4, 5-trisubstituted pyran derivatives that exhibit potent activity on monoamine transport systems are provided. The 3, 6 and 2, 4, 5 pyrans are useful in probing the effects of their binding to monoamine transporter system

A practical in situ generation of the schwartz reagent. reduction of tertiary amides to aldehydes and hydrozirconation

A new, highly efficient in situ protocol (Cp2ZrCl2/LiAlH(OBu-t)3) is described for the generation of the Schwartz reagent which provides a convenient method for the amide to aldehyde reduction and the regioselective hydrozirconation-iodination of alkynes and alkenes. Highlighted are chemoselective reductions of benzamides derived by directed ortho metalation (DoM) chemistry, allowing the synthesis of valuable 1,2,3-substituted benzaldehydes. The single-step, three-component process proceeds in a very short reaction time, shows excellent functional group compatibility, and uses inexpensive and long-storage stable reducing reagents.

TREATMENT OF DISEASES BY EPIGENETIC REGULATION

The present disclosure provides non-naturally occurring polyphenol compounds that inhibit the bromodomain and extra terminal domain (BET) proteins. The disclosed compositions and methods can be used for treatment and prevention of diseases or disorders that are susceptible to administration of a BET inhibitor.

Schwartz Reagents: Methods of In Situ Generation and Use

Embodiments of the invention provide a method of using Schwartz Reagent, Cp2Zr(H)Cl, without accumulating or isolating it. Methods provide mixtures of Cp2ZrCl2, reductants that selectively reduce Cp2ZrCl2, and substrates. After reaction of Cp2ZrCl2 and the reductant, an intermediate reduction product is formed, apparently Schwartz Reagent. The in situ Schwartz Reagent then selectively reduces certain functional groups on the substrate. Substrates include tertiary amides, tertiary benzamides, aryl O-carbamates, and heteroaryl N-carbamates, which are reduced to aldehydes, benzaldehydes, aromatic alcohols, and heteroaromatics, respectively. Compared to prior methods, reagents are inexpensive and stable, reaction times are short, and reaction temperature in certain cases is conveniently room temperature. It has been estimated that using the in situ method described herein instead of synthesized or commercially obtained Schwartz Reagent provides a 50% reduction in cost.

3-AMINO-PYRAZOLO[3,4B]PYRIDINES USED AS INHIBITORS OF PROTEIN TYROSINE KINASES FOR TREATING ANGIOGENIC, HYPERPROLIFERATIVE OR NEURODEGENERATIVE DISEASES

The invention relates to compounds of general formula (I), in which R1 and R2 are described in the application, to the use of the compounds of general formula (I) as inhibitors of protein tyrosine kinases for treating various diseases, and to the compounds of general formulas (II) and (III) as intermediate compounds for producing compounds of general formula (I), in which X, R1a and R2a have the meanings as described in general formulas (II) and (III).