14786-82-4

Usage

Uses

Used in Chemical Production:
4-methoxy-3-methylphenol is used as a precursor in the synthesis of various chemicals, most notably vanillin, a widely used flavoring agent. Its role in the production of vanillin is crucial, as it serves as a starting material for the creation of this popular flavor compound.
Used in Pharmaceutical Applications:
Guaiacol is utilized in the pharmaceutical industry for its potential antioxidant and anti-inflammatory properties. These characteristics make it a valuable compound for the development of medications aimed at treating conditions that involve oxidative stress and inflammation.
Used in the Food Industry:
In the food industry, 4-methoxy-3-methylphenol is employed as a preservative and flavoring agent. Its smoky flavor profile is particularly desirable in the production of smoked meats and cheeses, where it helps to impart a characteristic taste and aroma to these products.
Overall, 4-methoxy-3-methylphenol, or guaiacol, is a versatile compound with applications in chemical synthesis, pharmaceutical development, and food preservation and flavoring. Its distinctive properties and potential health benefits make it an important substance in these various fields.

InChI:InChI=1/C8H10O2/c1-6-5-7(9)3-4-8(6)10-2/h3-5,9H,1-2H3

Upstream product

• 18102-26-6 5-benzoyloxy-2-methoxy-toluene 
• 95-71-6 2-methylbenzene-1,4-diol 
• 77-78-1 dimethyl sulfate 
• 136-90-3 4-methoxy-3-methylaniline 
• 50741-92-9 2-methyl-4-nitroanisole 
• 186581-53-3 diazomethane 
• 2835-96-3 4-amino-2-methylphenol 
• 23438-17-7 4-methoxy-4-methylcyclohexa-2,5-dien-1-one 
• 13522-78-6 4-methoxy-3-methylphenyl acetate 
• 10024-90-5 4-methoxy-3-methylacetophenone 
• 24599-58-4 2,5-dimethoxy toluene 
• 14804-31-0 2-methyl-4-bromoanisole 
• 578-58-5 2-methylmethoxybenzene 
• 876-02-8 4-hydroxy-3-methylphenyl methyl ketone 

Downstream Products

• 105902-76-9 5-acetoxy-4-acetylamino-2-methoxy-toluene 
• 139016-11-8 (+/-)-trans-2-(3,4-dimethoxyphenyl)-2,3-dihydro-5-methoxy-3,6-dimethylbenzofuran 
• 13052-25-0 4-But-2-enyloxy-1-methoxy-2-methyl-benzol 
• 851096-55-4 (E)-1-methoxy-2-methyl-4-[(6-methylhepta-2,5-dien-1-yl)oxy]benzene 
• 74516-54-4 2-hydroxy-4-methyl-5-methoxybenzaldehyde 
• 123164-32-9 4-methoxycurcuphenol 
• 53939-66-5 acetic acid-(2,5-dimethoxy-4-methyl-anilide) 
• 34238-59-0 2,5-dimethoxy-4-methylaniline 
• 102014-97-1 acetic acid-(2-hydroxy-5-methoxy-4-methyl-anilide) 
• 21086-80-6 4-methoxy-5-methylbenzene-1,2-diol 
• 614-13-1 2-methoxy-5-methyl-1,4-benzoquinone 
• 1174528-02-9 C₂₀H₂₁NO₅ 
• 72054-83-2 4,4-dimethoxy-3-methylcyclohexa-2,5-dienone 
• 1326704-92-0 2,3-dihydro-5-methoxy-6-methyl-2-phenylbenzofuran 

Relevant academic research and scientific papers

Towards the rational design of novel charge-transfer materials: Biaryls with a dihedral angle-independent hole delocalization mechanism

Biaryl cation radicals are important electroactive materials, which show two mechanisms of hole delocalization: static delocalization at small interplanar dihedral angles and dynamic hopping at larger angles, reflecting the interplay between electronic coupling and structural reorganization. Herein, we describe the rational design of biaryls possessing an invariant hole delocalization mechanism.

Catalytic Asymmetric Total Synthesis of (+)- and (-)-Paeoveitol via a Hetero-Diels-Alder Reaction

The first catalytic asymmetric total synthesis of (+)- and (-)-paeoveitol has been accomplished in 42% overall yield via a biomimetic hetero-Diels-Alder reaction. The chiral phosphoric acid catalyzed hetero-Diels-Alder reaction showed excellent diastereo-

Fabricating Bifunctional Co?Al2O3@USY Catalyst via In-Situ Growth Method for Mild Hydrodeoxygenation of Lignin to Naphthenes

To enhance the catalytic activity and stability of metal catalysts in the hydrodeoxygenation of lignin derivatives into naphthenes, a bifunctional Co?Al2O3@USY catalyst was fabricated by the reduction of CoAl layered double hydroxide in-situ grown on the USY zeolite. In the hydrodeoxygenation of guaiacol, a 100.0 % conversion with cyclohexane yield up to 93.6 % was achieved at 180 °C, 3 MPa for 4 h, which should be the hitherto lowest reaction temperature that has been reported over Co-based metal catalysts. This catalyst was also relatively stable with 5 runs and exhibited excellent catalytic performance in the hydrodeoxygenation of other lignin model compounds and even real lignin feedstock into naphthenes. The high-efficiency of Co?Al2O3@USY was attributed to the synergistic effect between well-dispersed small Co nanoparticles and abundant acidic sites on the USY surface, while the outstanding stability was attributed to the anchoring effect of Al2O3 matrix to Co nanoparticles which avoided the leaching of Co species and particle agglomeration. This work provides a potential strategy for the design of an efficient and stable catalyst for lignin utilization.

Discovery of 5,6-Bis(4-methoxy-3-methylphenyl)pyridin-2-amine as a WSB1 Degrader to Inhibit Cancer Cell Metastasis

The gain of cell motility is an essential prerequisite for cancer metastasis. The ubiquitin ligase subunit WD repeat and SOCS box-containing 1 (WSB1) has been demonstrated to regulate hypoxia-driven tumor cell migration. However, there is still a lack of methods for discovering inhibitors targeting the WSB1 axis. Here, we employed phenotypic screening models and identified compound4that displayed migration inhibitory activity against WSB1-overexpressing cells. Further studies indicated that it may function as a WSB1 degrader, thus leading to the accumulation of the Rho guanosine diphosphate dissociation inhibitor 2 (RhoGDI2) protein, reversing the expression of downstream F-actin and formation of membrane ruffles, and disturbing the migration capacity of cancer cells. Moreover, compound4exhibited a promisingin vivoanticancer metastatic effects. Our findings show the discovery of a new WSB1 degrader, providing a unique solution for the treatment of cancer metastasis.

Synthetic method 4 - alkoxyphenol compounds

The invention discloses a synthetic method of 4 - alkoxyphenol compounds, and belongs to the field of organic chemical synthesis. The method is as follows: An aryl alkyl ether compound is added to the sealing tube. The catalyst dimerization acetic acid rhodium and the oxidizing agent iodobenzene diethyl ester are added, a solvent trifluoroacetic anhydride is added, and the 4 -alkoxyphenol compound is prepared by heating reaction. To the invention, high regioselectivity direct hydroxylation of the aryl alkyl ether compound is realized, the application range of the substrate is wide, the yield is high, the activity after amplification reaction does not significantly decay, and higher yield is still obtained. The utility model has good practicability and industrial application prospect.

Para -Selective hydroxylation of alkyl aryl ethers

para-Selective hydroxylation of alkyl aryl ethers is established, which proceeds with a ruthenium(ii) catalyst, hypervalent iodine(iii) and trifluoroacetic anhydride via a radical mechanism. This protocol tolerates a wide scope of substrates and provides a facile and efficient method for preparing clinical drugs monobenzone and pramocaine on a gram scale.

Palladium/Norbornene-Catalyzed Indenone Synthesis from Simple Aryl Iodides: Concise Syntheses of Pauciflorol F and Acredinone A

To show the synthetic utility of palladium/norbornene (Pd/NBE) cooperative catalysis, here we report concise syntheses of indenone-based natural products, pauciflorol F and acredinone A, which are enabled by direct annulation between aryl iodides and unsa

Synthesis of Highly Enantio-Enriched Heliespirones A and C by a Diastereoselective Aromatic Claisen Rearrangement

Computational methods were used to investigate the stereochemical course of the extra-annular Claisen rearrangement. The stereochemical fidelity of the synthetic strategy and comparison of the optical properties support the hypothesis that the heliespirones are scalemic natural products.

Tuning the Reactivity of Peroxo Anhydrides for Aromatic C-H Bond Oxidation

Phenol moieties are key structural motifs in many areas of chemical research from polymers to pharmaceuticals. Herein, we report on the design and use of a structurally demanding cyclic peroxide (spiro[bicyclo[2.2.1]heptane-2,4′-[1,2]dioxolane]-3′,5′-dione, P4) for the direct hydroxylation of aromatic substrates. The new peroxide benefits from high thermal stability and can be synthesized from readily available starting materials. The aromatic C-H oxidation using P4 exhibits generally good yields (up to 96%) and appreciable regioselectivities.

Biogenic synthesis of Fe2O3@SiO2 nanoparticles for ipso-hydroxylation of boronic acid in water

Here, biogenic synthesis of Fe2O3@SiO2 nanoparticles using fruit extract of Zanthoxylum rhetsa is reported. The SiO2 nanoparticles was synthesized using paddy straw which is a byproduct obtained in cultivation of rice. The composite was characterised by spectroscopic method like XRD, SEM, TEM and EDX analysis. The ipso-hydroxylation reactions were carried out with excellent yield within a moderate time period with mild reaction condition in all cases. Therefore, this approach may be considered as simple, easy, cheap and greener, environment friendly protocol for ipso-hydroxylation of arylboronic acids at 50 °C temperature.