2896-67-5

Usage

Uses

Used in Pharmaceutical Industry:
2-Methoxy-6-methylphenol is used as an active ingredient in pharmaceutical products for its antiseptic and expectorant properties. It is commonly found in cough syrups and throat lozenges, helping to alleviate symptoms of respiratory infections and promote easier breathing.
Used in Flavor and Fragrance Industry:
Guaiacol is used as a flavoring agent in foods and beverages, adding a unique taste and aroma to various products. Its distinct smell is also utilized in the creation of fragrances, contributing to the overall scent profile of perfumes, candles, and other scented items.
Used in Chemical Synthesis:
2-Methoxy-6-methylphenol serves as a precursor for the synthesis of other chemicals, including dyes and other organic compounds. Its versatility in chemical reactions makes it an essential component in the production of various chemical products.
Used in Manufacturing Industry:
Guaiacol is used in the manufacturing of various products, such as dyes and pharmaceuticals, due to its chemical properties and reactivity. Its presence in these industries highlights its importance in the production of a wide range of consumer and industrial goods.

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

Upstream product

• 148-53-8 3-methoxy-2-hydroxybenzaldehyde 
• 5034-74-2 5-bromo-3-methoxysalicylaldehyde 
• 488-17-5 3-methylbenzene-1,2-diol 
• 74-88-4 methyl iodide 
• 4463-33-6 1,2-dimethoxy-3-methylbenzene 
• 4383-05-5 2-hydroxy-3-methoxybenzyl alcohol 
• 104199-12-4 2-methoxy-6-(methoxymethyl)phenol 
• 123-73-9 trans-Crotonaldehyde 
• 86-51-1 2,3-dimethyoxybenzaldehyde 
• 67-56-1 methanol 
• 120-80-9 benzene-1,2-diol 
• 100-84-5 1-methoxy-3-methyl-benzene 
• 616-38-6 carbonic acid dimethyl ester 
• 90-05-1 2-methoxy-phenol 

Downstream Products

• 857009-39-3 2-methoxy-6-methyl-[1,4]benzoquinone-4-oxime 
• 32263-14-2 4-hydroxy-3-methoxy-5-methylbenzaldehyde 
• 488-17-5 3-methylbenzene-1,2-diol 
• 186743-33-9 6-methylallylguaiacol 
• 4463-33-6 1,2-dimethoxy-3-methylbenzene 
• 71233-03-9 1-(2-methoxy-6-methyl-phenoxy)-2,2,3r,4,4-pentamethyl-phosphetane 1c-oxide 
• 66495-65-6 2-methoxy-6-methyl-4-piperidin-1-ylmethyl-phenol 
• 611-68-7 2-methoxy-6-methyl-1,4-benzoquinone 
• 60632-42-0 2-methoxy-6-methylphenyl acetate 
• 37987-18-1 4-Hydroxy-3-methoxy-5-methyl-benzylalkohol 
• 93728-07-5 3,3'-Dimethoxy-4,4'-dihydroxy-5,5'-dimethyl-diphenyl-methan 
• 30151-75-8 1,10-Bis-(4-hydroxy-5-methoxy-3-methyl-benzoyl)-decan 
• 602-63-1 1,2-dihydroxy-3-methyl-anthraquinone 
• 86232-54-4 4-bromo-2-methoxy-6-methylphenol 

Relevant academic research and scientific papers

En Route to D-Ring Inverted Phorbol Esters

Phorbol esters are long regarded as tumor promotors, due to protein kinase C (PKC) activation, but more recently higher oxidized natural derivatives have been shown to display antitumor activity. Given the synthetic difficulty, systematic non-natural syst

Hollow, mesoporous, eutectic Zn1?xMgxO nano-spheres as solid acid-base catalysts for the highly regio-selectiveO-methylation of 1,2-diphenols

The highly regio-selectiveO-methylation of catechol with dimethyl carbonate (DMC), catalyzed by a solid acid-base catalyst, is an environmentally friendly chemical process for industrial production of guaiacol. However, a guaiacol yield below 84% and high reaction temperature above 280 °C limit its industrial application. Here, hollow, mesoporous Zn1?xMgxO nano-spheres with a eutectic structure, denoted as Zn1?xMgxO HMNSs (x= 0.012-0.089), are facilely fabricatedviathe calcination of Mg2+/Zn2+ion-adsorbing carbon spheres at 500 °C in air. In theO-methylation of catechol with DMC at 180 °C, Zn1?xMgxO HMNSs (x= 0.052) afford guaiacol in 95.5% yield with a complete catechol conversion. Furthermore, 89.0-95.3% mono-ether yields with high 1,2-diphenol conversions (94.5-100%) are also obtained for the other 1,2-diphenols bearing -CH3and -Br groups. Moreover, a plausible mechanism for highly selectiveO-methylation of catechol with DMC is proposed, in which the single-site activation and double-site activation of phenolic hydroxyls by the basic oxygen of Mg-O afford guaiacol and veratrole, respectively.

Preparation method of 5-methyl vanillin

The invention relates to a preparation method of 5-methyl vanillin, which comprises the following steps: 1) by using ortho vanillin as a raw material, carrying out hydrogenation reduction reaction under the action of a hydrogenation catalyst to obtain 6-m

Biomimetic Design of a 3 D Transition Metal/Carbon Dyad for the One-Step Hydrodeoxygenation of Vanillin

Enzyme catalysts always show an excellent catalytic selectivity, which is important in biochemistry, especially in catalytic synthesis and biopharming. This selectivity is achieved by combining the binding effect induced by the electrostatic effect of the enzyme to attract a specific substrate and then the prearrangement of the substrates inside the enzyme pocket. Herein, we report a proof-of-concept application of an interfacial electrostatic field induced by constructing Schottky heterojunctions to mimic the electrostatic catalysis of an enzyme. In combination with the 3 D structure, a transition metal/carbon dyad was designed by nanoconfinement methods to promote the differential binding effect and the space-induced organization of the reaction intermediate (vanillyl alcohol) to develop a new one-step hydrogenolysis of vanillin for the production of 2-methoxy-4-methylphenol with a remarkably high selectivity (>99 %).

Atomically Dispersed Co Catalyst for Efficient Hydrodeoxygenation of Lignin-Derived Species and Hydrogenation of Nitroaromatics

Single-atom catalysts (SACs) have attracted much attention due to their outstanding catalytic performance in heterogeneous catalysis. Here, we report a template sacrificial method to fabricate an atomically dispersed Co catalyst; three kinds of silica templates with different microstructures (MCM-41, SBA-15, and FDU-12) were employed and the effect of pore structure of the templates on the dispersity of Co was investigated. The catalysts fabricated with different templates presented different Co dispersities, leading to distinguishing catalytic performance. The optimized Co1?NC-(SBA) catalyst with atomically dispersed Co displayed outstanding catalytic activity for the hydrodeoxygenation (HDO) of lignin-derived species as well as the hydrogenation of various nitroaromatics. The reaction mechanism of the HDO of vanillin was investigated by using density functional theory calculations as well.

Structural features and antioxidant activities of Chinese quince (Chaenomeles sinensis) fruits lignin during auto-catalyzed ethanol organosolv pretreatment

Chinese quince fruits (Chaenomeles sinensis) have an abundance of lignins with antioxidant activities. To facilitate the utilization of Chinese quince fruits, lignin was isolated from it by auto-catalyzed ethanol organosolv pretreatment. The effects of three processing conditions (temperature, time, and ethanol concentration) on yield, structural features and antioxidant activities of the auto-catalyzed ethanol organosolv lignin samples were assessed individually. Results showed the pretreatment temperature was the most significant factor; it affected the molecular weight, S/G ratio, number of β-O-4′ linkages, thermal stability, and antioxidant activities of lignin samples. According to the GPC analyses, the molecular weight of lignin samples had a negative correlation with pretreatment temperature. 2D-HSQC NMR and Py-GC/MS results revealed that the S/G ratios of lignin samples increased with temperature, while total phenolic hydroxyl content of lignin samples decreased. The structural characterization clearly indicated that the various pretreatment conditions affected the structures of organosolv lignin, which further resulted in differences in the antioxidant activities of the lignin samples. These results can be helpful for controlling and optimizing delignification during auto-catalyzed ethanol organosolv pretreatment, and they provide theoretical support for the potential applications of Chinese quince fruits lignin as a natural antioxidant in the food industry.

Deoxyalkylation of guaiacol using haggite structured V4O6(OH)4

When V2O5 is used for the deoxygenation of guaiacol in methanol, it is reduced in situ to haggite structured V4O6(OH)4. Guaiacol prevents further reduction of the haggite phase in methanol and haggite catalyzes the partial deoxygenation of guaiacol. Haggite is a metastable redox catalyst for the deoxygenation of guaiacol, which follows the reverse Mars-van Krevelen mechanism. In addition, haggite is also a Lewis acid catalyst and catalyzes the alkylation of guaiacol with methanol as the alkylation reagent. The main products of the guaiacol deoxyalkylation are 2,6-dimethylphenol, 2-methoxy-6-methylphenol, 2,4,6-trimethylphenol, 2,3,6-trimethylphenol, 2,3,5,6-tetramethylphenol and 6-methyl-2-tert-butylphenol. Oligomerization takes place during the reaction but it is reversible. When the reaction is performed at 300 °C for 6 h, the 83.5% total selectivity for alkylphenols is achieved with a 99.0% conversion.

Examination of Selectivity in the Oxidation of ortho- and meta-Disubstituted Benzenes by CYP102A1 (P450 Bm3) Variants

Cytochrome P450 CYP102A1 (P450 Bm3) variants were used to investigate the products arising from the P450 catalysed oxidation of a range of disubstituted benzenes. The variants used all generated increased levels of metabolites compared to the wild-type enzyme. With ortho-halotoluenes up to six different metabolites could be identified whereas the oxidation of 2-methoxytoluene generated only two aromatic oxidation products. Addition of an ethyl group markedly shifted the selectivity for oxidation to the more reactive benzylic position. Epoxidation of an alkene was also preferred to aromatic oxidation in 2-methylstyrene. Significant minor products arising from the migration of one substituent to a different position on the benzene ring were formed during certain P450-catalysed substrate turnovers. For example, 2-bromo-6-methylphenol was formed from the turnover of 2-bromotoluene and the dearomatisation product 6-ethyl-6-methylcyclohex-2,4-dienone was generated from the oxidation of 2-ethyltoluene. The RLYF/A330P variant altered the product distribution enabling the generation of certain metabolites in higher quantities. Using this variant produced 4-methyl-2-ethylphenol from 3-ethyltoluene with ≥90 % selectivity and with a biocatalytic activity suitable for scale-up of the reaction.

The discovery of a novel route to highly substituted -tropolones enables expedient entry to the core of the gukulenins

A simple and general method for the synthesis of highly substituted α-tropolone ethers that allows rapid access to the bis(tropolone) core of the antiproliferative metabolites (-)-gukulenins A and F (3, 4) is described. The reaction proceeds by thermolyti

One-Pot Defunctionalization of Lignin-Derived Compounds by Dual-Functional Pd50Ag50/Fe3O4/N-rGO Catalyst

Generation of hydrogen from renewable sources and its safe utilization for efficient one-pot upgrading of renewable biofuels are a challenge. Bimetallic PdAg catalyst supported on Fe3O4/nitrogen-doped reduced graphene oxide (N-rGO) were synthesized for hydrogen generation from formic acid with high TOF (497 h-1 at 50 °C), and the hydrogen was subsequently utilized in situ for selective defunctionalization of lignin-derived chemicals with preserved aromatic nature at ambient pressure. Hydrodeoxygenation of aromatic aldehydes and ketones gave excellent yields (99% at 130 °C) with no use of additives. Furthermore, hydrogenolysis of β-O-4 and α-O-4 C-O model compounds produced only two products with high selectivity at 120 °C, which is an efficient and versatile one-pot platform for valorization of lignin biomass.