5438-54-0

Usage

Uses

Used in Flavoring and Fragrance Industry:
2,6-Dimethoxy-1-(allyloxy)benzene is used as a flavoring agent for its pleasant aroma and taste in food and beverages, enhancing the sensory experience of consumers.
Used in Perfumery and Cosmetics Industry:
Eugenol is used as a key ingredient in the production of perfumes, essential oils, and cosmetic products, contributing to their unique scents and properties.
Used in Dental Care Products:
2,6-Dimethoxy-1-(allyloxy)benzene is used as an antimicrobial agent in dental products such as mouthwashes and toothpastes, helping to maintain oral hygiene and prevent dental issues.
Used in Medicinal Applications:
Eugenol is studied for its potential medicinal properties and is used as an anti-inflammatory and analgesic agent, providing relief from pain and inflammation in various conditions.

InChI:InChI=1/C11H14O3/c1-4-8-14-11-9(12-2)6-5-7-10(11)13-3/h4-7H,1,8H2,2-3H3

Upstream product

• 91-10-1 1,3-dimethoxy-2-hydroxy-benzene 
• 106-95-6 allyl bromide 
• 107-05-1 3-chloroprop-1-ene 
• 35466-83-2 allyl methyl carbonate 
• 634-36-6 1,2,3-trimethoxybenzene 
• 959255-78-8 1,3-Dimethoxy-2-[((Z)-propenyl)oxy]-benzene 
• 71186-63-5 2-allyloxy-3-methoxy-phenol 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 6627-88-9 4-allyl-2,6-dimethoxyphenol 
• 225106-62-7 1-(4-acetoxy-3,5-dimethoxyphenyl)-2-bromopropane 
• 225106-61-6 1-(3,5-dimethoxy-4-hydroxyphenyl)-2-bromopropane 
• 835922-45-7 (S)-3-(3,4,5-trimethoxyphenyl)-1-O-tosyl-1,2-propanediol 
• 835922-47-9 (R)-3-(3,4,5-trimethoxyphenyl)-1-O-tosyl-1,2-propanediol 
• 835922-46-8 (R)-1-(3,4,5-trimethoxyphenyl)-2-propanol 
• 835922-48-0 (S)-1-(3,4,5-trimethoxyphenyl)-2-propanol 
• 638168-44-2 (R)-3-(3,4,5-trimethoxyphenyl)-1-O-benzoyl-2-O-(4-allyl-2,6-dimethoxyphenyl)-1,2-propanediol 
• 638168-46-4 (S)-3-(3,4,5-trimethoxyphenyl)-1-O-benzoyl-2-O-(4-allyl-2,6-dimethoxyphenyl)-1,2-propanediol 
• 638168-45-3 (R)-3-(3,4,5-trimethoxyphenyl)-1-O-benzoyl-1,2-propanediol 
• 638168-43-1 (S)-3-(3,4,5-trimethoxyphenyl)-1-O-benzoyl-1,2-propanediol 
• 638990-30-4 (R)-3-(3,4,5-trimethoxyphenyl)-1,2-propanediol 
• 638990-29-1 (S)-3-(3,4,5-trimethoxyphenyl)-1,2-propanediol 

Relevant academic research and scientific papers

Efficient demethylation of aromatic methyl ethers with HCl in water

A green, efficient and cheap demethylation reaction of aromatic methyl ethers with mineral acid (HCl or H2SO4) as a catalyst in high temperature pressurized water provided the corresponding aromatic alcohols (phenols, catechols, pyrogallols) in high yield. 4-Propylguaiacol was chosen as a model, given the various applications of the 4-propylcatechol reaction product. This demethylation reaction could be easily scaled and biorenewable 4-propylguaiacol from wood and clove oil could also be applied as a feedstock. Greenness of the developed methodversusstate-of-the-art demethylation reactions was assessed by performing a quantitative and qualitative Green Metrics analysis. Versatility of the method was shown on a variety of aromatic methyl ethers containing (biorenewable) substrates, yielding up to 99% of the corresponding aromatic alcohols, in most cases just requiring simple extraction as work-up.

Antibacterial mode of action of the daucus carota essential oil active compounds against campylobacter jejuni and efflux-mediated drug resistance in gram-negative bacteria

Today, an alarming rise of bacterial gastroenteritis in humans resulting from consuming Campylobacter-tainted foods is being observed. One of the solutions for mitigating this issue may be the antibacterial activity of essential oils. In the present research, we propose to study the antibacterial activity against Campylobacter and other Gram-negative bacteria of Daucus carota essential oil and its active molecules. In addition, a few chemically synthesized molecules such as (E)-methylisoeugenol, Elemicin, and eugenol were also studied. The results showed that the essential oil itself and its most active component, (E)-methylisoeugenol, exhibited bactericidal effects. Similar effects were detected using purified and chemically synthesized molecules. Also, it was observed that the Daucus carota essential oil and its active molecules affected intracellular potassium and intracellular ATP contents in Campylobacter cells. Inhibition of the membrane bound FO F1-ATPase was also observed. Eventually, for the first time, the efflux mechanism of active molecules of Daucus carota essential oil was also identified in gamma proteobacteria and its specific antibacterial activity against Campylobacter jejuni was associated with the lack of this efflux mechanism in this species.

Investigating the microwave-accelerated Claisen rearrangement of allyl aryl ethers: Scope of the catalysts, solvents, temperatures, and substrates

The microwave-accelerated Claisen rearrangement of allyl aryl ethers was investigated, in order to gain insight into the scope of the catalysts, solvents, temperatures, and substrates. Among the catalysts examined, phosphomolybdic acid (PMA) was found to greatly accelerate the reaction in NMP, at temperatures ranging from 220 to 300 °C. This method was found to be useful for preparing several intermediates previously reported in the literature using precious metal catalysts such as Au(I), Ag(I), and Pt(II). Additionally, substrates bearing bromo and nitro groups on the aryl portion required careful tailoring of the reaction conditions to avoid complex product profiles.

Modular synthesis of (E)-cinnamaldehydes directly from allylarenes via a metal-free DDQ-mediated oxidative process

An efficient synthesis of (E)-cinnamaldehydes by a metal-free DDQ-mediated oxidative transformation of allylarenes was developed. The protocol provides a practical method to prepare diverse (E)-cinnamaldehydes with broad functional group tolerance in good to excellent yields, including easy access to natural products randainal and geranyloxy sinapyl aldehyde from plant extracts. Finally, the mechanism of a single-electron transfer process was proposed.

Lignin depolymerization to monophenolic compounds in a flow-through system

A reductive lignocellulose fractionation in a flow-through system in which pulping and transfer hydrogenolysis steps were separated in time and space has been developed. Without the hydrogenolysis step or addition of trapping agents to the pulping, it is possible to obtain partially depolymerized lignin (21 wt% monophenolic compounds) that is prone to further processing. By applying a transfer hydrogenolysis step 37 wt% yield of lignin derived monophenolic compounds was obtained. Pulp generated in the process was enzymatically hydrolyzed to glucose in 87 wt% yield without prior purification.

Highly efficient Tsuji-Trost allylation in water catalyzed by Pd-nanoparticles

Palladium nanoparticles stabilized by poly(vinylpyrrolidone) catalyze Tsuji-Trost allylations in water with very high turnover numbers. The di-allylation of methylene active compounds and the allylation of bio-based phenols was performed in high yield. The allylation of lignin showed a high selectivity towards the phenolic OH groups.

Concise access toward chiral hydroxy phenylpropanoids: formal synthesis of virolongin B; kigelin; kurasoin A; 4-hydroxysattabacin, and actinopolymorphol A

A simple, two step strategy consisting of Sharpless asymmetric dihydroxylation followed by regioselective breaking of [Formula presented] bond is utilized to target key chiral intermediates of natural products virolongin B, kigelin, kurasoin A, 4-hydroxy-sattabacin, and actinopolymorphol A. Derivatives of enantiopure hydroxy phenyl propanoids and α-hydroxy Weinreb amides are synthesized. The reductive cleavage of [Formula presented] bond in a regioselective manner is obtained using Pd/C in methanol.

NOVEL 1-PHENYLMONO- OR -POLYHYDROXYPROPANE COMPOUNDS, COMPOSITIONS AND COSMETIC USES THEREOF

The present invention relates to novel compounds of formula (I) to compositions comprising same, and also to the use thereof for preventing and/or cosmetically treating the signs of aging of the skin.

Asymmetric glycolate alkylation approach towards total synthesis of 8-O.6′ and 8-O.4′-neolignans

The glycolate alkylation approach for the total synthesis of 8-O.6′ and 8-O.4′-neolignans has been optimized affording the natural products with high overall yields and excellent stereoselectivity. The developed approach can be further utilized towards the synthesis of many natural and unnatural neolignans. This is the first approach for the synthesis of neolignans using asymmetric glycolate alkylation approach.

A concise asymmetric synthesis of (-)-virolin, (-)-surinamensin,(-)- raphidecursinol B and (-)-polysphorin

Highly concise and general asymmetric syntheses of biologically important natural (-)-8,4-oxyneolignans [(-)-virolin, (-)-surinamensin, (-)-raphidecursinol B, and (-)-polysphorin] are reported. The key step in the synthesis is the Evan's syn-aldol reaction to achieve the adducts with the desired stereochemistry. The four biologically important plant metabolites were synthesized using two common intermediates. Georg Thieme Verlag Stuttgart · New York.