458-35-5

Usage

Uses

Used in Pharmaceutical Industry:
CONIFERYL ALCOHOL is used as a fungal growth inhibitor for its ability to prevent the growth and proliferation of fungi, which can be beneficial in the development of antifungal medications and treatments.
Used in Plant Biology and Agriculture:
CONIFERYL ALCOHOL is used as a substrate in the biosynthesis of lignin, which is crucial for the structural integrity and defense mechanisms of plants. This application is vital in plant biology research and can contribute to the development of crops with enhanced resistance to pathogens and environmental stressors.
Used in Chemical and Material Science:
CONIFERYL ALCOHOL is used as a key intermediate in the synthesis of various lignin-based materials and products, such as biofuels, bioplastics, and other bio-based chemicals. Its role in the production of these sustainable materials makes it an important compound in the field of green chemistry and renewable resources.

Purification Methods

It is soluble in EtOH and insoluble in H2O. It can, however, be recrystallised from EtOH and distilled in a vacuum. It polymerises in dilute acid. The benzoyl derivative has m 95-96o (from pet ether), and the tosylate has m 66o. [Derivatives: Freudenberg & Achtzehn Chem Ber 88 10 1955, UV: Herzog & Hillmer Chem Ber 64 1288 1931, Beilstein 6 II 1093.]

InChI:InChI=1/C9H10O3/c10-5-1-2-7-3-4-8(11)9(12)6-7/h1-4,6,10-12H,5H2/b2-1+

Upstream product

• 1135-24-6 3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 63644-62-2 (E,E)-3-(4-hydroxy-3-methoxyphenyl)allyl 3-(4-hydroxy-3-methoxyphenyl)acrylate 
• 28028-62-8 ethyl ferulate 
• 20649-42-7 coniferaldehyde 
• 22329-76-6 methyl ferulate 
• 121-33-5 vanillin 
• 97-53-0 4-allylguaiacol 
• 3598-26-3 caffeoyl alcohol 
• 14031-35-7 S-Adenosyl-L-methionine 
• 485-80-3 S-adenosyl-L-methionine 
• 7382-59-4 guaiacylglycerol-β-guaiacyl ether 
• 9005-53-2 lignin 
• 37791-78-9 (2E)-3-(4-O-acetyl-3-methoxyphenyl)prop-2-en-1-yl acetate 
• 69017-41-0 (E)-3-(4-acetoxy-3-methoxyphenyl)-2-propen-1-ol 

Downstream Products

• 99-50-3 3,4-Dihydroxybenzoic acid 
• 2305-13-7 3-Guaiacylpropanol 
• 63644-71-3 (E)-4-(3-methoxy-1-propenyl)-2-methoxyphenol 
• 121-33-5 vanillin 
• 4263-87-0 (±)-trans-(E)-4-(3-(hydroxymethyl)-5-(3-hydroxyprop-1-en-1-yl)-7-methoxy-2,3-dihydrobenzofuran-2-yl)-2-methoxyphenol 
• 77550-11-9 4-cis,8-cis-bis(4-hydroxy-3-methoxyphenyl)-3,7-dioxabicyclo<3.3.0>octane-2,6-dione 
• 3810-34-2 4-endo-8-exo-bis-(4-hydroxy-3-methoxyphenyl)-3,7-dioxabicyclo<3.3.0>octan-2-one 
• 3810-34-2 4-cis,8-cis-bis(4-hydroxy-3-methoxyphenyl)-3,7-dioxabicyclo<3.3.0>octan-2-one 
• 487-36-5 (+/-)-pinoresinol 
• 76948-72-6 cleomiscosin A 
• 76948-72-6 cleomiscosin A 
• 76985-93-8 cleomiscosin B 
• 76985-93-8 (2S,3R)-3-(4-Hydroxy-3-methoxy-phenyl)-2-hydroxymethyl-10-methoxy-2,3-dihydro-1,4,5-trioxa-phenanthren-6-one 
• 74741-33-6 ethyl 2-(4-hydroxy-3-methoxyphenyl)-3-hydroxymethyl-1,4-benzodioxan-6-carboxylate 

Relevant academic research and scientific papers

Two-Step One-Pot Synthesis of Pinoresinol from Eugenol in an Enzymatic Cascade

The phytoestrogen pinoresinol is a high-value compound that has a protective effect against diverse health disorders, and thus is of interest for the pharmaceutical industry. Isolation of pinoresinol from plants suffers from low yields, and its chemical synthesis involves several work-up steps. In this study we devised a novel two-step one-pot enzymatic cascade combining a vanillyl-alcohol oxidase and a laccase for the production of pinoresinol from eugenol via the intermediate coniferyl alcohol. Along with the well-characterized vanillyl-alcohol oxidase from Penicillium simplicissimum used to catalyze the oxidation of eugenol, enzyme screening revealed three bacterial laccases that were appropriate for the synthesis of pinoresinol from coniferyl alcohol. The cascade was optimized regarding enzyme ratios, pH value, and the presence of organic solvents. Under optimized conditions, pinoresinol concentration achieved 4.4 mM (1.6 gl-1), and this compound was isolated and analyzed. Increasing value: The high-value compound pinoresinol is synthesized in a two-step one-pot process combining the vanillyl-alcohol oxidase from Penicillium simplicissimum (PsVAO) and a bacterial laccase starting from the inexpensive substrate eugenol. tBME=tert-butyl methyl ether.

Allylation of a lignin model phenol: A highly selective reaction under benign conditions towards a new thermoset resin platform

The lack of aromatic material constituents derived from renewable resources poses a problem to meet the future demands of a more sustainable society. Lignin is the most abundant source of aromatic structures found in nature and is a highly interesting source for material applications. Development of controlled chemical modification routes of lignin structures are crucial in order to further develop this area. In this study allyl chloride is used to selectively modify a lignin phenol in the presence of other lignin functionalities, i.e. aliphatic hydroxyls and conjugated alkenes, under mild reaction conditions in quantitative yields. For this, coniferyl alcohol was used as a model compound in the present study. The modification was carried out in ethanol as the synthesis media. Studies on the effect of reaction time and temperature revealed optimum conditions allowing for a quantitative yield without any detectable levels of byproducts as studied with NMR, FT-IR and FT-Raman. The thermal stability of the formed product was determined to be up to at least 160 °C through DSC measurements. In addition, as a proof of concept, the use of the allylated monomer to form crosslinked films using free radical thiol-ene polymerization was demonstrated.

On the role of the monolignol γ-carbon functionality in lignin biopolymerization

In order to investigate the importance of the monomeric γ-carbon chemistry in lignin biopolymerization and structure, synthetic lignins (dehydrogenation polymers; DHP) were made from monomers with different degrees of oxidation at the γ-carbon, i.e., carb

COMPOUNDS HAVING HEPATIAL DISEASE EFFECTIVE

The invention discloses a compound with a hepatopathy curative effect, and the compound is a compound shown as a general formula (I), an optical isomer or pharmaceutically acceptable salt thereof, canbe applied to treatment or prevention of hepatopathy, particularly to drugs for treating or preventing fatty liver, liver fibrosis or liver cirrhosis, and has a good application prospect.

Non-plasmonic Ni nanoparticles catalyzed visible light selective hydrogenolysis of aryl ethers in lignin under mild conditions

Light-driven catalysis on catalytically versatile group VIII metals, which has been widely used in thermal catalysis, holds great potential in solar-to-chemical conversion. We report a novel photocatalysis process for the selective hydrogenolysis of aryl ethers in lignin on a heterogeneous catalyst of non-precious Ni nanoparticles supported on ZrO2. Three aryl ether bonds in lignin were successfully cleaved under mild conditions with excellent conversion and good to excellent selectivity under visible light irradiation. We also used solar irradiation to demonstrate a significant reduction in the total energy consumption. The light irradiation excited interband transitions in Ni nanoparticles and the resultant energetic electrons enhanced the activity of reductive cleavage of the aryl ethers. Its application potential was illustrated by the depolymerization of dealkaline lignin to give a total monomer yield of 9.84 wt% with vanillin, guaiacol, and apocynin as the three major products.

Improved Pd/Ru metal supported graphene oxide nano-catalysts for hydrodeoxygenation (HDO) of vanillyl alcohol, vanillin and lignin

Pd and Ru nanoparticles supported on graphene oxide (GO) [Pd?GO and Ru?GO] and bimetallic [Pd/Ru?GO] were prepared and well characterized by XRD, FT-IR, EDS, TEM, XPS and ICP-AES analyses. The prepared nano-catalysts were tested for hydrodeoxygenation (HDO) of lignin monomer molecules-vanillyl alcohol and vanillin. In comparison with previously reported methods, Ru?GO and bimetallic Pd/Ru?GO catalysts showed high activity and selectivity, under milder conditions, at room temperature and 145 psi H2 pressure, for the formation of p-creosol, a value added product, as a potential future biofuel with antibacterial and anti-insecticidal properties. The multifold advantages of both these catalysts are in terms of reduced catalyst loading with a lower metal content and ambient temperture conditions resulting in higher conversion of the starting material. Furthermore, the efficacy of the developed methodology using Ru?GO and bimetallic Pd/Ru?GO catalysts under the optimized conditions was tested on the phenolic components of commercial lignin obtained by photo-catalytic fragmentation using TiO2, to obtain a mixture after HDO which contained vanillyl alcohol and p-creosol among others, as indicated by HPLC-MS analysis.

METHOD OF FORMING MONOMERS AND FURFURAL FROM LIGNOCELLULOSE

The present disclosure relates to a method of producing monophenolicmonomers and furfural from lignocellulosic biomass beating the biomass in a solvent together with a zeolite based catalyst.

Controllable synthesis of 2- And 3-aryl-benzomorpholines from 2-aminophenols and 4-vinylphenols

We present herein a method for the controllable synthesis of 3-aryl-benzomorpholine and 2-aryl-benzomorpholine cycloadducts via cross-coupling/annulation between electron-rich 2-aminophenols and 4-vinylphenols. Molecular oxygen was successfully used in the reaction as the terminal oxidant and the complete inversion of chemoselectivity was achieved by the adjustment of the solvents and bases at room temperature.

Consolidated production of coniferol and other high-value aromatic alcohols directly from lignocellulosic biomass

Sustainable production of fine chemicals and biofuels from renewable biomass offers a potential alternative to the continued use of finite geological oil reserves. However, in order to compete with current petrochemical refinery processes, alternative biorefinery processes must overcome significant costs and productivity barriers. Herein, we demonstrate the biocatalytic production of the versatile chemical building block, coniferol, for the first time, directly from lignocellulosic biomass. Following the biocatalytic treatment of lignocellulose to release and convert ferulic acid with feruloyl esterase (XynZ), carboxylic acid reductase (CAR) and aldo-keto reductase (AKR), this whole cell catalytic cascade not only achieved equivalent release of ferulic acid from lignocellulose compared to alkaline hydrolysis, but also displayed efficient conversion of ferulic acid to coniferol. This system represents a consolidated biodegradation-biotransformation strategy for the production of high value fine chemicals from waste plant biomass, offering the potential to minimize environmental waste and add value to agro-industrial residues.

Synthesis method of valerolactam alkaloid compound (by machine translation)

The invention discloses a synthesis method, of a valerolactam alkaloid compound. Comprising: 1) reacting thionyl chloride with methanol, then adding ferulic acid, synthesizing ferulic acid methyl ester; 2) reacting 2 -nitrogen hexanone with phosphorus pentachloride; 4) 3, 3 -dibromo -2 - azaltrexone reacts with hydrogen and sodium acetate under the action of potassium iodide to generate 3-bromo 3 -cyclohexanone; 3) reaction, and reacting with hydrogen -2 - and sodium acetate under the action of potassium iodide; and the like 3 -2 . 5) 4) The terpineol prepared in step 3 -) is reacted, with sodium hydroxide, with the terpineol prepared in step -2 2 -) to form a lactam alkaloid compound. The synthetic method has the advantages of accessible raw material sources, mild reaction conditions, and simple reaction process operation. (by machine translation)