458-35-5

Basic information

• Product Name: CONIFERYL ALCOHOL
• Synonyms: 3-(4-Hydroxy-3-methoxyphenyl)-2-propen-1-ol, 4-Hydroxy-3-methoxycinnamyl alcohol;1-(3-Methoxy-4-hydroxyphenyl)propene-3-ol;3-(3-Methoxy-4-hydroxyphenyl)-2-propene-1-ol;3-(4-Hydroxy-3-methoxyphenyl)-2-propene-1-ol;4-(3-Hydroxy-1-propenyl)-2-methoxyphenol;p-Coniferyl alcohol;Coniferyl alcohol,99%;4-((E)-3-Hydroxyprop-1-enyl)-2-methoxyphenol
• CAS NO: 458-35-5
• Molecular Formula: C₁₀H₁₂O₃
• Molecular Weight: 180.2
• EINECS: 207-277-9
• Product Categories: Benzhydrols, Benzyl & Special Alcohols
• Mol File: 458-35-5.mol
• Article Data: 84

Chemical Properties

• Melting Point: 75-80 °C(lit.)
• Boiling Point: 163-165 °C3 mm Hg(lit.)
• Flash Point: 163-165°C/3mm
• Appearance: /
• Density: 1.1272 (rough estimate)
• Vapor Pressure: 6.93E-07mmHg at 25°C
• Refractive Index: 1.5080 (estimate)
• Storage Temp.: −20°C
• Solubility: alcohol: moderately soluble(lit.)
• PKA: 9.99±0.35(Predicted)
• Sensitive: Light Sensitive
• Stability: Light Sensitive
• Merck: 14,2504
• BRN: 2048961
• CAS DataBase Reference: CONIFERYL ALCOHOL(CAS DataBase Reference)
• NIST Chemistry Reference: CONIFERYL ALCOHOL(458-35-5)
• EPA Substance Registry System: CONIFERYL ALCOHOL(458-35-5)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• RTECS: SL5367000
• F: 4.8-8-10-23
• TSCA: Yes
• Hazardous Substances Data: 458-35-5(Hazardous Substances Data)

Usage

Description

Coniferyl alcohol, a phenylpropanoid and one of the main monolignols, is a key compound in the biosynthesis of lignin, an essential component of plant cell walls. It is derived from the reduction of the carboxy functional group in cinnamic acid and the addition of a hydroxy and a methoxy substituent to the aromatic ring. Coniferyl alcohol is a beige crystalline powder and is one of the preferred substrates of the Eucalyptus globus enzyme.

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 
• 331-39-5 caffeic acid 
• 2196-18-1 3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone 
• 3063-86-3 3-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-1-propanol 
• 1135-24-6 (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid 

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 
• 74741-32-5 6-allyl-3-(4-hydroxy-3-methoxyphenyl)-2-hydroxymethyl-1,4-benzodioxan 
• 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 

Relevant articles and documents

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.

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.

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.