458-36-6

Basic information

• Product Name: 4-HYDROXY-3-METHOXYCINNAMALDEHYDE
• Synonyms: CONIFERALDEHYDE;CONIFERYL ALDEHYDE;4-HYDROXY-3-METHOXYCINNAMALDEHYDE;4'-hydroxy-3'-methoxyciаnaldehyde;2-Propenal, 3-(4-hydroxy-3-methoxyphenyl)-;4-HYDROXY-3-METHOXYCINNAMALDEHDYE;2-Methoxy-4-(3-oxo-1-propenyl)phenol;2-Methoxy-4-(3-oxopropene-1-yl)phenol
• CAS NO: 458-36-6
• Molecular Formula: C₁₀H₁₀O₃
• Molecular Weight: 178.18
• EINECS: 207-278-4
• Product Categories: Aromatic Aldehydes & Derivatives (substituted)
• Mol File: 458-36-6.mol
• Article Data: 35

Chemical Properties

• Melting Point: 80-82 °C(lit.)
• Boiling Point: 175 °C5 mm Hg(lit.)
• Flash Point: 136.8 °C
• Appearance: /
• Density: 1.1562 g/cm3 (101.5 ºC)
• Vapor Pressure: 4.88E-05mmHg at 25°C
• Refractive Index: 1.65635
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 9.65±0.31(Predicted)
• Stability: Air Sensitive
• CAS DataBase Reference: 4-HYDROXY-3-METHOXYCINNAMALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-HYDROXY-3-METHOXYCINNAMALDEHYDE(458-36-6)
• EPA Substance Registry System: 4-HYDROXY-3-METHOXYCINNAMALDEHYDE(458-36-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 458-36-6(Hazardous Substances Data)

Usage

Description

4-Hydroxy-3-methoxycinnamaldehyde, an isoflavonoid, is a naturally occurring compound that has been isolated from various plant sources such as the heartwood of Gliricidia sepium, seed kernels of Melia azedarach L, and barks of Cinnamomum cebuense. It is a member of the cinnamaldehydes class, characterized by the presence of a hydroxy group at position 4 and a methoxy group at position 3.

Uses

Used in Antioxidant and Antiradical Studies:
4-Hydroxy-3-methoxycinnamaldehyde is used as a subject in studies investigating the antioxidant and antiradical activities of ferulates. It is particularly useful in a β-carotene-linoleate model system and a DPPH radical scavenging assay, which are employed to evaluate the compound's potential as a natural antioxidant and its ability to neutralize free radicals.
Used in Pharmaceutical Industry:
As an isoflavonoid with potential biological activities, 4-Hydroxy-3-methoxycinnamaldehyde can be used as a starting material or a key intermediate in the development of new pharmaceutical compounds. Its antioxidant and antiradical properties make it a promising candidate for applications in the development of drugs targeting various diseases, including those related to oxidative stress and inflammation.
Used in Cosmetics Industry:
Due to its antioxidant properties, 4-Hydroxy-3-methoxycinnamaldehyde can be utilized in the cosmetics industry as an active ingredient in skincare and beauty products. It may help protect the skin from environmental stressors, such as free radicals and oxidative damage, thereby promoting skin health and delaying the signs of aging.
Used in Agricultural Industry:
The insecticidal activity of the hot dichloromethane extract of heartwood of Gliricidia sepium, which contains 4-Hydroxy-3-methoxycinnamaldehyde, suggests that this compound could be used as a natural insecticide or a component in the development of biopesticides for the agricultural industry. This could provide an environmentally friendly alternative to synthetic chemical pesticides.

InChI:InChI=1/C10H10O3/c1-13-10-7-8(3-2-6-11)4-5-9(10)12/h2-7,12H,1H3/b3-2-

Upstream product

• 458-35-5 coniferol 
• 458-35-5 coniferal alcohol 
• 480-18-2 taxifolin 
• 97-53-0 4-allylguaiacol 
• 65401-83-4 (E)-2-methoxy-4-(3-oxoprop-1-en-1-yl)phenyl acetate 
• 131946-61-7 4-[1-Hydroxy-2-(4,4,6-trimethyl-5,6-dihydro-4H-[1,3]oxazin-2-yl)-ethyl]-2-methoxy-phenol 
• 92446-10-1 [(E)-3-(4-Hydroxy-3-methoxy-phenyl)-acryloyloxymethylene]-dimethyl-ammonium; chloride 
• 1135-24-6 (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 5533-00-6 3-methoxy-4-methoxymethoxy-benzaldehyde 
• 121-33-5 vanillin 
• 1485529-16-5 (E)-ethyl 3-(4-((tert-butyldimethylsilyl)oxy)-3-methoxyphenyl)acrylate 
• 290820-48-3 (E)-3-( 4-( (tert-butyldimethylsilyl)oxy)-3-methoxyphenyl)prop-2-en-1-ol 
• 290820-47-2 (2E)-3-[4-[[tert-butyldimethylsilyl]oxy]-3-methoxyphenyl]acrylaldehyde 
• 7382-59-4 guaiacylglycerol-β-guaiacyl ether 

Downstream Products

• 121-33-5 vanillin 
• 65401-77-6 1-hydroxy-3-(4-hydroxy-3-methoxy-phenyl)-propane-1,3-disulfonic acid 
• 65401-83-4 (E)-2-methoxy-4-(3-oxoprop-1-en-1-yl)phenyl acetate 
• 127057-19-6 (2E)-3-(4-ethoxy-3-methoxyphenyl)acrylaldehyde 
• 2305-13-7 3-Guaiacylpropanol 
• 458-35-5 coniferal alcohol 
• 130878-30-7 (E)-3-(3-Methoxy-4-trimethylsilanyloxy-phenyl)-propenal 
• 824-46-4 methoxyhydroquinone 
• 121-34-6 3-methoxy-4-hydroxybenzoic acid 
• 306-08-1 Homovanillic acid 
• 458-35-5 coniferol 
• 132748-08-4 coniferyl aldehyde 4-O-β-D-glucopyranoside 
• 626201-07-8 (R)-3-(3,4-Dihydroxy-phenyl)-2-[(E)-3-(4-hydroxy-3-methoxy-phenyl)-allylamino]-propionic acid methyl ester 
• 58045-88-8 3,4-dimethoxycinnamaldehyde 

Relevant articles and documents

In vivo Structure-Activity Relationship of Dihydromethysticin in Reducing Nicotine-Derived Nitrosamine Ketone (NNK)-Induced Lung DNA Damage against Lung Carcinogenesis in A/J Mice

Lung cancer is the leading cause of cancer-related deaths and chemoprevention should be developed. We recently identified dihydromethysticin (DHM) as a promising candidate to prevent NNK-induced lung tumorigenesis. To probe its mechanisms and facilitate its future translation, we investigated the structure-activity relationship of DHM on NNK-induced DNA damage in A/J mice. Twenty DHM analogs were designed and synthesized. Their activity in reducing NNK-induced DNA damage in the target lung tissues was evaluated. The unnatural enantiomer of DHM was identified to be more potent than the natural enantiomer. The methylenedioxy functional moiety did not tolerate modifications while the other functional groups (the lactone ring and the ethyl linker) accommodated various modifications. Importantly, analogs of high structural similarity to DHM with distinct efficacy in reducing NNK-induced DNA damage have been identified. They will serve as chemical probes to elucidate the mechanisms of DHM in blocking NNK-induced lung carcinogenesis.

Synthesis and evaluation of antioxidant properties of 2-substituted quinazolin-4(3H)-ones

Quinazolinones represent an important scaffold in medicinal chemistry with diverse biological activities. Here, two series of 2-substituted quinazolin-4(3H)-ones were synthesized and evaluated for their antioxidant properties using three different methods, namely DPPH, ABTS and TEACCUPRAC, to obtain key information about the structure-antioxidant activity relationships of a diverse set of substituents at position 2 of the main quinazolinone scaffold. Regarding the antioxidant activity, ABTS and TEACCUPRAC assays were more sensitive and gave more reliable results than the DPPH assay. To obtain antioxidant activity of 2-phenylquinazolin-4(3H)-one, the presence of at least one hydroxyl group in addition to the methoxy substituent or the second hydroxyl on the phenyl ring in the ortho or para positions is required. An additional ethylene linker between quinazolinone ring and phenolic substituent, present in the second series (compounds 25a and 25b), leads to increased antioxidant activity. Furthermore, in addition to antioxidant activity, the derivatives with two hydroxyl groups in the ortho position on the phenyl ring exhibited metal-chelating properties. Our study represents a successful use of three different antioxidant activity evaluation methods to define 2-(2, 3-dihydroxyphenyl)quinazolin-4(3H)-one 21e as a potent antioxidant with promising metal-chelating properties.

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.