458-36-6

Usage

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 4-HYDROXY-3-METHOXYCINNAMALDEHYDE 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

• 62427-71-8 (E)-3-[3-methoxy-4-(methoxymethoxy)phenyl]acrylaldehyde 
• 458-35-5 coniferal alcohol 
• 480-18-2 taxifolin 
• 1135-24-6 3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 65401-83-4 (E)-2-methoxy-4-(3-oxoprop-1-en-1-yl)phenyl acetate 
• 97-53-0 4-allylguaiacol 
• 2785-87-7 2-methoxy-4-n-propylphenol 
• 7382-59-4 guaiacylglycerol-β-guaiacyl ether 
• 3054-95-3 acrylaldehyde diethyl acetal 
• 203861-62-5 2-methoxy-4-iodophenol 
• 1430215-03-4 (2E)-3-(4-hydroxy-3-methoxyphenyl)-N-methoxy-N-methylacrylamide 
• 93-28-7 eugenol acetate 
• 4125-45-5 4-allyl-(1-allyloxy)-2-methoxybenzene 
• 2309-07-1 Methyl ferulate 

Downstream Products

• 121-33-5 vanillin 
• 626201-07-8 (R)-3-(3,4-Dihydroxy-phenyl)-2-[(E)-3-(4-hydroxy-3-methoxy-phenyl)-allylamino]-propionic acid methyl ester 
• 1346752-20-2 methyl (R)-3-(4-hydroxy-3-methoxyphenyl)-3-hydroxypropanoate 
• 121-34-6 3-methoxy-4-hydroxybenzoic acid 
• 1135-24-6 3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 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 
• 132748-08-4 coniferyl aldehyde 4-O-β-D-glucopyranoside 
• 24058-19-3 2,3-bis-(4-hydroxy-3-methoxybenzylidene)succinaldehyde 
• 24058-21-7 2-[2-hydroxy-3-methoxy-5-(3-oxopropenyl)phenyl]-3-[4-hydroxy-3-methoxyphenyl]propenal 
• 123022-35-5 (2E,4E)-5-[4-hydroxy-3-methoxyphenyl]penta-2,4-dienoic acid 

Relevant academic research and scientific papers

Discovery of novel diphenylbutene derivative ferroptosis inhibitors as neuroprotective agents

Ferroptosis is a regulated and iron-dependent cell death. Ferroptosis inhibitors are promising for treating many neurological diseases. Herein, with phenotypic assays, we discovered a new diphenylbutene derivative ferroptosis inhibitor, DPT. Based on this hit, we synthesized fourteen new diphenylbutene derivatives, evaluated their ferroptosis inhibitory activities in HT22 mouse hippocampal neuronal cells, and found that three compounds exhibited improved inhibitory activities compared with DPT. Among these active compounds, compound 3f displayed the most potent anti-ferroptosis activity (EC50 = 1.7 μM). Further studies demonstrated that 3f is a specific ferroptosis inhibitor. And we revealed that different from the classic ferroptosis inhibitors, 3f blocked ferroptosis by increasing FSP1 protein level. Moreover, 3f can penetrate blood-brain barrier (BBB). In a rat model of ischemic stroke, 3f effectively mitigated cerebral ischemic injury. Therefore, we are confirmed that 3f, as a novel ferroptosis inhibitor with a new scaffold, is promising for further development as an agent against neurological diseases.

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.

Method for preparing olefine aldehyde by catalyzing terminal alkyne or terminal conjugated eneyne and diphosphine ligand used in method

The invention discloses a method for preparing olefine aldehyde by catalyzing terminal alkyne or terminal conjugated eneyne and a diphosphine ligand used in the method. According to the invention, indole-substituted phosphoramidite diphosphine ligand which is stable in air and insensitive to light is synthesized by utilizing a continuous one-pot method, and the indole-substituted phosphoramidite diphosphine ligand and a rhodium catalyst are used for jointly catalyzing to successfully achieve a hydroformylation reaction of aromatic terminal alkyne and terminal conjugated eneyne under the condition of synthesis gas for the first time, so that an olefine aldehyde structure compound can be rapidly and massively prepared, and particularly, a polyolefine aldehyde structure compound which is more difficult to synthesize in the prior art can be easily prepared and synthesized, and a novel method is provided for synthesis and modification of drug molecules, intermediates and chemical products.

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.

Biocatalytic reduction of α,β-unsaturated carboxylic acids to allylic alcohols

We have developed robust in vivo and in vitro biocatalytic systems that enable reduction of α,β-unsaturated carboxylic acids to allylic alcohols and their saturated analogues. These compounds are prevalent scaffolds in many industrial chemicals and pharmaceuticals. A substrate profiling study of a carboxylic acid reductase (CAR) investigating unexplored substrate space, such as benzo-fused (hetero)aromatic carboxylic acids and α,β-unsaturated carboxylic acids, revealed broad substrate tolerance and provided information on the reactivity patterns of these substrates. E. coli cells expressing a heterologous CAR were employed as a multi-step hydrogenation catalyst to convert a variety of α,β-unsaturated carboxylic acids to the corresponding saturated primary alcohols, affording up to >99percent conversion. This was supported by the broad substrate scope of E. coli endogenous alcohol dehydrogenase (ADH), as well as the unexpected CC bond reducing activity of E. coli cells. In addition, a broad range of benzofused (hetero)aromatic carboxylic acids were converted to the corresponding primary alcohols by the recombinant E. coli cells. An alternative one-pot in vitro two-enzyme system, consisting of CAR and glucose dehydrogenase (GDH), demonstrates promiscuous carbonyl reductase activity of GDH towards a wide range of unsaturated aldehydes. Hence, coupling CAR with a GDH-driven NADP(H) recycling system provides access to a variety of (hetero)aromatic primary alcohols and allylic alcohols from the parent carboxylates, in up to >99percent conversion. To demonstrate the applicability of these systems in preparative synthesis, we performed 100 mg scale biotransformations for the preparation of indole-3-aldehyde and 3-(naphthalen-1-yl)propan-1-ol using the whole-cell system, and cinnamyl alcohol using the in vitro system, affording up to 85percent isolated yield.

METHOD OF SELECTIVELY OXIDIZING LIGNIN

A method of selectively reacting lignin or a lignin-derived reactant to yield an aromatic product. The method includes the step of reacting lignin or a lignin-derived reactant with a molybdenum-containing catalyst, in a solvent, and optionally in the presence of an oxidant, for a time and a temperature wherein at least a portion of the lignin or lignin-derived reactant is selectively converted into an aromatic product, preferably coniferaldehyde and/or sinapaldehyde.

Biotransformation of eugenol to vanillin by a novel strain Bacillus safensis SMS1003

Due to the extensive applications of vanillin as flavored compound and increasing consumers concern for its natural and environment friendly mode of production, present work was focused on the selection of bacterial isolate capable of producing vanillin using eugenol biotransformation. Bacterial strain SMS1003 is evidenced as the potential strain for vanillin production and identified as Bacillus safensis (GeneBank accession no. MG561863) using biochemical tests and molecular phylogenic analysis of its 16S rDNA gene sequence. Molar yield of vanillin reached up to 10.7% (0.055 g/L) at 96 h of biotransformation using growing culture of B. safensis SMS1003 in following culture conditions: eugenol concentration 500 mg/L; temperature 37 °C; initial pH 7.0; inoculum volume 4%; volume of culture media 10%; and shaking speed 180 rpm. Vanillin was detected as the single metabolite with a molar yield of 26% (0.12 g/L) at 96 h using resting cells of B. safensis SMS1003. Product confirmation was based on spectral scan using photodiode array detector, Fourier-transform infrared spectroscopy, high-performance liquid chromatography, and mass spectroscopy.

DDQ-mediated oxidation of allylarenes: Expedient access to cinnamaldehyde-containing phenylpropanoids

Phenylpropanoid natural products containing a cinnamaldehyde motif were easily synthesized from allylarenes mediated by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) oxidation. Representative examples described herein are five types of 4-hydroxycinnamaldehyde derivatives from monolignols biosynthesis, Boropinal C, and 7-methoxywutaifuranal from plant extracts. Especially, simple synthesis of 7-methoxywutaifuranal was exploited through selective mono-oxidation and subsequent isomerization-ring-closing-metathesis strategy.

Synthesis method of 4-hydroxycinnamaldehyde compound

The invention relates to the field of organic synthesis and agricultural chemistry, and particularly discloses a synthesis method of a 4-hydroxycinnamaldehyde compound shown as a formula II. The synthesis method comprises the following steps: with 4-hydroxy-allylbenzene as a raw material, firstly performing hydroxyl protection, then with 2, 3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) as an oxidant and water (H2O) as a nucleophile, oxidizing an allyl group into alpha, beta-unsaturated aldehyde (namely, a cinnamaldehyde structure) under a relatively mild condition, and finally performing deprotection to obtain a target product. The invention elaborates a novel synthesis method of the 4-hydroxycinnamaldehyde compound. The novel synthesis method has the characteristics of no transition metalparticipation, a simple and mild reaction condition, high product yield and the like, and has a wide application prospect in the field of the agricultural chemistry, especially in plant science and bioenergy conversion.