4206-58-0

Usage

Uses

Used in Analytical Chemistry:
SINAPINALDEHYDE is used as a marker compound for the determination of phenolic compounds in grape marc distillates aged in Quercus petraea, Quercus robur, and Quercus alba wooden barrels. It is employed in High-Performance Liquid Chromatography (HPLC) with a multiple wavelength detector, allowing for accurate identification and quantification of phenolic compounds in these distillates.
Used in Gas Chromatography/Mass Spectrometry (GC/MS) Analysis:
SINAPINALDEHYDE is utilized as a reference compound for the GC/MS positive ion chemical ionization (PICI) characterization of volatile phenols and benzene aldehydes in various types of wood. This application aids in the identification and analysis of these volatile compounds, which are essential for understanding the chemical composition and properties of different wood species.

InChI:InChI=1/C11H12O4/c1-14-9-6-8(4-3-5-12)7-10(15-2)11(9)13/h3-7,13H,1-2H3/b4-3+

Upstream product

• 20675-96-1 Syringenin 
• 92446-11-2 [(E)-3-(4-Hydroxy-3,5-dimethoxy-phenyl)-acryloyloxymethylene]-dimethyl-ammonium; chloride 
• 6318-20-3 O-acetylsyringic acid 
• 134-96-3 syringic aldehyde 
• 42041-51-0 methyl (E)-sinapate 
• 20675-96-1 trans-sinapyl alcohol 
• 75-07-0 acetaldehyde 
• 6627-88-9 4-allyl-2,6-dimethoxyphenol 
• 39657-47-1 O-acetylsyringic acid chloride 
• 530-59-6 trans-3,5-dimethoxy-4-hydroxycinnamic acid 
• 53669-33-3 4-acetoxy-3,5-dimethoxybenzaldehyde 
• 71686-40-3 (E)-2,6-dimethoxy-4-(3-oxoprop-1-en-1-yl)phenyl acetate 
• 39657-48-2 4-acetoxy-3,5-dimethoxycinnamic acid chloride 
• 92409-34-2 1-(4-hydroxy-3,5-dimethoxyphenyl)-2-(2'-methoxyphenoxy)-1,3-propanediol 

Downstream Products

• 1290536-73-0 C₃₇H₃₇O₁₅⁽¹⁺⁾ 
• 1159262-04-0 C₂₃H₂₃O₄P 
• 1159262-06-2 C₃₅H₃₄O₄P₂ 
• 100-52-7 benzaldehyde 
• 958644-05-8 C₂₀H₃₃O₇P 
• 80638-49-9 3-(4-hydroxy-3,5-dimethoxyphenyl)propionaldehyde 
• 20675-96-1 Syringenin 

Relevant academic research and scientific papers

Total Syntheses and Anti-inflammatory Activities of Syringin and Its Natural Analogues

Syringin (1), a natural bioactive glucoside isolated from the root of Acanthopanax senticosus (Rupr. Maxim.) Harms, possesses significant anti-inflammatory activity. In this study, we have accomplished the total syntheses of syringin (1), along with its natural analogues 2-12, from a common starting material, syringaldehyde (13), in 4-8 steps with an overall yields of 11.8-61.3%. The anti-inflammatory activities of these compounds were determined against NO production in the LPS-stimulated RAW264.7 cells. Among them, compounds 1-5, 7, and 9 exhibited different levels of anti-inflammatory activity.

PIGMENTED AND FLUORESCENT COMPOUNDS DERIVED FROM THE ADDITION OF A PRIMARY OR SECONDARY AMINE TO AN ALDEHYDE

The invention provides a compound of formula (I): wherein R1, R2, and R3 have any of the values described in the specification, as well as compositions comprising a compound of formula (I), methods for preparing compounds of formula (I), and methods for detecting the presence of an amine in a sample. The compounds are useful as pigments.

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.

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.

4-Chloro-2,6-Pyridinedicarboxylic Acid Functionalized Mesoporous Silica Nanocomposites for the Synthesis of Sinapaldehyde

Abstract: 4-Chloro-2,6-pyridinedicarboxylic acid (CPDA) functionalized mesoporous silica SBA-15 nanocomposites (SBA/5CPDA) were synthesized and characterized for the Knoevenagel condensation of syringaldehyde and acetaldehyde to synthesize sinapaldehyde i

Biomimetic Oxidation of Monolignol Acetate and p-Coumarate by Silver Oxide in 1,4-Dioxane

Lignin acylated with acetate and/or p-coumarate is common in many herbaceous plants. Herein, the biomimetic oxidation of ?3-acylated monolignols with Ag2O was studied to understand the effect of ?3-acyl groups on monolignol polymerization. The oxidation of sinapyl acetate gave ?3-acylated and α-acylated β-O-4 dimers in 71 and 9.5% yields, respectively. The oxidation of sinapyl p-coumarate produced ?3-acylated β-O-4 and ?3-acylated tetralin β-β dimers in 53 and 16% yields, respectively. Only the sinapyl alcohol moiety in sinapyl p-coumarate reacted, and the p-coumarate moiety remained unchanged, suggesting that p-coumaric acid is not incorporated into the lignin backbone in the acylated lignins. All of the ?3-acylated monolignols used in this study produced the ?3-acylated β-O-4 dimers, which suggests that the ?3-acylated monolignols act as lignin monomers. The relatively high yields of the β-O-4 dimers indicate that Ag2O oxidation of the monolignols can be used as an easy method for synthesizing the β-O-4 dimer model compounds.

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.

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.

Selective oxidation of lignin model compounds

Lignin, the planet’s most abundant renewable source of aromatic compounds, is difficult to degrade efficiently to well-defined aromatics. We developed a microwave-assisted catalytic Swern oxidation system using an easily prepared catalyst, MoO2Cl2(DMSO)2, and DMSO as the solvent and oxidant. It demonstrated high efficiency in transforming lignin model compounds containing the units and functional groups found in native lignins. The aromatic ring substituents strongly influenced the selectivity of β-ether phenolic dimer cleavage to generate sinapaldehyde and coniferaldehyde, monomers not usually produced by oxidative methods. Time-course studies on two key intermediates provided insight into the reaction pathway. Owing to the broad scope of this oxidation system and the insight gleaned with regard to its mechanism, this strategy could be adapted and applied in a general sense to the production of useful aromatic chemicals from phenolics and lignin.

Microwave-Assisted Synthesis of Phenylpropanoids and Coumarins: Total Synthesis of Osthol

Herein we describe a one-pot microwave-assisted method for the synthesis of cinnamic acid and coumarin derivatives. The synthesis begins with an aldehyde synthon, and the chosen reaction conditions determine whether a cinnamic acid or coumarin derivative is formed. A regioselective Claisen rearrangement was also efficiently incorporated into the synthetic sequence to further increase the complexity of the product. Notably, this approach provides high product yields and selectivities without the need of a phenol protecting group.