4206-58-0

Basic information

• Product Name: SINAPINALDEHYDE
• Synonyms: 3,5 DIMETHOXY-4-HYDROXYCINNAMALDEHYDE;SINAPALDEHYDE;SINAPALEHYDE;SINAPINALDEHYDE;TRANS-3,5-DIMETHOXY-4-HYDROXYCINNAMALDEHYDE;TRANS-3 5-DIMETHOXY-4-HYDROXY- &;2-Propenal, 3-(4-hydroxy-3,5-dimethoxyphenyl)-, (2E)-;(E)-3-(3,5-Dimethoxy-4-hydroxyphenyl)-2-propene-1-one
• CAS NO: 4206-58-0
• Molecular Formula: C₁₁H₁₂O₄
• Molecular Weight: 208.21
• Product Categories: Aromatic Aldehydes & Derivatives (substituted)
• Mol File: 4206-58-0.mol
• Article Data: 15

Chemical Properties

• Melting Point: 104-106 °C(lit.)
• Boiling Point: 372.3 °C at 760 mmHg
• Flash Point: 146.3 °C
• Appearance: /
• Density: 1.195 g/cm³
• Vapor Pressure: 4.53E-06mmHg at 25°C
• Refractive Index: 1.575
• Storage Temp.: 2-8°C
• PKA: 9.67±0.36(Predicted)
• CAS DataBase Reference: SINAPINALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: SINAPINALDEHYDE(4206-58-0)
• EPA Substance Registry System: SINAPINALDEHYDE(4206-58-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 4206-58-0(Hazardous Substances Data)

Usage

Uses

trans-3,5-Dimethoxy-4-hydroxycinnamaldehyde (Sinapinaldehyde) is suitable for use in the determination of phenolic compounds by HPLC with multiple wavelength detector in grape marc distillates aged in Quercus petraea, Quercus robur and Quercus alba wooden barrels. It is suitable for use in the GC/MS positive ion chemical ionization (PICI) characterization of volatile phenols and benzene aldehydes in various woods.

Definition

ChEBI: A member of the class of cinnamaldehydes that is cinnamaldehyde substituted by a hydroxy group at position 4 and methoxy groups at positions 3 and 5.

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

• 92409-34-2 1-(4-hydroxy-3,5-dimethoxyphenyl)-2-(2'-methoxyphenoxy)-1,3-propanediol 
• 39657-48-2 4-acetoxy-3,5-dimethoxycinnamic acid chloride 
• 71686-40-3 (E)-2,6-dimethoxy-4-(3-oxoprop-1-en-1-yl)phenyl acetate 
• 75-07-0 acetaldehyde 
• 134-96-3 syringic aldehyde 
• 20675-96-1 Syringenin 
• 6627-88-9 4-allyl-2,6-dimethoxyphenol 
• 6318-20-3 O-acetylsyringic acid 
• 90985-68-5 (E)-4-acetoxy-3,5-dimethoxycinnamic acid 
• 530-59-6 trans-3,5-dimethoxy-4-hydroxycinnamic acid 
• 92446-11-2 [(E)-3-(4-Hydroxy-3,5-dimethoxy-phenyl)-acryloyloxymethylene]-dimethyl-ammonium; chloride 
• 249647-14-1 5-hydroxyconiferyl aldehyde 
• 14031-35-7 S-Adenosyl-L-methionine 
• 55211-66-0 3,5-dimethoxy-4-(methoxymethoxy)benzaldehyde 

Downstream Products

• 20736-25-8 3-(4-hydroxy-3,5-dimethoxyphenyl)propan-1-ol 
• 20675-96-1 trans-sinapyl alcohol 
• 71686-40-3 (E)-2,6-dimethoxy-4-(3-oxoprop-1-en-1-yl)phenyl acetate 
• 154461-65-1 sinapyl aldehyde 4-O-β-D-glucopyranoside 
• 134-96-3 syringic aldehyde 
• 80638-49-9 3-(4-hydroxy-3,5-dimethoxyphenyl)propionaldehyde 
• 1290536-73-0 C₃₇H₃₇O₁₅⁽¹⁺⁾ 
• 1159262-04-0 C₂₃H₂₃O₄P 
• 1159262-06-2 C₃₅H₃₄O₄P₂ 
• 100-52-7 benzaldehyde 
• 75-07-0 acetaldehyde 
• 513-85-9 2.3-butanediol 

Relevant articles and documents

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.

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