22383-86-4

Basic information

• Product Name: 2-HYDROXY-3,4-DIMETHOXY-6-METHYLBENZALDEHYDE
• Synonyms: 2-HYDROXY-3,4-DIMETHOXY-6-METHYLBENZALDEHYDE;3,4-DIMETHOXY-2-HYDROXY-6-METHYLBENZALDEHYDE
• CAS NO: 22383-86-4
• Molecular Formula: C₁₀H₁₂O₄
• Molecular Weight: 196.2
• Product Categories: Aromatic Aldehydes & Derivatives (substituted)
• Mol File: 22383-86-4.mol
• Article Data: 2

Chemical Properties

• Melting Point: 110 °C
• Boiling Point: 314.1°Cat760mmHg
• Flash Point: 121.9°C
• Appearance: /
• Density: 1.197g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.561
• PKA: 7.91±0.20(Predicted)
• CAS DataBase Reference: 2-HYDROXY-3,4-DIMETHOXY-6-METHYLBENZALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-HYDROXY-3,4-DIMETHOXY-6-METHYLBENZALDEHYDE(22383-86-4)
• EPA Substance Registry System: 2-HYDROXY-3,4-DIMETHOXY-6-METHYLBENZALDEHYDE(22383-86-4)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Hazardous Substances Data: 22383-86-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H12O4/c1-6-4-8(13-2)10(14-3)9(12)7(6)5-11/h4-5,12H,1-3H3

Upstream product

• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 6443-69-2 3,4,5-trimethoxytoluene 
• 22383-85-3 2,3,4-trimethoxy-6-methylbenzaldehyde 
• 65195-49-5 2,3,4-trihydroxy-6-methylbenzaldehyde 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 3066-91-9 2,5-dihydroxy-3,4-dimethoxy-6-methyl-benzaldehyde 
• 1026887-24-0 2-{4-[hydroxy-(3,4-dimethoxy-2-hydroxy-6-methyl)phenyl]methylphenyl}-1,3-dioxolane 
• 192809-51-1 tert-Butyl-(2-ethynyl-5,6-dimethoxy-3-methyl-phenoxy)-dimethyl-silane 
• 1025981-70-7 tert-Butyl-[2-(2,2-dibromo-vinyl)-5,6-dimethoxy-3-methyl-phenoxy]-dimethyl-silane 
• 1027994-13-3 5-{(Z)-2-[2-(tert-Butyl-dimethyl-silanyloxy)-3,4-dimethoxy-6-methyl-phenyl]-vinyl}-2-methoxy-phenol 
• 192809-53-3 5-[2-(tert-Butyl-dimethyl-silanyloxy)-3,4-dimethoxy-6-methyl-phenylethynyl]-2-methoxy-phenol 
• 192809-69-1 1-(tert-butyldimethylsiloxy)-2,3-dimethoxy-6-[3-(tert-butyldimethylsiloxy)-4-(methoxyphenyl)ethynyl]-5-methylbenzene 
• 192809-59-9 tert-Butyl-[2-((E)-2-iodo-vinyl)-5,6-dimethoxy-3-methyl-phenoxy]-dimethyl-silane 
• 192809-55-5 (Z)-1-(3,4-dimethoxy-2-hydroxy-5-methylphenyl)-2-(3-hydroxy-4-methoxyphenyl)ethene 
• 192809-61-3 3-(tert-Butyl-dimethyl-silanyloxy)-2-{(E)-2-[3-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-vinyl}-4,5-dimethoxy-1-methyl-benzene 
• 192809-45-3 (Z)-1-(6-acetoxy-5,6-dimethoxy-3-methyl-1-oxocyclohexa-2,4-dien-2-yl)-2-(6-acetoxy-6-methoxy-1-oxocyclohexa-2,4-dien-3-yl)ethene 
• 192809-62-4 (E)-1-(6-acetoxy-5,6-dimethoxy-3-methyl-1-oxocyclohexa-2,4-dien-2-yl)-2-(6-acetoxy-6-methoxy-1-oxocyclohexa-2,4-dien-3-yl)ethene 
• 483-54-5 2,3-dimethoxy-5,6-dimethyl-2,5-cyclohexadiene-1,4-dione  
• 776-33-0 1,4-dihydroxy-2,3-dimethoxy-5,6-dimethylbenzene 

Relevant articles and documents

Fluorogenic Ubiquinone Analogue for Monitoring Chemical and Biological Redox Processes

We report herein the synthesis and characterization of a fluorogenic analogue of ubiquinone designed to reversibly report on redox reactions in biological systems. The analogue, H2B-Q, consists of the redox-active quinone segment found in ubiquinone, 2,3-dimethoxy-1,4-benzoquinone, coupled to a boron-dipyrromethene (BODIPY) fluorophore segment that both imparts lipophilicity in lieu of the isoprenyl tail of ubiquinone, and reports on redox changes at the quinone/quinol segment. Redox sensing is mediated by a photoinduced electron transfer intramolecular switch. In its reduced dihydroquinone form, H2B-QH2 is highly emissive in nonpolar media (quantum yields 55-66%), while once oxidized, the resulting quinone H2B-Q emission is suppressed. Cyclic voltammetry of H2B-Q shows two reversible, 1-electron reduction peaks at -1.05 V and -1.37 V (vs ferrocene) on par with those of ubiquinone. Chemical reduction of H2B-Q by NaBH4 resulted in >200 fold emission enhancement. H2B-QH2 is shown to react with peroxyl radicals, a form of reactive oxygen species (ROS) as well as to cooperatively interact with chromanol (the active segment of α-tocopherol). Kinetic analysis further shows the antioxidant reactivity of the nonfluorescent intermediate semiquinone. We anticipate that the H2B-Q/H2B-QH2 off/on reversible couple may serve as a tool to monitor chemical redox processes in real-time and in a noninvasive manner.