43073-12-7

Basic information

• Product Name: 4,5-dimethoxybenzene-1,2-dicarbaldehyde
• CAS NO: 43073-12-7
• Molecular Formula: C₁₀H₁₀O₄
• Molecular Weight: 194.184
• Mol File: 43073-12-7.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 371.4°C at 760 mmHg
• Flash Point: 168.2°C
• Density: 1.207g/cm³
• Vapor Pressure: 1.04E-05mmHg at 25°C
• Refractive Index: 1.574
• CAS DataBase Reference: 4,5-dimethoxybenzene-1,2-dicarbaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 4,5-dimethoxybenzene-1,2-dicarbaldehyde(43073-12-7)
• EPA Substance Registry System: 4,5-dimethoxybenzene-1,2-dicarbaldehyde(43073-12-7)

Safety Data

• Hazardous Substances Data: 43073-12-7(Hazardous Substances Data)

Usage

Description

4,5-dimethoxybenzene-1,2-dicarbaldehyde, commonly known as syringaldehyde, is a chemical compound characterized by a benzene ring with two aldehyde functional groups and two methoxy substituents. It is predominantly sourced from plant lignin and is recognized for its aromatic properties and reactivity, which make it a versatile compound for various industrial applications.

Uses

Used in Flavor and Fragrance Industry:
4,5-dimethoxybenzene-1,2-dicarbaldehyde is used as a precursor in the synthesis of vanillin, a widely used flavoring agent known for its characteristic vanilla scent and taste. Its role in this industry is crucial for producing natural vanilla flavor in food products and fragrances.
Used in Pharmaceutical Industry:
Syringaldehyde is utilized as a starting material for the synthesis of various pharmaceutical compounds due to its reactive aldehyde groups. Its potential antioxidant and antimicrobial properties are also being explored for development into new drugs or supplements.
Used in Cosmetic Industry:
In the cosmetic sector, 4,5-dimethoxybenzene-1,2-dicarbaldehyde is employed for its aromatic characteristics, contributing to the scent profiles of various products. Additionally, its potential antimicrobial properties could be harnessed for the development of preservative-free formulations.
Used in Environmental Applications:
Syringaldehyde plays a role in the degradation of lignin, a complex organic polymer found in plant cell walls. Its involvement in this natural process is significant for the breakdown and recycling of plant materials in the environment, contributing to the sustainable management of biomass.
Used in Chemical Research:
Due to its unique structure and reactivity, 4,5-dimethoxybenzene-1,2-dicarbaldehyde serves as a valuable compound in chemical research, particularly in the study of organic reactions, synthesis methodologies, and the development of new materials with specific properties.

Upstream product

• 22943-99-3 (4,5-dimethoxy-1,2-phenylene)dimethanol 
• 1134-52-7 1,2-Dimethoxy-4,5-bis(chloromethyl)benzene 
• 75833-56-6 1,2-bisdichloromethyl-4,5-dimethoxybenzene 
• 50-00-0 formaldehyd 
• 93-07-2 Veratric acid 
• 132233-78-4 4,5-dimethoxy-2-(dimethoxymethyl)benzaldehyde 
• 531-88-4 5,6-dimethoxyphthalide 
• 91-16-7 1,2-dimethoxybenzene 
• 577-68-4 m-hemipinic acid 
• 103477-58-3 2-(2-bromo-4,5-dimethoxyphenyl)-1,3-dioxolane 
• 132628-76-3 2-(1,3-dioxolan-2-yl)-4,5-dimethoxybenzaldehyde 
• 54370-00-2 2-bromo-4,5-dimethoxybenzyl alcohol 
• 5392-10-9 2-bromo-4,5-dimethoxybenzaldehyde 
• 6286-46-0 2-bromo-4,5-dimethoxybenzoic acid 

Downstream Products

• 121254-74-8 3-(tert-Butyl-dimethyl-silanyl)-6,7-dimethoxy-2-phenyl-naphthalen-1-ol 
• 75833-50-0 4,5-dihydroxyphthalaldehyde 
• 13705-95-8 6,7-dimethoxyphthalazine 
• 43073-13-8 1,2-bis(dibromomethyl)4,5-dimethoxybenzene 
• 170160-98-2 1,2-diethynyl-4,5-dimethoxybenzene 
• 143739-62-2 iodure de 6,7-dimethoxy-3-ethoxycarbonyl-N-methylisoquinolinium 
• 1268396-41-3 C₁₈H₂₂O₁₀ 
• 1401250-26-7 C₂₄H₂₈N₂O₃ 

Relevant articles and documents

Enantioselective Iridium-Catalyzed Phthalide Formation through Internal Redox Allylation of Phthalaldehydes

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Traceless and Chemoselective Amine Bioconjugation via Phthalimidine Formation in Native Protein Modification

ortho-Phthalaldehyde (OPA) and its derivatives are found to react chemoselectively with amino groups on peptides and proteins rapidly and tracelessly under the physiological condition via formation of phthalimidines, which provides a novel and promising approach when performing bioconjugation on native proteins. The notable advantages of this method over the existing native protein lysine-labeling approaches include a traceless process, a self-reacting, specific and fast reaction, ease of operation, and the ability to use nonhydrolyzable reagents. Its applications have been effectively demonstrated including conjugation of peptides and proteins, and generation of an active PEGlyated l-asparaginase.

Water-soluble isoindolo[2,1-a]quinoxalin-6-imines: In vitro antiproliferative activity and molecular mechanism(s) of action

Water-soluble isoindoloquinoxalin (IIQ) imines and the corresponding acetates were conveniently prepared from the key intermediates 2-(2′-aminophenyl)-2H-isoindole-1-carbonitriles obtained by a Strecker reaction between substituted 1,2-dicarbaldehydes and 1,2-phenylenediamines. Both series were screened by the National Cancer Institute (Bethesda, MD) and showed potent antiproliferative activity against a panel of 60 human tumor cell lines. Several of the novel compounds showed GI50 values at a nanomolar level on the majority of the tested cell lines. Among IIQ derivatives, methoxy substituents at positions 3 and 8 or/and 9 were especially effective in impairing cell cycle progression and inducing apoptosis in cancer cells. These effects were associated to IIQ-mediated impairment of tubulin polymerization at pharmacologically significant concentrations of tested compounds. In addition, impaired DNA topoisomerase I functions and perturbation in telomere architecture were observed in cells exposed to micromolar concentrations of IIQ derivatives. The above results suggest that IIQ derivatives exhibit multi-target cytotoxic activities.