14414-32-5

Basic information

• Product Name: 4-Hydroxy-3,5-dimethoxybenzaldehyde azine
• Synonyms: benzaldehyde,4-hydroxy-3,5-dimethoxy-,[(4-hydroxy-3,5-dimethoxyphenyl)methyle;ne]hydrazone;SYRINGALDAZINE;3,5-DIMETHOXY-4-HYDROXYBENZALAZINE;4-HYDROXY-3,5-DIMETHOXYBENZALDEHYDE AZINE;SYRINGALDAZINE 99%;SYRINGALDAZINE 99+%;syringaldezine
• CAS NO: 14414-32-5
• Molecular Formula: C₁₈H₂₀N₂O₆
• Molecular Weight: 360.36
• EINECS: 238-390-1
• Product Categories: Aromatic Hydrazides, Hydrazines, Hydrazones and Oximes
• Mol File: 14414-32-5.mol
• Article Data: 2

Chemical Properties

• Melting Point: 209-210 °C(lit.)
• Boiling Point: 492.4°C (rough estimate)
• Flash Point: 281.9 °C
• Appearance: green to yellow fine crystalline powder
• Density: 1.3595 (rough estimate)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.5700 (estimate)
• Storage Temp.: 2-8°C
• Solubility: DMF: slightly hazy
• PKA: 8.54±0.40(Predicted)
• CAS DataBase Reference: 4-Hydroxy-3,5-dimethoxybenzaldehyde azine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Hydroxy-3,5-dimethoxybenzaldehyde azine(14414-32-5)
• EPA Substance Registry System: 4-Hydroxy-3,5-dimethoxybenzaldehyde azine(14414-32-5)

Safety Data

• Hazard Codes: Xi,Hazard
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 14414-32-5(Hazardous Substances Data)

Usage

Chemical Properties

green to yellow fine crystalline powder

Uses

Different sources of media describe the Uses of 14414-32-5 differently. You can refer to the following data:
1. Syringaldazine has been used as a substrate to determine the enzymatic activity of the cuticular laccase.
2. Syringaldazine has been used as a substrate to measure the enzymatic activity of recombinant laccase.

Biochem/physiol Actions

Syringaldazine is a dimer of two molecules of 2,6-dimethoxyphenol linked by an azide bridge. It is a phenolic non-autooxidizable laccase-specific compound, that facilitates the detection of fungal laccase in some varieties of fungi. In addition, it also acts as an indicator for peroxidase activity in fungi.

InChI:InChI=1/C18H20N2O6/c1-23-13-5-11(6-14(24-2)17(13)21)9-19-20-10-12-7-15(25-3)18(22)16(8-12)26-4/h5-10,21-22H,1-4H3/b19-9+,20-10+

Upstream product

• 134-96-3 syringic aldehyde 

Downstream Products

• 53669-33-3 4-acetoxy-3,5-dimethoxybenzaldehyde 

Relevant articles and documents

Synthesis of azines in solid state: Reactivity of solid hydrazine with aldehydes and ketones

Highly conjugated azines were prepared by solid state grinding of solid hydrazine and carbonyl compounds such as aldehydes and ketones, using a mortar and a pestle. Complete conversion to the azine product is generally achieved at room temperature within 24 h, without using solvents or additives. The solid-state reactions afford azines as the sole products with greater than 97% yield, producing only water and carbon dioxide as waste.

Syringaldehyde as a scaffold for the synthesis of some biologically potent heterocycles

Syringaldehyde was utilized in synthesis of different heterocyclic systems. Some of the synthesized compounds 2, 7, 8, 10, 11, and 13 were tested for antioxidant activity where they showed ability to inhibit oxidation in kidney and rat brain homogenates using 2, 2′-azinobis (3-ethylbenzothiazoline-6-sulfonic acid) (ABTS). Also, the activity against cancer was examined using the standard MTT method for two human tumor cell lines namely; mammary gland breast cancer MCF-7 and hepatocellular carcinoma HepG2. The highest activity as antioxidant and antitumor agents was exhibited by compounds 8 and 11. However, moderate activities were shown by compounds 10 and 13. While, compounds 2, 7 showed weak activities.