文章目录
Product Overview
Indirubin, with the molecular formula C8H5NO2, is a reddish-orange crystalline compound. It is easily soluble in hot ethanol, slightly soluble in ether, and soluble in hot water, benzene, acetone, and alkali metal hydroxides. Used as a dye and pharmaceutical intermediate, it is involved in the production of the drug Sincophine and the dye Disperse Yellow E-3G. In chemical analysis, it serves as a reagent for determining cuprous ions, thiols, thiophene, and urine blue.
Indirubin Production Process
Chemical synthesis.
Indirubin is prepared by the oxidation of indole or indigo. It was first isolated by French chemist Auguste Laurent. In 1878, Adolf von Baeyer completed the total synthesis of indirubin. By 1880, Baeyer developed a method for synthesizing indirubin from o-nitrocinnamic acid. In 1883, Baeyer patented a method for synthesizing indirubin from o-nitrobenzaldehyde. Since then, synthetic methods for indirubin have gradually replaced extraction from plants as the primary source.
- Start by synthesizing oxime acetyl aniline from aniline trichloroacetaldehyde oxime, then cyclize and hydrolyze to obtain indirubin.
- Dissolve sodium carbonate, sodium nitrite, acetic acid, ice, and water, then pass sulfur dioxide gas until the pH is 1, controlling the temperature to not exceed 10°C. After the reaction, introduce steam to raise the temperature above 30°C. Add the obtained hydroxylamine sulfonic acid sodium to trichloroacetaldehyde and anhydrous sodium carbonate, stir until dissolved, then add aniline, steam, and heat to boiling for 2-3 minutes. Let sit for 1-1.5 hours, cool until crystallization is complete, filter, and dry. The obtained isonitrosoacetyl aniline is added in batches to concentrated sulfuric acid at 50°C, stirred thoroughly, and cooled indirectly with cold water, maintaining the temperature between 60-75°C. After adding all the isonitrosoacetyl aniline, heat to 80°C. After 10-15 minutes, pour the reaction liquid into cold water, let sit until crystallization is complete, filter, wash crystals to neutrality, and dry at 100°C to obtain indirubin. Yield: 105g, 77% (based on actual indigo used), melting point 199-201°C.
- In a 2L reaction flask equipped with a stirrer, thermometer, and dropping funnel, add 130g indigo (0.5mol), 400mL water, and stir to form a uniform suspension. Add 175g sodium chromate (0.5mol) dissolved in 200mL water, then add 6.5g nitrobenzene. Cool to about 5°C in an ice-water bath, then slowly add 285g 63% sulfuric acid, maintaining the reaction temperature between 0-10°C for about 7-8 hours. Let sit overnight, then heat to 65°C and react for 1.5 hours. Cool to room temperature, filter. Discard the water layer (green), add the filter cake to 1300mL water, heat to 50°C, and add sodium hydroxide solution until alkaline. Filter, recover 10g unreacted indigo. After decolorizing the filtrate with activated carbon at 80°C, acidify with hydrochloric acid to pH 3-4, yielding bright orange crystals. Cool and let sit for 24 hours, filter, wash with water to neutrality, and dry at 100°C to obtain indirubin. Yield: 105g, 77% (based on indigo used), melting point 199-201°C.
Applications of Indirubin
- Used as a dye and pharmaceutical intermediate in the production of Sincophine and Disperse Yellow E-3G. It also serves as a reagent for determining cuprous ions, thiols, thiophene, and in dye synthesis.
- Applied as a reagent in thin-layer chromatography or low-color-layer methods for amino acids and amines. It is also used in dye synthesis and chemical analysis.
- Used as a food coloring agent.
Applications of Indirubin
Indirubin is not widely used as a food coloring agent; its primary research and applications are in fuel and pharmaceutical fields.
Packaging and Storage
Storage Conditions: Store in a sealed, light-proof container, away from high temperatures, in a dry, cool, well-ventilated area.
Packaging: Bulk packaging in 25kg cardboard drums; small samples in 1kg foil bags; custom packaging available upon request.
Transportation: Shipped via courier or logistics, with domestic courier delivery within three days and logistics within five days. Prices generally include domestic shipping costs.
Shelf Life: Two years.
