Indole-3-Carbinol (I3C) is a naturally occurring compound in cruciferous plants. Indole 3 carbinol powder has received much attention in recent years for its potential anticancer and immunomodulatory effects. For industrial applications and research needs, pure Indole 3 carbinol is usually prepared by chemical synthesis in laboratories and plants. The synthesis of Indole 3 carbinol powder is described in detail below. This includes its raw materials, reaction principles, synthetic routes, and purification processes.
What Is Indole 3 carbinol powder?
Indole 3 carbinol is an indole derivative. Its chemical structure is a methanol group attached to the indole ring. The chemical formula is C9H9NO and the molecular weight is 147.17 g/mol. Indole 3 carbinol powder has a simple structure. This has high chemical stability and biological activity. Its chemical reactivity is mainly related to the indole ring and the methanol group.
Indole 3 carbinol bulk powder is a white or off-white crystalline powder. It is readily soluble in organic solvents such as ethanol and ethyl acetate and slightly soluble in water. Its synthetic process involves the chemical modification of indole and its derivatives. The reaction conditions are relatively mild. However, the requirement for purity is high.
Overview of Synthetic Methods
The synthetic methods of Indole 3 carbinol powder are mainly divided into two kinds:
● Synthesis method using indole as starting material:
Indole-3-methanol is obtained by reacting indole with formaldehyde, which is suitable for laboratory and small-scale synthesis.
●Extraction from plants and chemical modification method:
Indoles are first extracted from cruciferous plants. Such as indole-3-acetonitrile (precursor of I3C). Then Indole 3 carbinol powder is synthesised by chemical reaction. This method is suitable for large-scale production.
Synthesis Methods
The detailed process of these two synthetic methods are described below.
1. Chemical synthesis method using indole as starting material
This method is mainly suitable for small-scale preparation in the laboratory, and its reaction steps include the methylation of indole and the subsequent redox process. The following are the detailed steps:
①Raw material preparation
●Indole: As the main raw material of the reaction, indole is an aromatic compound extracted from coal tar or obtained by artificial synthesis.
●Formaldehyde: used as a methylation reagent, often in the form of a 37% aqueous solution (formalin).
●Ethanol and water: used as solvents to condition the reaction medium.
② Synthesis Reaction Procedure
●Step 1: Methylation of indole
Add a certain amount of aqueous solution of indole and formaldehyde (formalin) to the reaction vessel and add appropriate amount of ethanol as solvent. Adjust the reaction temperature to 60°C to 70°C and carry out the reaction under stirring conditions.
The chemical equation of the reaction is given below:
\{\text{Indole} + \text{Formaldehyde} \rightarrow \text{Indole-3-methanol} \]
In the reaction, formaldehyde and indole under acidic or basic conditions undergo a nucleophilic addition reaction, in which the carbon in formaldehyde binds to the 3-position of the indole ring to form indole-trimethanol. This process requires pH control in the neutral or slightly acidic range to ensure reaction rate and yield.
●Step 2: Extraction and purification of the product
After completion of the reaction, it was cooled to room temperature, and excess water was added to the reaction mixture to precipitate out the product. The crude product is separated using vacuum filtration equipment and then purified by recrystallization using ethanol to obtain Indole 3 carbinol crystals of high purity. After drying treatment, the final product is obtained.
③Analysis of advantages and disadvantages
The advantages of this method are simple operation, mild reaction conditions, and suitable for laboratory preparation of small quantities. The disadvantage is that its reaction yield is greatly affected by the concentration of formaldehyde and the reaction temperature, and because of the need to use formaldehyde, there may be certain safety and environmental issues.
2. Extraction from plants and chemical modification method
This method is suitable for large-scale production. Especially for industrial production. The idea is to extract natural indole precursor substances from cruciferous plants. For example, indole-3-acetonitrile (Indole-3-Acetonitrile). Then it is converted to Indole 3 carbinol pure powder through a series of chemical reactions.
①Raw material preparation
●Cruciferous plants (e.g. broccoli, cabbage, etc.):
As a source of natural indoles, precursor compounds such as indole-3-acetonitrile can be obtained through extraction.
●Organic solvents (e.g. ethanol, ethyl acetate):
Used in extraction and reaction processes.
●Acid or base catalyst (e.g. sodium hydroxide or sulphuric acid):
Used to promote subsequent reactions.
②Extraction process
●Step 1: Plant Extraction
Cruciferous plant material is dried and crushed, and then indole-3-acetonitrile is extracted by reflux extraction using ethanol or ethyl acetate as solvent. After the extract is filtered and concentrated, the crude extract of indole-3-acetonitrile can be obtained.
●Step 2: Chemical conversion
Dissolve the extracted indole-3-acetonitrile in the appropriate amount of ethanol solvent, and add an acidic catalyst (such as hydrochloric acid or sulfuric acid) to carry out the heating hydrolysis reaction, so that it is converted into Indole 3 carbinol powder. A suitable temperature (60-80°C) is maintained during the reaction and stirred continuously to ensure that the reaction proceeds homogeneously.
The chemical equation of the reaction is given below:
\[ \text{Indole-3-acetonitrile} + H_2O \rightarrow \text{Indole-3-methanol} + \text{NH}_3 \]
Hydrolysis of cyano(-CN) in indole-3-acetonitrile under acidic conditions produces Indole 3 carbinol powder and ammonia.
③ Extraction and purification of the product
●Step 3: Neutralisation and precipitation of products
Upon completion of the reaction, the reaction solution is neutralized to neutrality by the addition of a base (e.g. sodium hydroxide). The mixture is then cooled to room temperature and excess water is added to precipitate the pure Indole 3 carbinol powder. The crude product is isolated using vacuum filtration equipment.
●Step 4: Recrystallisation and purification
The crude product obtained by filtration was dissolved in hot ethanol. It was cooled to room temperature and then recrystallized. The recrystallization process was repeated several times to improve the purity of Indole 3 carbinol 99 powder. Finally, the purified product was dried in a vacuum drier to obtain Indole 3 carbinol with higher purity.
The advantage of this method is that the raw material is natural, widely sourced, and more environmentally friendly. It is especially suitable for large-scale production. Due to the natural plant source, the product has high market recognition and added value. However, the disadvantage is that the extraction process is more complicated.
Problems to pay attention to during the synthesis of Indole 3 carbinol
During the synthesis of Indole 3 carbinol powder, the following issues need to be paid attention to ensure the smooth progress of the reaction and the improvement of product quality:
①Control of reaction conditions
The conditions of temperature, pH and reaction time during the synthesis have a significant effect on the yield and product quality. Especially, too high reaction temperature may lead to the decomposition of Indole 3 carbinol powder, while too low pH may affect the reaction.
② Safety and environmental issues
The use of formaldehyde and other reagents needs to be protected to avoid inhaling formaldehyde vapor. Meanwhile, the organic solvents used in the extraction and reaction process need to be reasonably recycled to reduce the pollution to the environment.
③ Optimisation of the purification process
The purification process of Indole 3 carbinol powder is crucial. Especially in industrial production. Optimization of recrystallization conditions and solvent selection can significantly improve the purity and yield of the product.
Indole 3 carbinol powder is synthesized in a variety of ways. These include chemical synthesis with indoles as starting material extraction from plants and chemical modification. For laboratory studies and small-scale preparation, chemical synthesis offers high operational flexibility and low-cost advantages. For large-scale production, plant extraction to obtain indole precursors for conversion to pure Indole 3 carbinol is more sustainable and marketable. Guanjie Biotech employs advanced extraction and synthesis technologies. Guanjie Biotech uses advanced extraction and synthesis technologies. It can provide high-purity Indole 3 carbinol powder products to meet a wide range of needs for scientific research and industrial applications. And if you want to buy Indole 3 carbinol powder, welcome to enquiry us:info@gybiotech.com.
