Pure indole 3 carbinol and 3,3'-diindolylmethane powder are two natural plant compounds derived from cruciferous vegetables. DIM and indole 3 carbinol have significant differences in structure, properties, and applications. The following is a detailed analysis of multiple aspects.
Source and generation mechanism
Both I3C and DIM come from cruciferous vegetables, and their generation process is as follows.
The precursor contained in plants is glucobranconin. When plant cells are destroyed, glucobranconin generates indole-3-carbinol (I3C) under the action of myrosinase.
I3C further polymerizes in the gastric acid environment to form DIM and other derivatives.
Difference analysis: I3C is released directly from vegetables through enzymatic reactions, while DIM requires I3C to be converted in an acidic environment.
Molecular structure
●Indole-3-carbinol
The molecular formula of indole-3-carbinol is C9H9NO. Its molecule consists of an indole ring and a carbinol group (-CH2OH) connected to the 3rd position. The indole ring is a nitrogen-containing aromatic heterocycle. It is composed of a benzene ring and a pyrrole ring fused and has unique aromaticity and electron cloud distribution. The carbinol group is connected to the carbon atom at the 3rd position of the indole ring through a carbon-carbon bond. The hydroxyl (-OH) molecule in the carbinol group has certain polarity and hydrophilicity.
●Diindolylmethane
The molecular formula of diindolylmethane is C18H14N2. It is formed by two indole molecules bridged by a methylene (-CH2-). The two indole rings are connected to their respective carbon atoms at the 3rd position through the carbon atoms of the methylene. Therefore, it forms a relatively large molecular structure with a certain symmetry. Since the molecule does not contain a strong polar group such as a hydroxyl group, the overall molecular polarity is relatively weak.
Physical properties
1.Appearance
•Indole-3-carbinol:
Pure indole 3 carbinol is usually a white to light yellow crystalline powder. Under the microscope, its crystals have a certain shape and regularity.
•Diindolylmethane:
Diindolylmethane is also generally a white to light yellow powder. However it may be slightly different from indole-3-carbinol in appearance, and the fineness and aggregation state of its powder may be different.
Bulk indole-3-carbinol and diindolylmethane produced by Guanjie Biotech are whiter in color than other companies. This is our product advantage. If you need, we can provide free samples. Please email at info@gybiotech.com.
2.Melting point
•Indole-3-carbinol:
The melting point of indole-3-carbinol is relatively low, about 95-98℃. This is due to the presence of hydroxyl groups in its molecules, which can form hydrogen bonds between molecules. Therefore, the intermolecular force is relatively strong, but it does not require high energy to destroy the lattice like some substances with complex lattice structures. So the melting point is at a medium level.
•Diindolylmethane:
The melting point of DIM is relatively high, generally around 124-126℃. Although there are no hydrogen bonds formed by strong polar groups in its molecular structure, the Van der Waals forces between molecules are large due to the large size and certain rigidity of the molecules. It requires a higher temperature for the molecules to overcome these forces and melt.
3.Solubility
•Indole-3-carbinol:
Pure indole 3 carbinol is slightly soluble in water. The presence of hydroxyl groups makes it hydrophilic. However, the hydrophobicity of the indole ring limits its solubility in water. It can be well dissolved in some organic solvents. Such as ethanol, carbinol, dichloromethane, etc. In these solvents, molecules and solvent molecules can interact through hydrogen bonds or Van der Waals forces to achieve dissolution.
•Diindolylmethane:
Diindolylmethane powder has very low solubility in water and is almost insoluble in water. This is because its overall non-polarity is strong. Its solubility in organic solvents is different from that of indole-3-carbinol. It has good solubility in some non-polar or weakly polar organic solvents such as benzene, toluene, chloroform, etc., but its solubility in organic solvents with greater polarity such as carbinol is relatively poor.
Chemical properties
1.Reaction sites
•Indole-3-carbinol:
The hydroxyl group in its molecule has a certain activity. Indole-3-carbinol can undergo a variety of chemical reactions. The hydroxyl group can be oxidized to aldehyde, carboxyl, etc., and can also participate in esterification reactions and react with acids to form corresponding esters. In addition, the double bonds and nitrogen atoms on the indole ring also have certain reactivity and can undergo electrophilic substitution reactions.
•Diindolylmethane:
Its reactivity is mainly concentrated on the double bonds and nitrogen atoms on the indole ring. 3 3 diindolylmethane supplement can undergo some typical reactions of indole compounds. Such as electrophilic substitution reactions. However, due to the bridging effect of the methylene group, there will be a certain mutual influence between the two indole rings. Its reactivity and selectivity are different from those of a single indole molecule.
2.Stability
•Indole-3-carbinol:
The stability of pure indole-3-carbinol is slightly poor. Especially in some oxidizing environments, the hydroxyl group is easily oxidized. This leads to changes in the molecular structure. Under acidic or alkaline conditions, some hydrolysis or other reactions may also occur, affecting its stability.
•Diindolylmethane:
Organic DIM supplement has relatively good stability. There are no active groups in the molecule that are easily oxidized or reacted with other reactions, such as hydroxyl groups. Under normal environmental conditions, the molecular structure of diindolylmethane powder is relatively stable. However, under some extreme conditions such as strong acidity, strong alkalinity, high temperature, and high pressure, decomposition or other reactions may also occur.
Synthesis method
1.Synthesis of indole-3-carbinol
•Extraction from natural products:
Some cruciferous vegetables are rich in precursors of indole-3-carbinol. Pure Indole 3 carbinol supplement can be obtained from these vegetables through a series of extraction, separation, and conversion processes. First, the vegetables are crushed, extracted, and other operations are performed to obtain a crude extract containing relevant components. Then, using separation techniques such as column chromatography and high-performance liquid chromatography, we separate and purify the crude extract. Finally, the precursor is converted into broccoli indole 3 carbinol through chemical conversion and other methods.
•Chemical synthesis method:
Using indole as a raw material, indole-3-carbinol can be synthesized by reacting with reagents such as formaldehyde under certain reaction conditions, and then undergoing reduction and other steps. For example, under alkaline conditions, indole and formaldehyde undergo a condensation reaction to generate an intermediate product. The intermediate product is then reduced with a reducing agent such as sodium borohydride to obtain indole-3-carbinol.
2.Synthesis of diindolylmethane
•Using indole and formaldehyde as raw materials:
Under the action of an acidic catalyst, indole and formaldehyde undergo a condensation reaction. Two indole molecules are linked together by a methylene bridge to generate DIM 3.3 diindolylmethane. Commonly used acidic catalysts include hydrochloric acid and sulfuric acid, and the reaction is usually carried out in an organic solvent. Such as ethanol, dichloromethane, etc. During the reaction, it is necessary to control the reaction temperature, the ratio of reactants, and the reaction time to improve the yield and purity of the product.
•Synthesis using other methods:
Pure DIM supplement can also be prepared by some other organic synthesis methods. For example, indole derivatives are reacted with reagents containing methylene under specific reaction conditions, or the molecular structure of 3 3 diindolylmethane powder is constructed by some transition metal-catalyzed reactions.
Biological activity and metabolic process
1. Indole 3 carbinol Benefits
Indole 3 carbinol powder can induce cell apoptosis and inhibit cancer cell proliferation.
I3C can regulate estrogen metabolism, promote the conversion of estrogen from 16α-hydroxyestrone to 2-hydroxyestrone, and reduce the risk of hormone-related cancers.
Organic indole 3 carbinol can regulate NF-κB and PI3K/Akt pathways and has anti-inflammatory and immunomodulatory effects.
Metabolic process: I3C is converted into DIM, Indole[3,2-b]carbazole (ICZ) and Cyanohydroxyindole (CHI) in the stomach, and these metabolites jointly exert biological activity.
2. Biological activity of DIM
•DIM is the main active metabolite of I3C, and its activity is more stable and lasting.
•DIM powder supplement has anti-tumor, anti-inflammatory and immune-regulating effects.
•DIM can regulate estrogen metabolism and promote the production of 2-hydroxyestrone.
•Diindolylmethane DIM powder can exert its effects by activating the AhR pathway, inhibiting mTOR signaling and regulating intestinal microbiota.
Difference analysis: I3C is the precursor of multiple active metabolites, while best quality DIM supplement is the main and stable active ingredient with clearer biological activity.
Pure indole 3 carbinol is the precursor of DIM. Both have anti-cancer, immunomodulatory and hormone-balancing effects. The activity of I3C depends on its conversion in gastric acid. As the main metabolite, DIM has more stable biological activity and is more widely used in clinical practice. If you choose a of indole 3 carbinol powder supplier or a 3 3 Diindolylmethane powder manufacturer, welcome to consider Guanjie Biotech. Our products pass HALAL, HACCP, ISO90001, KOSHER and others. Welcome to enquiry info@gybiotech.com.
