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3-Indoleacrylic acid is an organic compound with the molecular formula C12H9NO2, CAS 1204-06-4, and a relative molecular weight of 199.21g/mol. Commonly white to light yellow powdery crystals, and colorless crystals with high purity. There is a strong absorption peak in the ultraviolet region, with wavelengths ranging from 220-250nm. Easy to dissolve in organic solvents but difficult to dissolve in water, with a melting point of 175-177 ℃ and a density of 1.365 g/mL (25 ℃). Its fluorescence spectrum is related to the pH value of the solution, has good stability, and can be stored for a long time at room temperature. In addition, 3 Indoleacrylic acid is toxic to the human body and should be used safely. It has various pharmacological effects, including anti-tumor, anti-inflammatory, antibacterial, and immune regulation. These effects have broad application prospects in fields such as medicine, health products, and food.
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Chemical Formula |
C11H9NO2 |
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Exact Mass |
187 |
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Molecular Weight |
187 |
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m/z |
187 (100.0%), 188 (11.9%) |
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Elemental Analysis |
C, 70.58; H, 4.85; N, 7.48; O, 17.09 |
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3-Indoleacrylic acid, also known as indoleacrylic acid, is a biologically active compound that mainly exists in plants and animals in nature. It has multiple potential pharmacological effects, including anti-tumor, anti-inflammatory, antibacterial, and immune regulation.
1. Anti tumor effect:
3 Indoleacrylic acid has significant anti-tumor activity. It can inhibit the growth and proliferation of tumor cells, induce tumor cell apoptosis, and inhibit tumor angiogenesis. These effects help to reduce the invasion and metastasis ability of tumor cells. Research has shown that 3 Indoleacrylic acid can exert anti-tumor effects by regulating various signaling pathways and molecular targets, such as inhibiting protein kinase C and inducing cell cycle arrest.
2. Anti inflammatory effect: 3 Indoleacrylic acid has significant anti-inflammatory effects. It can inhibit the release of various cytokines and inflammatory mediators in the inflammatory response, thereby alleviating the inflammatory response. Research has shown that 3 Indoleacrylic acid can inhibit nuclear factors by κ B (NF- κ B) And signaling pathways such as mitogen activated protein kinase (MAPK) exert anti-inflammatory effects.
3. Antibacterial effect: 3- ndoleacrylic acid has a certain antibacterial effect. It can inhibit the growth and reproduction of various bacteria and fungi, such as Escherichia coli, Staphylococcus aureus, Candida albicans, etc. Research has shown that 3 Indoleacrylic acid can exert antibacterial effects by disrupting cell membranes and inhibiting the activity of intracellular enzymes.
4. Immunomodulatory effect: 3 Indoleacrylic acid has a certain immune regulatory effect. It can regulate the functions of various immune cells, such as inhibiting inflammatory reactions and promoting the secretion of cytokines. Research has shown that 3 Indoleacrylic acid can exert immune regulatory effects by regulating receptors and signaling pathways on the surface of immune cells.
5. Inhibition of inflammatory response: 3 Indoleacrylic acid can inhibit the release of various inflammatory mediators during the inflammatory response process, such as prostaglandin E2 (PGE2), nitric oxide (NO), and tumor necrosis factor- α (TNF- α), Interleukin-1 β (IL-1 β) Etc. Research has shown that it can inhibit nuclear factors κ B (NF- κ B) The activation of signaling pathways such as mitogen activated protein kinase (MAPK) reduces the production of inflammatory mediators, thereby alleviating the inflammatory response.
6. Regulating immune cell function: 3 Indoleacrylic acid can affect the function of various immune cells. Research has shown that it can inhibit the proliferation of T lymphocytes and the secretion of cytokines, and has a regulatory effect on the differentiation of T helper cell 1 (Th1) and T helper cell 2 (Th2). In addition, 3 Indoleacrylic acid can also inhibit the killing activity of natural killer cells (NK cells), playing an important role in the balance and function of immune cells.
7. Anti allergic reactions: 3 Indoleacrylic acid has an anti allergic effect. It can inhibit the immune response induced by allergens and reduce the occurrence of allergic symptoms. Research has shown that it can inhibit the release of histamine and have antagonistic effects on histamine receptors, thereby reducing allergic reactions.
8. Inhibition of autoimmune diseases: 3 Indoleacrylic acid has a certain inhibitory effect on autoimmune diseases. Research has shown that it can inhibit the occurrence and development of experimental autoimmune encephalomyelitis (EAE), and also has a certain inhibitory effect on experimental autoimmune hepatitis (EAH). These effects are closely related to inhibiting inflammatory reactions and regulating immune cell function.
In summary, 3 Indoleacrylic acid has various uses in immune regulation, including inhibiting inflammatory reactions, regulating immune cell function, anti allergic reactions, and inhibiting autoimmune diseases. These effects have potential application value in the treatment and prevention of immune related diseases. In the future, further research on its mechanism of action and pharmacokinetic characteristics can provide more theoretical basis and practical support for its development.
Chemical Properties and Basic Structure
3-Indoleacrylic Acid (chemical formula: C₁₁H₉NO₂, CAS number: 1204-06-4) is an α,β-unsaturated monocarboxylic acid. Its structure is formed by the conjugation of the acrylic acid backbone and the indole-3-group. This compound typically appears as a light yellow to brownish crystalline powder, with a density of approximately 1.196 g/cm³. In terms of solubility, it can reach 50 mg/mL in DMSO (requires ultrasonic assistance for dissolution), but has relatively low solubility in water or ethanol. Its stability is significantly affected by temperature and light, and it needs to be stored for a long time at -20℃ (powder) or -80℃ (solvent). During transportation, it should be packaged with blue ice or kept in a light-proof container at room temperature.
Core Manufacturing Process
The synthesis route of 3-Indoleacrylic Acid mainly consists of multiple reactions. The key steps involve functional group modification of the indole ring and the introduction of the acrylic structure. The following is a typical process flow:
Initial raw material selection
Common starting materials include indole-3-carboxaldehyde or indole-3-carboxylic acid. Taking indole-3-carboxaldehyde as an example, it reacts with malonic acid in acetonitrile under reflux for 9 hours, and through the Knoevenagel condensation reaction, an intermediate 3-indole propenoyl ester is formed. Subsequently, it is hydrolyzed to obtain the target product. The total yield of this route is approximately 60%-70%, but the reaction temperature needs to be strictly controlled (80-90℃) to avoid the formation of by-products.
Optimization of the catalytic system
To improve the reaction efficiency, researchers developed a one-pot two-step synthesis process:
The first step: 3-Indoleacrylic Acid (1 mmol), phenol (1.5 mmol), and potassium carbonate (0.2 mmol) are mixed in DMF, and stirred at 100℃ for 1 hour. Through the Michael addition reaction, a sulfur ether intermediate is generated.
The second step: The intermediate undergoes in-situ dehydrogenation to form 3-[1-(phenylthio)ethyl]-1H-indole, with a total yield of up to 98%. This method promotes the reaction through a catalytic amount of base (K₂CO₃), avoiding the use of heavy metal catalysts in traditional processes, which is in line with the green chemistry trend.
Purification and quality control
The crude product needs to be purified by flash chromatography, using silica gel as the stationary phase and dichloromethane/methanol (9:1) as the eluent. After purification, the product needs to be identified by HPLC (≥98%) and NMR (¹H/¹³C) to ensure it meets the standards for biological experiments or industrial production. For example, the product specification provided by a certain supplier shows that its purity is 99.62%, and the residual solvent (DMF) is less than 0.1%.
Considerations for industrial-scale production
Scale-up challenges
There are significant differences between laboratory synthesis and industrial production. For instance, when a company attempted to scale up the one-pot method to 10 kg level, it was found that the heat transfer in the reactor was uneven, resulting in local overheating, and the proportion of by-products increased to 15%. Solutions include:
Replacing the traditional batch reactor with a continuous flow reactor, and enhancing mass transfer and heat transfer through microchannel design;
Optimizing the solvent system, using low-boiling-point solvents (such as acetonitrile) instead of DMF, to reduce processing energy consumption.
Cost control and raw material supply
The market price of 3-Indoleacrylic Acid fluctuates significantly. For example:
The price of high-purity (99.62%) product is up to $30/mg (TargetMol), mainly used for scientific research;
The industrial grade (99%) product can be as low as $3/kg (an import-export company in Hebei), suitable for large-scale production.
The raw material cost accounts for approximately 40%, with the price of indole-3-carboxaldehyde being significantly affected by the upstream aniline market. Enterprises need to lock in supply through long-term contracts.
Environment and safety
The waste liquid produced during the production process contains organic solvents (such as DMF, dichloromethane) and acidic/basic waste. It needs to be recovered through distillation and neutralization before being discharged. Additionally, 3-Indoleacrylic Acid itself has a mild irritant property, and operators need to wear protective equipment, and the production workshop needs to maintain ventilation.
Application fields and manufacturing orientation
Biomedical research
As a metabolite of tryptophan, 3-Indoleacrylic Acid is widely used in intestinal microbiota research. For example, it can inhibit the expression of inflammatory factors (such as IL-6, TNF-α), protecting the intestinal epithelial barrier function. The manufacturing end needs to provide isotope markers (such as 3-Indoleacrylic Acid-d₄), which are used for metabolic pathway tracking. The price of such products is usually 2-3 times that of the ordinary type.
Agriculture and Materials Science
Recent research has found that 3-Indoleacrylic Acid has strong anti-algae activity and can inhibit the synthesis of algal cell membranes. To meet the needs of agricultural spraying, the manufacturing process needs to optimize the water solubility of the product (such as through salt formation or nano-coating), while reducing the production cost to below $1/kg.
Customized Services
Some companies offer structural modification services, such as introducing fluorine, chlorine, etc. as substituents on the indole ring to enhance the biological activity of the target molecule. The cycle for such customized synthesis is usually 4-6 weeks, with a MOQ (Minimum Order Quantity) of 10 grams, and the price fluctuates according to complexity.
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