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Product Name | Indole-3-acrylic acid |
Cas Number | 16612-40-1 |
Formula | C11H9NO2 |
Molar Mass | 187.19 |
Property1 | Solid at room temperature |
Property2 | Melting point: 214-218°C |
Property3 | Soluble in organic solvents |
Property4 | Slightly soluble in water |
Property5 | White to off-white crystalline powder |
Property6 | Aromatic odor |
Property7 | Used in organic synthesis |
Property8 | Acts as a plant growth regulator |
Property9 | UV-Vis absorbance properties |
Property10 | Chemical stability under normal conditions |
What is the chemical structure of Indole-3-acrylic acid?
Indole - 3 - acrylic acid has the following chemical structure.The chemical structure of Indole - 3 acrylic acid is as follows: It consists of two main parts: an indole ring and an acrylic acid moiety.It is composed of two main parts, an indole moiety and an acrylic acid ring.
The indole ring is a bicyclic heterocyclic compound.The indole is a heterocyclic bicyclic compound. It contains a six - membered benzene ring fused to a five - membered nitrogen - containing pyrrole ring.It contains a six-membered benzene chain fused to a nitrogen-containing pyrrole five-membered ring. In the indole structure, the nitrogen atom in the pyrrole ring has a lone pair of electrons, which can participate in various chemical reactions.In the indole ring structure, the nitrogen atom has a single pair of electrons that can be used in chemical reactions.
Attached to the indole ring at the 3 - position is an acrylic acid group.Acrylic acid is attached to the indole group at the 3 -position. Acrylic acid has the formula CH2=CH - COOH.Acrylic acid is represented by the formula CH2=CH-COOH. The double bond in the acrylic acid part is an important reactive site, enabling the molecule to participate in addition reactions.The double bond of the acrylic acid is a reactive site that allows the molecule to take part in addition reactions. For example, it can react with substances that can add across the double bond, such as hydrogen in the presence of a catalyst to form a saturated derivative.It can, for example, react with substances which can add across the double bonds, such as hydrogen, in the presence a catalyst, to form a saturate derivative.
The carboxyl group (-COOH) in the acrylic acid part is also highly reactive.The carboxyl group in the acrylic acid is also highly reactive. It can undergo acid - base reactions, for instance, donating a proton in the presence of a base to form a carboxylate ion.It can undergo acid-base reactions, such as donating a proton to form a carboxylate in the presence a base. This carboxyl group can also participate in esterification reactions with alcohols to form esters.This carboxyl group is also capable of participating in esterification reactions involving alcohols to produce esters.
The combination of the indole ring and the acrylic acid group in indole - 3 - acrylic acid results in a molecule with unique chemical and biological properties.Indole-3-acrylic acid is a molecule that has unique chemical and biologic properties. The indole part may contribute to certain biological activities related to indole - containing compounds, such as acting as a signaling molecule in some biological systems.The indole component may play a role in certain biological activities associated with indole-containing compounds, including acting as a signaling molecule in some biological systems. The acrylic acid part, with its double bond and carboxyl group, further expands the reactivity and potential applications of the molecule.The acrylic acid portion, with its double-bond and carboxyl groups, increases the reactivity of the molecule and its potential applications. In the field of plant growth regulation, indole - 3 - acrylic acid has been studied for its possible role in promoting plant growth, similar to some other indole - related plant hormones.In the field of plant regulation, indole-3-acrylic acid has been studied to see if it can promote plant growth like other indole-related plant hormones. Overall, its chemical structure endows it with a set of characteristics that make it interesting for both chemical and biological research.Its chemical structure gives it a number of unique characteristics that make it a good candidate for chemical and biological research.
What are the applications of Indole-3-acrylic acid?
Indole - 3 - acrylic acid has several important applications:Indole -3 - acrylic acid is used in many important applications.
1. In agricultureIn agriculture
Indole - 3 - acrylic acid plays a significant role in plant growth regulation.Indole -3 - acrylic acid is a key component in the regulation of plant growth. It can act as a plant growth promoter.It can be used as a plant growth stimulant. Similar to auxins, it can influence various aspects of plant development.It can influence plant development in a similar way to auxins. For instance, it can stimulate root growth.It can, for example, stimulate root growth. By promoting the elongation and branching of roots, plants are better able to absorb water and nutrients from the soil.By encouraging the elongation of roots and their branching, plants are better equipped to absorb soil nutrients and water. This is crucial for the overall health and productivity of crops.This is vital for the overall health of crops and their productivity.
In addition, it can affect plant cell elongation and division.It can also affect cell division and elongation. In the shoots, it may contribute to the proper development of stems and leaves, enhancing photosynthesis efficiency.It may enhance photosynthesis efficiency by promoting the proper development of leaves and stems in the shoots. It can also improve the plant's resistance to environmental stresses.It can also increase the plant's ability to withstand environmental stress. For example, plants treated with indole - 3 - acrylic acid may be more tolerant to drought or salinity, as the improved root system helps in better water and ion uptake under adverse conditions.Plants treated with indole-3-acrylic acid, for example, may be more resistant to drought and salinity because the improved root system allows better water and ion absorption under adverse conditions.
2. In the pharmaceutical fieldIn the pharmaceutical industry
Indole - 3 - acrylic acid has potential biological activities that are of interest in drug development.Indole -3 - acrylic acid may have biological activities that could be of interest to drug developers. It has been studied for its anti - inflammatory properties.Its anti-inflammatory properties have been studied. Inflammation is a key factor in many diseases, including arthritis and some cardiovascular disorders.Inflammation plays a major role in many diseases including arthritis and certain cardiovascular disorders. Compounds with anti - inflammatory capabilities can help in reducing pain and swelling associated with these conditions.Compounds that have anti-inflammatory properties can reduce the pain and swelling caused by these conditions.
Some research also indicates its possible antioxidant effects.Some research has also indicated its possible antioxidant effects. Antioxidants are important in preventing oxidative stress in the body, which can lead to cell damage and the development of diseases such as cancer and neurodegenerative disorders.Antioxidants play a vital role in preventing oxidative stresses in the body. These stressors can cause cell damage and lead to diseases like cancer and neurodegenerative disorders. By scavenging free radicals, indole - 3 - acrylic acid may have a protective role in maintaining cellular health.Indole-3-acrylic acid may protect cells by scavenging harmful free radicals. Additionally, it may have antibacterial and antifungal properties.It may also have antibacterial and/or antifungal properties. These can be useful in the development of new antibiotics or antifungal agents to combat drug - resistant pathogens.These compounds can be used to develop new antifungal or antibiotic agents that will combat drug-resistant pathogens.
3. In the synthesis of other chemicals3.
Indole - 3 - acrylic acid serves as a valuable intermediate in organic synthesis.Indole- 3 – acrylic acid is a valuable organic synthesis intermediate. Its indole and acrylic acid moieties provide reactive sites for further chemical reactions.Its indole- and acrylic-acid moieties serve as reactive sites for subsequent chemical reactions. Chemists can use it to synthesize more complex indole - based compounds.It can be used by chemists to synthesize indole-based compounds that are more complex. These derivatives may have enhanced biological activities or unique physical properties.These derivatives can have unique physical properties or enhanced biological activity. For example, they can be used in the synthesis of dyes, where the indole structure can contribute to the color - forming properties.They can be used to synthesize dyes where the indole structures can contribute to color-forming properties. In the production of specialty polymers, indole - 3 - acrylic acid can be incorporated to impart specific functionality, such as improved biodegradability or enhanced mechanical properties.In the production specialty polymers, it is possible to incorporate indole-3-acrylic acid to impart specific functionality such as improved biodegradability and enhanced mechanical properties.
How is Indole-3-acrylic acid synthesized?
Indole - 3 - acrylic acid can be synthesized through several methods.Indole -3 - acrylic acid is synthesized in several ways. One common approach is via the Knoevenagel condensation reaction.Knoevenagel condensation is a common method.
In this method, indole - 3 - aldehyde serves as a key starting material.In this method, indole-3-aldehyde is the key starting material. It is reacted with malonic acid in the presence of a base catalyst.In the presence of a catalyst, it is reacted to malonic acid. The base catalyst helps to deprotonate the malonic acid, making it more reactive.The base catalyst deprotonates the malonic acid and makes it more reactive. The reaction mechanism involves the nucleophilic attack of the enolate ion (formed from malonic acid) on the carbonyl carbon of indole - 3 - aldehyde.The nucleophilic attack by the enolate (formed from malonic) ion on the carbonyl of indole-3-aldehyde is the mechanism of the reaction. This forms an intermediate.This forms an intermediary. Subsequently, a series of steps occur, including dehydration, which results in the formation of indole - 3 - acrylic acid.Then, a series steps are performed, including dehydration. This results in indole-3-acrylic acid. Pyridine is often used as a base catalyst in this reaction.In this reaction, pyridine is commonly used as a catalyst. The reaction conditions usually require heating the reaction mixture under reflux.The reaction is usually carried out by heating the reaction mixture in reflux. This helps to drive the reaction forward and complete the formation of the desired product.This helps to accelerate the reaction and complete the formation. After the reaction is complete, the product can be isolated and purified.After the reaction has been completed, the product can then be isolated and purified. This typically involves steps such as extraction, where the reaction mixture is treated with an appropriate organic solvent to separate the product from the reaction by - products and unreacted starting materials.This usually involves extraction, in which the reaction mixtures are treated with an organic solvent to separate out the product from reaction by-products and unreacted starter materials. Then, techniques like recrystallization can be employed to further purify the indole - 3 - acrylic acid, obtaining a high - purity product.Recrystallization techniques can be used to further purify indole-3-acrylic acid.
Another possible synthetic route is through the Wittig reaction.The Wittig reaction is another possible route. In this case, an appropriate phosphonium ylide is prepared first.In this case, a suitable phosphonium-ylide must be prepared first. The phosphonium ylide is then reacted with indole - 3 - aldehyde.The phosphonium is then react with indole-3-aldehyde. The reaction proceeds through a [2 + 2] cycloaddition - elimination mechanism.The reaction proceeds via a [2+2] cycloaddition-elimination mechanism. The ylide reacts with the aldehyde to form an oxaphosphetane intermediate.The ylide reacts to form an intermediate oxaphosphetane. This intermediate then decomposes to yield indole - 3 - acrylic acid and a phosphine oxide by - product.This intermediate is then decomposed to yield indole-3-acrylic acid and a by-product of phosphine oxid. The advantage of the Wittig reaction is its high selectivity in forming the carbon - carbon double bond.The Wittig reaction has the advantage of being highly selective in forming carbon-carbon double bonds. However, the preparation of the phosphonium ylide can be somewhat complex and may require careful handling of reagents.The preparation of the phosphonium-ylide is complex and requires careful handling of the reagents. Similar to the Knoevenagel condensation method, after the reaction, the product needs to be isolated and purified using techniques such as extraction and recrystallization to obtain pure indole - 3 - acrylic acid.After the reaction, similar to the Knoevenagel method, the product must be isolated and purified by using techniques such as recrystallization and extraction to obtain pure indole-3-acrylic acid.
What are the properties of Indole-3-acrylic acid?
Indole - 3 - acrylic acid is a significant compound with several notable properties.Indole -3 - acrylic acid has several noteworthy properties.
Physical properties
Indole - 3 - acrylic acid is a solid under normal conditions.Under normal conditions, indole - 3 acrylic acid is solid. It typically appears as a white to off - white crystalline powder.It is usually a white or off-white crystalline powder. This physical state makes it relatively easy to handle and store in laboratory settings.This physical state makes the powder relatively easy to store and handle in laboratory settings. Regarding solubility, it has limited solubility in water.Water is not a good solvent for it. However, it shows better solubility in some organic solvents such as ethanol, methanol, and dimethyl sulfoxide (DMSO).It is more soluble in organic solvents like ethanol, methanol and dimethyl sulfoxide. This solubility behavior is crucial as it allows researchers to dissolve it in appropriate solvents for various applications, whether it is for in - vitro experiments or formulation in certain products.This solubility is important because it allows researchers to dissolve the compound in the appropriate solvents, whether for in-vitro experiments or formulation into certain products.
Chemical properties
The molecule contains an indole ring fused with an acrylic acid moiety.The molecule consists of an indole moiety fused to an acrylic acid moiety. The indole ring imparts aromaticity to the compound, which contributes to its stability.The indole rings impart aromaticity to the compound which contributes to stability. The double bond in the acrylic acid part is reactive, enabling the compound to participate in addition reactions.The double bond of the acrylic acid component is reactive and allows the compound to participate addition reactions. For example, it can undergo Michael addition reactions with suitable nucleophiles.It can undergo Michael additions with nucleophiles. The carboxylic acid group in the structure is acidic.The carboxylic group in the structure has an acidic nature. It can dissociate in aqueous solutions to release a proton, and its pKa value is characteristic of a moderately acidic carboxylic acid functional group.It can dissociate to release a proton in aqueous solution, and its pKa is indicative of a moderately-acidic carboxylic functional group. This acidity allows it to form salts with bases, which can be useful in formulating more water - soluble derivatives for specific applications.This acidity allows the compound to form salts with base, which can be used in formulating more water-soluble derivatives.
Biological properties
Indole - 3 - acrylic acid has shown interesting biological activities.Indole -3 - acrylic acid has demonstrated interesting biological activities. It has been reported to have plant growth - regulating properties.It is reported to have plant growth-regulating properties. In plants, it can act as a phytohormone - like substance.It can act in plants as a phytohormone-like substance. It can influence various plant growth processes such as root elongation, shoot development, and flowering.It can influence plant growth processes like root elongation and shoot development. Some studies suggest that it may interact with the plant's endogenous auxin signaling pathways, although the exact molecular mechanisms are still being investigated.Some studies suggest it may interact with auxin signaling pathways in plants, although the exact molecular mechanism is still being investigated.
In addition, it also exhibits certain antimicrobial properties.It also has antimicrobial properties. It has been found to inhibit the growth of some bacteria and fungi.It has been shown to inhibit the growth and spread of certain bacteria and fungi. The mechanism behind this may involve interfering with the cell membrane integrity or metabolic processes of these microorganisms.This may be due to the fact that it interferes with the cell membrane integrity of these microorganisms or their metabolic processes. This property makes it a potential candidate for natural preservatives in some applications, especially in the food and cosmetic industries where the use of synthetic preservatives is increasingly being scrutinized.This property makes it an ideal candidate for natural preservatives, especially in the cosmetic and food industries where the use synthetic preservatives are increasingly scrutinized.
Overall, the combination of its physical, chemical, and biological properties makes indole - 3 - acrylic acid a compound of great interest in various fields, including plant science, microbiology, and organic synthesis.Indole-3-acrylic acid is a compound that has a combination of physical, chemical and biological properties. It is used in many fields, such as plant science, microbiology and organic synthesis.
What are the potential risks associated with Indole-3-acrylic acid?
Indole - 3 - acrylic acid is a plant - growth regulator and has certain physiological functions in plants.Indole -3 - acrylic acid has physiological functions and is a plant growth regulator. However, like many substances, it may also be associated with some potential risks.Like many substances, there are also some potential risks.
One potential risk is related to its impact on non - target organisms.One potential risk is its impact on organisms that are not the target. Although it is mainly used in the context of plant growth, if it enters the broader ecosystem, it could potentially affect other organisms.It is used primarily to promote plant growth but if it enters a broader ecosystem it could affect other organisms. For example, in soil ecosystems, it might influence the growth and activity of soil microorganisms.In soil ecosystems, for example, it could influence the growth and activity microorganisms. These microorganisms play crucial roles in nutrient cycling, decomposition of organic matter, and maintaining soil structure.These microorganisms are crucial in maintaining soil structure, decomposing organic matter, and cycling nutrients. If indole - 3 - acrylic acid disrupts their normal functions, it could have cascading effects on soil health and plant growth in the long run.If indole-3-acrylic acid disrupts these microorganisms' normal functions, this could have cascading impacts on soil health and plant development in the long term.
When it comes to its application in agriculture, over - use is a significant concern.Over-use is a major concern when it comes to its use in agriculture. If farmers apply excessive amounts of indole - 3 - acrylic acid to promote plant growth, it may lead to abnormal plant development.Farmers who use excessive amounts of indole-3-acrylic acid to promote plant development may cause abnormal plant growth. Instead of the desired enhanced growth and productivity, plants might exhibit distorted growth patterns, such as excessive elongation of stems at the expense of other vital processes like root development.Plants may exhibit distorted growth patterns instead of the desired enhanced productivity and growth, such as excessive stem elongation at the expense other vital processes, like root development. This could make the plants more vulnerable to environmental stresses, such as drought or wind, as they may not have a well - balanced root system to support them.This could make plants more susceptible to environmental stressors, such as wind or drought, because they may not have well-balanced roots to support them.
Another aspect is its potential toxicity to humans.Another aspect is the potential toxicity of indole - 3 - acrylic acid to humans. Although the direct exposure of humans to indole - 3 - acrylic acid is likely to be low in normal agricultural settings, if residues of this substance remain on food crops, there could be implications for human health.In normal agricultural settings, the direct exposure to indole-3-acrylic acid by humans is unlikely to be high. However, if residues remain on food crops then this could have implications for human health. Long - term ingestion of such residues might have unforeseen effects on human metabolism, although as of now, detailed research on the exact human health risks is limited.Ingestion of these residues could have unanticipated effects on human metabolism. However, as of yet, there is little research on the exact risks to human health.
In addition, from an environmental pollution perspective, improper disposal of products containing indole - 3 - acrylic acid or its runoff from agricultural fields can contaminate water bodies.In addition, improper disposal of indole-3-acrylic acid products or its runoff on agricultural fields can contaminate waters. Once in water, it could affect aquatic life.Once it is in the water, it can affect aquatic life. Aquatic plants and animals may be sensitive to this chemical, and changes in their populations or behaviors could disrupt the entire aquatic ecosystem balance.This chemical may affect aquatic plants and animals. Changes in their populations or behavior could disrupt the balance of the aquatic ecosystem.
Overall, while indole - 3 - acrylic acid has useful applications in promoting plant growth, understanding and managing these potential risks is essential to ensure its safe and sustainable use.Indole-3-acrylic acid is useful in promoting plant growth. However, it also poses some risks. Understanding and managing these risks are essential to ensure that its use is safe and sustainable.