.
Product Name | 3-(4-Hydroxy-3-methoxyphenyl)acrylic acid |
Cas Number | 537-73-5 |
Formula | C10H10O4 |
Molar Mass | 194.18 g/mol |
Melting Point | 211-213 °C |
Boiling Point | Not applicable |
Density | 1.34 g/cm³ |
Solubility | Slightly soluble in water |
Pka | 4.43 |
Appearance | White to off-white powder |
Odor | Odorless |
Stability | Stable under recommended storage conditions |
Storage Temperature | Store at room temperature |
Refractive Index | Not applicable |
Flash Point | Not applicable |
Vapor Pressure | Negligible |
What are the applications of 3-(4-Hydroxy-3-methoxyphenyl)acrylic acid?
3-(4-Hydroxy-3-methoxyphenyl)acrylic acid, also known as ferulic acid, has several important applications.
In the field of cosmetics, ferulic acid is highly valued for its antioxidant properties.Ferulic acid's antioxidant properties are highly valued in the cosmetics industry. It can help protect the skin from damage caused by free radicals, which are generated by factors like UV radiation, pollution, and stress.It can protect the skin against damage caused by free-radicals, which are produced by factors such as UV radiation, pollution and stress. By neutralizing these free radicals, it reduces the signs of aging such as wrinkles, fine lines, and age spots.By neutralizing free radicals it reduces signs of aging like wrinkles, fines lines, and age patches. Ferulic acid also has anti - inflammatory properties, making it beneficial for soothing irritated skin.Ferulic acid is also anti-inflammatory, which makes it useful for soothing irritated or rashes skin. It can be incorporated into various skincare products including creams, serums, and sunscreens.It can be used in a variety of skincare products, including creams and serums.
In the food industry, ferulic acid is used as a natural antioxidant.Ferulic acid is a natural antioxidant used in the food industry. It helps to extend the shelf - life of food products by preventing lipid oxidation, which can lead to rancidity.It extends the shelf-life of food products by preventing the oxidation of lipids, which can cause rancidity. It can be added to vegetable oils, baked goods, and meat products.It can be added into vegetable oils, baked goods and meat products. Additionally, ferulic acid has potential health - promoting effects for consumers.Ferulic acid can also have a positive impact on the health of consumers. It may contribute to improved cardiovascular health by reducing oxidative stress and inflammation in the body.It may improve cardiovascular health by reducing inflammation and oxidative stress in the body. It is also found in some whole - grain foods, adding to their nutritional value.It is also present in some whole-grain foods, which adds to their nutritional value.
In the pharmaceutical industry, ferulic acid shows promise in various areas.Ferulic acid is a promising ingredient in the pharmaceutical industry. It has been studied for its potential anti - cancer properties.It has been investigated for its anti-cancer properties. Some research indicates that it may interfere with the growth and spread of cancer cells through mechanisms such as inducing apoptosis (programmed cell death) and inhibiting angiogenesis (the formation of new blood vessels that tumors need to grow).Some research suggests that it may interfere in the growth and spread cancer cells by mechanisms such as causing apoptosis, (programmed death of cells), and inhibiting angiogenesis. Ferulic acid also has neuroprotective effects.Ferulic acid has also been shown to have neuroprotective properties. It may help protect neurons from damage and could potentially be used in the treatment or prevention of neurodegenerative diseases like Alzheimer's and Parkinson's.It could protect neurons from damage, and be used to treat or prevent neurodegenerative diseases such as Alzheimer's and Parkinson's. It can cross the blood - brain barrier, which is essential for its action in the central nervous system.It can cross blood-brain barrier, which is necessary for its action on the central nervous system.
Furthermore, ferulic acid has applications in the agricultural sector.Ferulic acid is also used in agriculture. It can be used as a plant growth regulator.It can be used to regulate plant growth. It may enhance plant growth, improve stress tolerance in plants against factors like drought, salinity, and pathogen attacks.It can enhance plant growth and improve stress tolerance of plants against factors such as drought, salinity and pathogen attacks. This can lead to increased crop yields and better - quality produce.This can lead both to higher crop yields and higher-quality produce.
How is 3-(4-Hydroxy-3-methoxyphenyl)acrylic acid synthesized?
3-(4 - Hydroxy - 3 - methoxyphenyl)acrylic acid, also known as ferulic acid, can be synthesized through several methods. One common approach is the Pechmann condensation.Pechmann condensation is a common method.
In the Pechmann condensation method, vanillin and malonic acid are used as starting materials.Vanillin and malonic acids are used as the starting materials in the Pechmann condensation process. Vanillin contains the 4 - hydroxy - 3 - methoxyphenyl group.Vanillin contains a 4 -hydroxy-3 - methoxyphenyl moiety. Malonic acid provides the acrylic acid moiety.The acrylic acid moiety is provided by malonic acid.
The reaction is typically carried out in the presence of a catalyst.The reaction is usually carried out in presence of a catalyser. A weak base like pyridine is often used.A weak base, such as pyridine, is commonly used. First, vanillin and malonic acid are mixed in an appropriate solvent, such as ethanol.The vanillin and the malonic acid is first mixed in a suitable solvent such as ethanol. The role of the solvent is to dissolve the reactants evenly, facilitating their interaction.The solvent's role is to dissolve the reactants uniformly, facilitating their reaction.
The pyridine catalyst activates the malonic acid.The pyridine catalyst activates malonic acid. Malonic acid, in the presence of pyridine, undergoes a decarboxylation - condensation reaction with vanillin.In the presence of pyridine malonic acid undergoes a condensation-decarboxylation reaction with vanillin. During this process, one of the carboxyl groups of malonic acid is lost as carbon dioxide.During this reaction, one of the malonic acid carboxyl groups is lost in the form of carbon dioxide. The remaining part of malonic acid combines with vanillin to form 3-(4 - hydroxy - 3 - methoxyphenyl)acrylic acid.
The reaction mixture is usually heated under reflux conditions.The reaction mixture is heated in a reflux condition. Heating helps to increase the reaction rate by providing the necessary energy for the chemical bonds to break and reform.Heating increases the rate of reaction by providing energy to break chemical bonds and reform them. Refluxing ensures that the solvent remains in the reaction flask, maintaining a constant reaction environment.Refluxing keeps the solvent in the reaction flask and maintains a constant reaction.
After the reaction is complete, the product can be isolated.After the reaction has finished, the product is isolated. This often involves techniques such as filtration if there are any insoluble by - products.If there are any insoluble products, this can be done using techniques like filtration. The crude product can then be purified.The crude product is then purified. Purification methods may include recrystallization.Recrystallization is one method of purification. Recrystallization is carried out by dissolving the crude product in a suitable hot solvent, such as ethanol - water mixture.Recrystallization can be carried out by dissolving crude product in a hot solvent such as an ethanol-water mixture. As the solution cools, pure 3-(4 - hydroxy - 3 - methoxyphenyl)acrylic acid crystallizes out, leaving impurities in the solution. The crystals can be collected by filtration and dried to obtain the final pure product.The crystals are collected by filtration, and then dried to obtain a pure product.
Another method for synthesizing 3-(4 - hydroxy - 3 - methoxyphenyl)acrylic acid is by the hydrolysis of its esters. If an ester derivative of 3-(4 - hydroxy - 3 - methoxyphenyl)acrylic acid is available, hydrolysis in the presence of an acid or a base can convert it to the free acid. For example, in an alkaline hydrolysis, the ester is treated with an aqueous solution of sodium hydroxide.In an alkaline reaction, the ester can be treated with a solution of sodium hydroxide in water. The reaction breaks the ester bond, liberating the carboxylic acid group and forming the sodium salt of 3-(4 - hydroxy - 3 - methoxyphenyl)acrylic acid. Subsequent acidification with a strong acid like hydrochloric acid converts the sodium salt back to the free acid, which can then be isolated and purified as described above.The sodium salt can be converted back to the free acrylic acid by acidification with hydrochloric or other strong acids.
What are the physical and chemical properties of 3-(4-Hydroxy-3-methoxyphenyl)acrylic acid?
3-(4-Hydroxy-3-methoxyphenyl)acrylic acid, also known as ferulic acid, has several notable physical and chemical properties.
Physical properties:Physical Properties
In terms of appearance, ferulic acid is typically a yellowish - brown crystalline powder.Ferulic acid appears as a powdery yellowish-brown color. It has a characteristic odor.It has a distinctive odor. The melting point of ferulic acid is around 174 - 176 degC.The melting point for ferulic is between 174 and 176 degrees Celsius. This relatively high melting point is due to the presence of strong intermolecular forces such as hydrogen bonding.This high melting point is due in part to strong intermolecular forces, such as hydrogen bonds. The hydrogen bonding can occur between the hydroxyl groups of different molecules.Hydrogen bonding can take place between the hydroxyl groups in different molecules. Ferulic acid is sparingly soluble in water.Ferulic acid dissolves sparingly in water. This is because while it has polar functional groups like the hydroxyl and carboxyl groups that can potentially interact with water through hydrogen bonding, the large non - polar aromatic ring part of the molecule dominates, making it less soluble in the highly polar water solvent.It is less soluble in water because, while it contains polar functional groups such as hydroxyl and carboxyl, which can interact with water via hydrogen bonds, the non-polar aromatic ring dominates the molecule. However, it shows better solubility in polar organic solvents such as ethanol, methanol, and dimethyl sulfoxide (DMSO).It is more soluble in polar organic solutions such as ethanol (methanol), dimethyl sulfoxide, and DMSO.
Chemical properties:Chemical properties
Ferulic acid contains multiple reactive functional groups, which endow it with rich chemical reactivity.Ferulic acid is a highly reactive chemical compound due to its multiple reactive functional groups. The carboxyl group (-COOH) at one end of the molecule is acidic.The carboxyl group at the one end of a molecule is acidic. It can participate in acid - base reactions, donating a proton to form carboxylate anions in the presence of a base.It can participate in acid-base reactions by donating a proton in the presence a base to form carboxylate ions. This property allows ferulic acid to form salts with metal hydroxides or amines.This property allows the ferulic to form salts when combined with metal hydroxides and amines. For example, reacting with sodium hydroxide will produce the corresponding sodium ferulate salt.Reacting with sodium hydroxide, for example, will produce the sodium ferulate salt. The hydroxyl group (-OH) on the aromatic ring is also reactive.The hydroxyl group on the aromatic ring (-OH) is also reactive. It can be involved in esterification reactions.Esterification reactions can involve it. When reacted with carboxylic acids or acid anhydrides in the presence of a catalyst, it can form esters.It can be converted to esters when it reacts with carboxylic acid or acid anhydrides, in the presence a catalyst. This is useful in the synthesis of ferulic acid derivatives for various applications.This can be used to synthesize ferulic acids derivatives that are useful for a variety of applications. The double bond in the acrylic acid part of the molecule is unsaturated, enabling ferulic acid to undergo addition reactions.The double bond of the acrylic acid portion of the molecule, which is unsaturated allows ferulic to undergo addition reactions. For instance, it can react with bromine in an addition reaction across the double bond, adding bromine atoms to the molecule.It can, for example, react with bromine to add bromine atoms across the double-bond. Ferulic acid also has antioxidant properties.Ferulic acid has antioxidant properties. The phenolic hydroxyl group on the aromatic ring can donate a hydrogen atom to scavenge free radicals, converting the molecule into a relatively stable phenoxy radical.The phenolic group on the aromatic ring is able to donate a hydrogen atom in order to scavenge radicals. This converts the molecule into the relatively stable phenoxyradical. This ability to inhibit oxidative processes makes it valuable in the food, cosmetic, and pharmaceutical industries.Its ability to inhibit oxidative reactions makes it a valuable ingredient in the food, pharmaceutical, and cosmetic industries.
Is 3-(4-Hydroxy-3-methoxyphenyl)acrylic acid safe to use?
3-(4-Hydroxy-3-methoxyphenyl)acrylic acid, also known as ferulic acid, has several aspects regarding its safety.
Firstly, in terms of oral intake, ferulic acid is generally regarded as safe when consumed in the amounts typically found in the diet.First, ferulic acids are generally considered safe for oral intake when consumed in amounts that are typical of a diet. It is present in various foods such as grains, fruits, and vegetables.It is found in many foods, including grains, fruits and vegetables. For example, it is abundant in rice bran, oats, and wheat.It is found in rice bran and oats. In food applications, it has been used for its antioxidant properties to help preserve food and prevent lipid oxidation.It has been used in food applications for its antioxidant properties. This helps preserve food and prevents lipid oxidation. When consumed as part of a normal diet, it is well - tolerated by the body and has not been associated with significant adverse effects.It is well-tolerated by the body when consumed as part a normal diet and has not been linked with significant adverse effects.
Secondly, in the context of skincare products, ferulic acid is a popular ingredient.Second, ferulic is a very popular ingredient in skincare products. It can help protect the skin from damage caused by free radicals, which are associated with premature aging, sun damage, and skin inflammation.It can protect the skin against damage caused by free-radicals, which is associated with premature skin aging, sun damage and skin inflammation. It has been extensively studied for its potential in improving skin texture, reducing hyperpigmentation, and enhancing the effectiveness of other antioxidants like vitamin C and E. In well - formulated skincare products, it is considered safe for most skin types.It has been extensively researched for its potential to improve skin texture, reduce hyperpigmentation and enhance the effectiveness of other anti-oxidants like vitamin C and Vitamin E. In well-formulated skincare products, this ingredient is considered safe for all skin types. However, as with any skincare ingredient, some individuals may be sensitive or allergic to it.As with any skincare product, some people may be allergic or sensitive to it. Symptoms of an allergic reaction could include redness, itching, or swelling of the skin.An allergic reaction can cause redness, itchiness, or swelling. It is always advisable for those with sensitive skin to perform a patch test before widespread use.For those with sensitive skin, it is best to test the product on a small area before using it more widely.
Finally, in terms of potential interactions, ferulic acid may interact with certain medications.Ferulic acid can interact with certain medications. Since it has antioxidant and anti - inflammatory properties, it could potentially interact with blood - thinning medications or drugs that affect the immune system.It could interact with drugs that affect the immune or blood thinning systems due to its anti-inflammatory and antioxidant properties. People who are taking prescription medications should consult their healthcare provider before starting to use products containing high amounts of ferulic acid, whether orally or topically.If you are taking prescription medication, consult your healthcare provider before using products that contain high levels of ferulic acids, either orally or topically.
Overall, 3-(4 - Hydroxy-3 - methoxyphenyl)acrylic acid is generally safe for use, whether in dietary or skincare applications. But proper precautions, such as patch testing for skincare use and consulting a doctor for those on medications, should be taken to ensure individual safety.To ensure safety, it is important to take the proper precautions. For example, patch testing should be done for skincare and a consultation with a doctor should be made for those taking medications.
What are the storage and handling requirements for 3-(4-Hydroxy-3-methoxyphenyl)acrylic acid?
3-(4-Hydroxy-3-methoxyphenyl)acrylic acid, also known as ferulic acid, has specific storage and handling requirements.
For storage, it should be kept in a cool, dry place.It should be stored in a dry, cool place. High temperatures can accelerate chemical reactions and potentially degrade the compound.High temperatures can accelerate chemistry and degrade the compound. A storage temperature between 2 - 8degC is often ideal for long - term preservation in a laboratory or industrial setting.In a laboratory or industrial environment, a temperature range of 2-8degC can be ideal for long-term preservation. If stored at room temperature, it should be in an area away from direct sunlight and heat sources like radiators or hot equipment.Stored at room temperature it should be kept away from heat sources such as radiators and hot equipment. Exposure to sunlight can cause photochemical reactions that may change the structure or properties of ferulic acid.The sun can cause photochemical reactions which may alter the structure or properties.
The storage container is also crucial.The storage container plays a crucial role. It should be made of a material that is chemically inert to ferulic acid.It should be made from a material which is chemically inert towards ferulic acids. Glass containers are commonly used as they do not react with the compound easily.Glass containers are used because they do not react easily with the compound. However, if using plastic containers, ensure they are made of materials like high - density polyethylene (HDPE) which has good chemical resistance.If you are using plastic containers make sure they are made from materials such as high-density polyethylene (HDPE), which is chemically resistant. The container should be tightly sealed to prevent moisture absorption.The container must be tightly sealed to avoid moisture absorption. Ferulic acid can be hygroscopic, and excessive moisture can lead to clumping or even chemical changes such as hydrolysis in some cases.Ferulic acid is hygroscopic and excessive moisture may cause clumping, or even chemical reactions such as hydrolysis.
During handling, personal protective equipment (PPE) is essential.Personal protective equipment (PPE), such as gloves, is vital when handling. Gloves made of materials like nitrile should be worn to prevent skin contact.Wearing gloves made from materials such as nitrile will help prevent skin contact. Ferulic acid may cause skin irritation, and repeated or prolonged contact can lead to more serious skin problems.Ferulic acid can cause irritation to the skin. Repeated or prolonged contact may lead to more serious problems. Safety goggles should also be worn to protect the eyes in case of any splashes.Wear safety goggles to protect your eyes from any splashes. If the compound is in powder form, a dust mask should be used to avoid inhalation.Dust masks should be worn if the compound is powdered to prevent inhalation. Inhalation of ferulic acid dust may cause respiratory irritation.Inhalation of dust containing ferulic acids can cause respiratory irritation.
When weighing or measuring ferulic acid, use clean and dry instruments.Use clean and dry instruments when weighing or calculating ferulic acids. Contamination from other substances can affect the purity and properties of the compound.Contamination by other substances can affect purity and properties. For example, if the weighing scale has residues from other chemicals, it can lead to inaccurate measurements and possible chemical interactions.If the weighing scale contains residues of other chemicals, this can lead to inaccurate readings and possible chemical reactions.
In case of spills, immediate action is required.If spills occur, immediate action must be taken. First, ensure the area is well - ventilated.Ensure the area is well-ventilated. For small spills of the solid, carefully sweep it up using a clean, dry brush and place it in a proper waste container.Use a dry, clean brush to carefully sweep up small spills. Place them in the appropriate waste container. If it's a liquid spill, absorb it with an appropriate absorbent material like vermiculite or activated charcoal, and then dispose of the absorbent according to local regulations.If the liquid spill is large, use an absorbent material such as vermiculite, activated charcoal or a similar absorbent. Dispose of the absorbent in accordance with local regulations.