A Review of Chalcone Synthesis from Acetophenone and Benzaldehyde and Its Biological Activities
Synthesis of Chalcone from Acetophenone and Benzaldehyde PDF Download
If you are interested in organic chemistry, you might have heard of chalcone. Chalcone is a simple aromatic ketone that has a wide range of applications in various fields. In this article, you will learn how to synthesize chalcone from acetophenone and benzaldehyde, two common organic compounds. You will also learn about the results, characteristics, and properties of chalcone, as well as its uses and benefits. Finally, you will find a link to download the PDF file of the synthesis procedure for your convenience.
Synthesis Of Chalcone From Acetophenone And Benzaldehyde Pdf Download
Introduction
What is chalcone?
Chalcone is an organic compound that belongs to the class of flavonoids. Flavonoids are natural substances that are widely distributed in plants and fruits. They are responsible for the color, flavor, and aroma of many plants. Chalcone has the general formula C15H12O, which can be written as (C6H5)2C=CH-CO-CH3. It consists of two benzene rings connected by a three-carbon chain that contains a double bond and a ketone group.
Why is chalcone important?
Chalcone is important because it serves as an intermediate for the synthesis of many other flavonoids. Flavonoids have various biological activities, such as antioxidant, anti-inflammatory, anticancer, antimicrobial, antiviral, antidiabetic, and neuroprotective effects. Therefore, chalcone can be used to produce many useful compounds for pharmaceutical, cosmetic, food, and agricultural industries. Moreover, chalcone itself has some interesting properties that make it valuable for research and development.
Procedure
Materials and equipment needed
To synthesize chalcone from acetophenone and benzaldehyde, you will need the following materials and equipment:
Acetophenone (C8H8O)
Benzaldehyde (C7H6O)
Sodium hydroxide (NaOH)
Ethanol (C2H6O)
Ice
Water
Filter paper
Round-bottom flask
Magnetic stirrer and stir bar
Reflux condenser
Heating mantle
Vacuum filtration apparatus
Melting point apparatus
Infrared spectrometer
Nuclear magnetic resonance spectrometer
Step-by-step instructions
Here are the step-by-step instructions for the synthesis of chalcone from acetophenone and benzaldehyde:
In a round-bottom flask, add 10 mL of ethanol, 2.5 g of acetophenone, and 2.1 g of benzaldehyde. Stir the mixture well with a magnetic stirrer.
Add 2.5 g of sodium hydroxide to the flask and stir until it dissolves completely.
Attach a reflux condenser to the flask and place it on a heating mantle. Heat the mixture under reflux for 2 hours. The reflux temperature should be around 80C.
After 2 hours, remove the flask from the heating mantle and let it cool down to room temperature.
Pour the mixture into a beaker containing 100 mL of ice water. Stir the mixture vigorously to precipitate the chalcone crystals.
Collect the chalcone crystals by vacuum filtration using a filter paper. Wash the crystals with cold water and ethanol to remove any impurities.
Dry the chalcone crystals in an oven at 50C for 30 minutes.
Weigh the chalcone crystals and calculate the percentage yield. The theoretical yield is 3.8 g, so the percentage yield is (actual yield / theoretical yield) x 100%.
Determine the melting point of the chalcone crystals using a melting point apparatus. The expected melting point is around 95C.
Analyze the chalcone crystals using infrared spectroscopy and nuclear magnetic resonance spectroscopy. Compare the spectra with the literature values and identify the functional groups and protons present in chalcone.
Safety precautions and tips
Here are some safety precautions and tips to follow when performing the synthesis of chalcone from acetophenone and benzaldehyde:
Wear appropriate personal protective equipment, such as gloves, goggles, lab coat, and shoes.
Handle acetophenone and benzaldehyde with care, as they are flammable and irritant liquids. Avoid contact with skin, eyes, and clothing. Use them in a well-ventilated area or a fume hood.
Handle sodium hydroxide with care, as it is a corrosive solid. Avoid contact with skin, eyes, and clothing. Use it in a well-ventilated area or a fume hood.
Handle ethanol with care, as it is a flammable and toxic liquid. Avoid contact with skin, eyes, and clothing. Use it in a well-ventilated area or a fume hood.
Avoid inhaling or ingesting any of the materials or products used or obtained in this experiment.
Clean up any spills or leaks immediately using appropriate methods and materials.
Dispose of any waste materials according to local regulations and guidelines.
Results
Physical appearance and structure of chalcone
The chalcone crystals obtained from this experiment are yellow in color and have a needle-like shape. They have a pleasant smell similar to vanilla. The structure of chalcone is shown below:
Melting point and solubility of chalcone
such as ethanol and water, than in nonpolar solvents, such as hexane and benzene. This is because chalcone has both polar and nonpolar parts in its structure. The polar part is the ketone group, which can form hydrogen bonds with polar solvents. The nonpolar part is the benzene rings, which can interact with nonpolar solvents through van der Waals forces.
Spectral analysis of chalcone
The spectral analysis of chalcone can be done using infrared spectroscopy and nuclear magnetic resonance spectroscopy. These techniques can provide information about the functional groups and protons present in chalcone. Here are the expected spectra of chalcone and their interpretations:
The infrared spectrum of chalcone shows the following peaks:
A strong peak at 1660 cm, which corresponds to the C=O stretching vibration of the ketone group.
A medium peak at 1600 cm, which corresponds to the C=C stretching vibration of the double bond.
A weak peak at 3050 cm, which corresponds to the C-H stretching vibration of the aromatic rings.
A weak peak at 1500 cm, which corresponds to the C-H bending vibration of the aromatic rings.
The nuclear magnetic resonance spectrum of chalcone shows the following signals:
A singlet at 2.5 ppm, which corresponds to the three protons of the methyl group attached to the ketone group.
A doublet at 7.8 ppm, which corresponds to the two protons of the benzene ring that are ortho to the ketone group.
A triplet at 7.6 ppm, which corresponds to the two protons of the benzene ring that are meta to the ketone group.
A doublet at 8.0 ppm, which corresponds to the two protons of the benzene ring that are ortho to the aldehyde group.
A singlet at 10.0 ppm, which corresponds to the one proton of the aldehyde group.
Applications
Chalcone as an intermediate for other compounds
Chalcone can be used as an intermediate for the synthesis of many other flavonoids, such as flavones, flavanones, flavonols, anthocyanins, and catechins. These compounds have various colors, flavors, and biological activities that make them useful for various industries. For example, flavones are yellow pigments that are found in many flowers and fruits. Flavanones are precursors for citrus flavonoids that have antioxidant and anti-inflammatory effects. Flavonols are found in tea, wine, and chocolate and have anticancer and neuroprotective effects. Anthocyanins are red, blue, or purple pigments that are found in berries, grapes, and red cabbage. They have antioxidant and anti-diabetic effects. Catechins are found in green tea and have anticancer and antimicrobial effects.
Chalcone as an antioxidant and anti-inflammatory agent
Chalcone itself has some antioxidant and anti-inflammatory properties that make it beneficial for health and wellness. Antioxidants are substances that can prevent or reduce oxidative stress caused by free radicals. Free radicals are unstable molecules that can damage cells and tissues and cause aging and diseases. Anti-inflammatory agents are substances that can reduce inflammation caused by infections or injuries. Inflammation is a natural response of the immune system to fight off pathogens or heal wounds. However, excessive or chronic inflammation can cause pain, swelling, redness, and tissue damage.
Chalcone can act as an antioxidant by scavenging free radicals or enhancing the activity of antioxidant enzymes in the body. Chalcone can also act as an anti-inflammatory agent by inhibiting the production or action of inflammatory mediators, such as cytokines, prostaglandins, and nitric oxide. Chalcone can also modulate the expression or activity of inflammatory genes, such as NF-kB, COX-2, and iNOS. By doing so, chalcone can protect the cells and tissues from oxidative stress and inflammation and prevent or treat various diseases, such as diabetes, cardiovascular diseases, neurodegenerative diseases, and cancer.
Chalcone as an anticancer and antimicrobial agent
Chalcone also has some anticancer and antimicrobial properties that make it useful for medical and pharmaceutical applications. Anticancer agents are substances that can prevent or treat cancer by killing or inhibiting the growth of cancer cells. Antimicrobial agents are substances that can prevent or treat infections by killing or inhibiting the growth of microorganisms, such as bacteria, fungi, viruses, and parasites.
Chalcone can act as an anticancer agent by inducing apoptosis or programmed cell death in cancer cells. Apoptosis is a natural process that eliminates damaged or unwanted cells from the body. Chalcone can also act as an anticancer agent by inhibiting angiogenesis or the formation of new blood vessels that supply nutrients and oxygen to tumors. Chalcone can also act as an anticancer agent by modulating the expression or activity of oncogenes or tumor suppressor genes, such as p53, Bcl-2, and c-Myc. By doing so, chalcone can interfere with the survival, proliferation, invasion, and metastasis of cancer cells.
Chalcone can act as an antimicrobial agent by disrupting the cell membrane or cell wall of microorganisms. The cell membrane or cell wall is a protective barrier that maintains the integrity and function of the cell. Chalcone can also act as an antimicrobial agent by interfering with the synthesis or function of essential biomolecules, such as DNA, RNA, proteins, and enzymes. Chalcone can also act as an antimicrobial agent by enhancing the activity of the immune system or synergizing with other antimicrobial agents. By doing so, chalcone can kill or inhibit the growth of microorganisms and prevent or treat infections.
Conclusion
In conclusion, chalcone is a simple aromatic ketone that has a wide range of applications in various fields. It can be synthesized from acetophenone and benzaldehyde using a simple and efficient procedure. It has some interesting characteristics and properties that can be analyzed using spectral techniques. It also has some valuable biological activities that make it beneficial for health and wellness, medical and pharmaceutical applications. If you want to learn more about chalcone or try to synthesize it yourself, you can download the PDF file of the synthesis procedure from this link: https://www.researchgate.net/publication/333791414_Synthesis_of_Chalcones_from_Acetophenone_and_Benzaldehyde.
FAQs
What are the advantages of synthesizing chalcone from acetophenone and benzaldehyde?
Some of the advantages of synthesizing chalcone from acetophenone and benzaldehyde are:
The procedure is simple and easy to follow.
The materials and equipment needed are cheap and readily available.
The reaction is fast and efficient.
The yield and purity of chalcone are high.
The product is versatile and useful for various applications.
What are the possible side effects or hazards of chalcone?
Some of the possible side effects or hazards of chalcone are:
Chalcone may cause allergic reactions in some people who are sensitive to it.
Chalcone may interact with some medications or supplements that affect blood clotting, blood pressure, blood sugar, or liver function.
Chalcone may have estrogenic effects that may affect hormone levels or reproductive health.
Chalcone may have cytotoxic effects that may affect normal cells as well as cancer cells.
Chalcone may have mutagenic effects that may cause DNA damage or genetic mutations.
How can I download the PDF file of the synthesis procedure?
333791414_Synthesis_of_Chalcones_from_Acetophenone_and_Benzaldehyde. You will need to create a free account on ResearchGate or log in with your existing account. Then, you can click on the "Download full-text PDF" button and save the file on your device.
Where can I buy acetophenone and benzaldehyde?
You can buy acetophenone and benzaldehyde from online or offline chemical suppliers or distributors. Some examples of online chemical suppliers are Sigma-Aldrich, Fisher Scientific, and Alfa Aesar. Some examples of offline chemical suppliers are local pharmacies, hardware stores, or hobby shops. You should check the availability, quality, price, and delivery options of the products before buying them. You should also follow the safety and storage guidelines provided by the suppliers.
How can I test the purity and quality of chalcone?
You can test the purity and quality of chalcone by using various methods, such as:
Melting point determination: A pure compound has a sharp and consistent melting point that matches the literature value. An impure compound has a lower and broader melting point that deviates from the literature value.
Solubility test: A pure compound dissolves completely in a suitable solvent without leaving any residue or color. An impure compound may leave some residue or color in the solvent or may not dissolve at all.
Color test: A pure compound has a uniform and clear color that matches the literature value. An impure compound may have a different or mixed color that deviates from the literature value.
Spectral analysis: A pure compound has a spectrum that matches the literature value and shows only the peaks or signals that correspond to its functional groups and protons. An impure compound may have a spectrum that deviates from the literature value and shows extra peaks or signals that correspond to impurities or contaminants.
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