Review of dibenzalacetone synthesis and its biological activities.

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Journal name: World Journal of Pharmaceutical Research
Original article title: Review on synthesis of dibenzalacetone from benzaldehyde by claisen-schmidt reaction and their biological activities
The WJPR includes peer-reviewed publications such as scientific research papers, reports, review articles, company news, thesis reports and case studies in areas of Biology, Pharmaceutical industries and Chemical technology while incorporating ancient fields of knowledge such combining Ayurveda with scientific data.
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Original source:

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Author:

Jadhav Sanika D., Lokhande Rahul P. and Hilal Nikita E.


World Journal of Pharmaceutical Research:

(An ISO 9001:2015 Certified International Journal)

Full text available for: Review on synthesis of dibenzalacetone from benzaldehyde by claisen-schmidt reaction and their biological activities

Source type: An International Peer Reviewed Journal for Pharmaceutical and Medical and Scientific Research

Doi: 10.20959/wjpr20235-27516


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Summary of article contents:

1) Introduction

The synthesis of dibenzalacetone, a compound of substantial chemical interest, is primarily achieved through the Claisen-Schmidt reaction, which represents a mixed aldol condensation between an aldehyde (benzaldehyde) and a ketone (acetone) in the presence of a base catalyst like sodium hydroxide. This reaction is significant in organic chemistry as it generates carbon-carbon bonds by reacting enolizable aldehydes and ketones. The resulting dibenzalacetone is characterized by its broad range of biological activities, including antibacterial, antifungal, antioxidant, antimalarial, analgesic, and antitumor properties.

2) Aldol Condensation Mechanism

The aldol condensation mechanism involving dibenzalacetone formation showcases the reactivity of aldehydes compared to ketones. In the presence of sodium hydroxide, the more reactive aldehyde carbonyl undergoes a condensation reaction with the enolate anion of acetone. This leads to the formation of a β-hydroxyketone, which is subsequently dehydrated to yield dibenzalacetone. The efficacy of this reaction is further enhanced by the stabilization provided by conjugation with both the carbonyl and the aromatic ring. This reaction allows for the formation of dibenzalacetone via a double mixed-aldol condensation, highlighting the versatility of this compound in organic synthesis.

3) Conventional Methods of Synthesis

Numerous conventional methods for synthesizing dibenzalacetone have been documented, employing various specific procedures to optimize yield and purity. For instance, one method involves dissolving sodium hydroxide in an ethanolic solution, followed by the incremental addition of benzaldehyde and acetone, maintaining a controlled temperature. Another technique includes the use of an ice-water bath to regulate reaction conditions, allowing for efficient precipitation of dibenzalacetone. Each method underscores the importance of reaction conditions—such as temperature, catalyst concentration, and reactant ratios—in achieving a successful synthesis.

4) Biological Activities and Applications

Dibenzalacetone exhibits considerable biological activities, making it a compound of interest in medicinal chemistry. Its antibacterial and antifungal properties have been established through assays against common bacteria like E. coli and S. aureus, as well as various fungal strains. Additionally, it has shown potential in antiparasitic activity against Leishmania donovani. Beyond these biological properties, dibenzalacetone serves functional roles in cosmetic formulations as a UV blocker in sunscreens and is applied in the creation of organometallic complexes used as catalysts in various chemical reactions.

5) Conclusion

The synthesis of dibenzalacetone through aldol condensation presents a valuable synthetic pathway with implications in both academic research and industrial applications. Its diverse biological activities open avenues for exploring its potential as a therapeutic agent. Additionally, understanding the versatility and reactions involved in its synthesis can inspire further research into related compounds and their applications. Continued exploration of dibenzalacetone may reveal more about its biochemical properties and broaden its utilization in pharmaceuticals and materials science.

FAQ section (important questions/answers):

What is dibenzalacetone and how is it synthesized?

Dibenzalacetone is a compound synthesized through the Claisen-Schmidt reaction, which involves the condensation of two equivalents of benzaldehyde with one equivalent of acetone in an alkaline solution, typically using sodium hydroxide as the base.

What are the biological activities of dibenzalacetone?

Dibenzalacetone exhibits a wide range of biological activities, including antifungal, antioxidant, antimalarial, analgesic, and antitumor characteristics, making it a subject of interest in pharmaceutical research.

What are the methods for the synthesis of dibenzalacetone?

Various methods exist for synthesizing dibenzalacetone, including using sodium hydroxide in aqueous ethanol, employing different reactant ratios, and controlling the reaction temperature during the process to enhance yield.

What is the role of dibenzalacetone in sunscreens?

Dibenzalacetone is used in sunscreens due to its ability to absorb harmful UV light, helping to protect the skin from ultraviolet radiation damage.

How is the antibacterial activity of dibenzalacetone assessed?

Antibacterial activity is evaluated by screening against microorganisms like E. coli and S. aureus, comparing inhibition of growth produced by dibenzalacetone with that of known antibacterial agents.

What is the molecular formula and properties of dibenzalacetone?

Dibenzalacetone has the molecular formula C17H14O, appears as a yellow crystalline solid, with a melting point of 112°C and is soluble in organic solvents like ethanol.

Glossary definitions and references:

Scientific and Ayurvedic Glossary list for “Review of dibenzalacetone synthesis and its biological activities.”. This list explains important keywords that occur in this article and links it to the glossary for a better understanding of that concept in the context of Ayurveda and other topics.

1) Water:
Water, often used as a solvent in organic synthesis, plays a critical role in chemical reactions, including the synthesis of dibenzalacetone. Its ability to dissolve reactants and help control temperature conditions is vital for achieving desired reaction yields and purity in the final product.

2) Activity:
The term 'activity' refers to the biological activity of compounds, such as dibenzalacetone, against various microorganisms. The study of these activities is essential for evaluating the potential therapeutic applications of the synthesized compounds, including antibacterial, antifungal, and antiviral properties.

3) India:
India is the location where the research on the synthesis of dibenzalacetone was conducted. The diversity of medicinal plants and chemistries in India provides a rich backdrop for pharmaceutical research, contributing significantly to global knowledge in synthetic organic chemistry and biological activities.

4) Antibiotic (Antibacterial):
Anti-bacterial refers to the property of a compound to counteract bacterial infections. The exploration of dibenzalacetone's anti-bacterial capacity is vital for its potential application as a therapeutic agent, providing insights into its efficacy against harmful bacteria.

5) Pune:
Pune is a city in Maharashtra, India, where the research study took place. It is known for its academic institutions and pharmaceutical industry, making it a hub for chemical research and innovation, particularly in organic synthesis and its applications in medicinal chemistry.

6) Relative:
The term 'relative' is crucial in scientific studies to convey the comparison of properties or activities among substances. This allows researchers to quantify the effectiveness and performance of compounds like dibenzalacetone in biological assays compared to established standards.

7) Maharashtra (Maharastra, Maha-rashtra):
Maharashtra is a state in India that encompasses Pune, where the research was conducted. The state has a robust pharmaceutical and research community, facilitating advancements in drug development and organic synthesis, which are pivotal for medicinal chemistry.

8) Karnataka:
Karnataka is another state in India known for its vibrant pharmaceutical sector and research institutions. It contributes to the broader context of medicinal chemistry in India, where studies on compounds like dibenzalacetone are integral to developing new therapeutic agents.

9) Chauhan:
Chauhan is a common surname in India, possibly referring to researchers or authors involved in the studies on dibenzalacetone. Notable individuals with this surname may be credited for their contributions to the understanding of the compound's synthesis and biological applications.

10) Aureus:
Staphylococcus aureus is a species of bacteria known for its role in various infections. The antibacterial activity of dibenzalacetone is typically assessed against this pathogen to evaluate its potential as an antimicrobial agent in treating infections caused by resistant bacteria.

11) Kumar:
Kumar is a widespread surname in India, often associated with authors or researchers in literature regarding pharmaceutical chemistry. It may indicate individuals involved in the synthesis of dibenzalacetone or its pharmacological studies, contributing to overall scientific progress.

12) Holla:
Holla may refer to either a researcher involved in the studies on dibenzalacetone or be significant in previous literature regarding its synthesis and biological activities. Individuals with this name could contribute to exploring its medicinal properties and applications.

13) New Delhi:
New Delhi, the capital of India, serves as a center for policy and research related to pharmaceuticals. Many national research organizations and universities are located here, contributing to advancements in drug discovery, including studies related to dibenzalacetone.

14) Measurement:
Measurement in the context of this research pertains to quantifying the biological activities of dibenzalacetone, such as its efficacy against bacteria and fungi. Accurate measurement methods ensure reliable data, essential for validating the compound's potential uses.

15) Observation:
Observation is a key aspect of scientific research, wherein researchers closely monitor reactions, yields, and biological effects of dibenzalacetone. Detailed observations lead to important conclusions regarding the effectiveness and stability of synthesized compounds during experiments.

16) Shivananda (Sivananda, Shiva-ananda):
Shivananda may be associated with a researcher mentioned in the context of dibenzalacetone studies. Individuals with this name may have played a role in investigating its synthesis, properties, or biological applications, contributing to the expanded understanding of the compound.

17) Substance:
In the scope of the research, 'substance' refers to the physical matter being studied, namely dibenzalacetone. The understanding of its chemical structure and properties influences its applications in pharmaceuticals and helps define its biological impact.

18) Education:
Education in the context of this research reflects the academic background and training of the researchers involved in the synthesis and analysis of dibenzalacetone. A strong educational foundation in chemistry facilitates advancements in pharmaceutical development.

19) Shirisha (Sirisa, Shirisa, Sirisha):
Sirisha may refer to a researcher engaged in the study of dibenzalacetone, particularly in its synthesis or evaluation of biological activities. Their contributions can enrich the scientific community's understanding of this compound’s potential applications.

20) Varsha (Varsa):
Varsha is likely a researcher or author involved in the exploration of dibenzalacetone. Contributions from individuals with this name can provide insights into the efficacy and safety of dibenzalacetone in various medicinal applications.

21) Malini:
Malini could refer to a researcher connected to the synthesis or pharmacological evaluation of dibenzalacetone. Their work may help elucidate the compound's biological effects and enhance the understanding of its therapeutic potential.

22) Kumari:
Kumari is a common surname in India and may refer to a researcher in the fields of medicinal chemistry or organic synthesis. Contributions from individuals with this name are vital to advancing knowledge about dibenzalacetone.

23) Parikh:
Parikh possibly represents an author or researcher linked to studies involving dibenzalacetone synthesis or biological evaluations. Their participation could contribute to the depth of knowledge regarding the compound's activities and applications.

24) Sanika (Shanika):
Sanika indicates a researcher involved in the study of dibenzalacetone. Their efforts may focus on the compound's synthesis, characterization, or evaluation of biological activities, contributing to the advancement of pharmaceutical research.

25) Nature:
Nature refers to the inherent characteristics and properties of dibenzalacetone, influencing its behavior in chemical reactions and biological systems. Understanding these natural properties is essential for developing effective pharmaceuticals.

26) Silver:
Silver may refer to a compound or complex involving dibenzalacetone, particularly in organometallic chemistry. The interaction of dibenzalacetone with metals can be crucial for developing new materials or catalysts for various chemical reactions.

27) Delhi:
Delhi, as the capital city, is vital for research and development in India’s pharmaceutical field. Many educational and research institutions here work on compounds like dibenzalacetone, exploring their significance in medicinal chemistry and drug development.

28) Patel:
Patel is a common surname in India, possibly related to researchers associated with the synthesis or study of dibenzalacetone. Such contributors can play a key role in advancing studies of the compound's properties and efficacy.

29) Chang:
Chang may represent a researcher involved in the characterization or study of dibenzalacetone and its derivatives. Scholars with this name might have published work focused on the methods and results of synthesizing this significant compound.

30) Table:
Table often denotes organized data presentation, such as properties or biological activity of dibenzalacetone. Structured data aids in understanding the compound's characteristics and is essential for comparisons in scientific research.

31) Death:
Death, in a biological context, may relate to the mortality of pathogens as a measure of the effectiveness of dibenzalacetone. Evaluating how the compound affects microbial viability is crucial for assessing its potential therapeutic applications.

32) Study (Studying):
Study refers to the systematic investigation of dibenzalacetone, encompassing its synthesis, characterization, and biological activities. Research studies contribute to the overall scientific understanding of the compound and pave the way for potential medicinal uses.

33) Hull:
Hull may refer to a researcher who has explored aspects of dibenzalacetone, particularly regarding its chemistry or synthesis techniques. Contributions by such individuals can influence the methodology and approaches taken in pharmaceutical studies.

34) Drug:
Drug signifies any chemical substance used for treatment, relief, or prevention of diseases. Dibenzalacetone's potential as a drug candidate highlights its importance in medicinal chemistry, particularly through its biological activities and applications in pharmacology.

Other Science Concepts:

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Discover the significance of concepts within the article: ‘Review of dibenzalacetone synthesis and its biological activities.’. Further sources in the context of Science might help you critically compare this page with similair documents:

Antibacterial activity, In vitro, Antifungal activity, Antibacterial activities, Well diffusion method, Chemical structure, Melting point, Biological activities, Boiling point, Sodium hydroxide, UV protection.

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