Chalcone is the

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

C₆H₅C(O)CH=CHC₆H₅. It is an α,β-unsaturated ketone. A variety of important biological compounds are known collectively as chalcones or

chalconoid Chalconoids ( Greek: χαλκός ''khalkós'', "copper", due to its color), also known as chalcones, are natural phenols In organic chemistry, phenols, sometimes called phenolics, are a class of chemical compounds consisting of one or more hy ...

s. They are widely known bioactive substances, fluorescent materials, and chemical intermediates.

Chemical properties

Chalcones have two absorption maxima at 280 nm and 340 nm.

Biosynthesis

Chalcones and chalconoids are synthesized in plants as

secondary metabolite Secondary metabolites, also called ''specialised metabolites'', ''secondary products'', or ''natural products'', are organic compounds produced by any lifeform, e.g. bacteria, archaea, fungi, animals, or plants, which are not directly involved ...

s. The enzyme

chalcone synthase Chalcone synthase or naringenin-chalcone synthase (CHS) is an enzyme ubiquitous to higher plants and belongs to a family of polyketide synthase enzymes (PKS) known as type III PKS. Type III PKSs are associated with the production of chalcones, a ...

, a type III

polyketide synthase Polyketide synthases (PKSs) are a family of multi- domain enzymes or enzyme complexes that produce polyketides, a large class of secondary metabolites, in bacteria, fungi, plants, and a few animal lineages. The biosyntheses of polyketides share ...

, is responsible for the

biosynthesis Biosynthesis, i.e., chemical synthesis occurring in biological contexts, is a term most often referring to multi-step, enzyme-Catalysis, catalyzed processes where chemical substances absorbed as nutrients (or previously converted through biosynthe ...

of these compounds. The enzyme is found in all "higher" (

vascular Vascular can refer to: * blood vessels, the vascular system in animals * vascular tissue Vascular tissue is a complex transporting tissue, formed of more than one cell type, found in vascular plants. The primary components of vascular tissue ...

) and several "lower" ( non-vascular) plants.

Laboratory synthesis

Chalcone is usually prepared by an aldol condensation between

benzaldehyde Benzaldehyde (C6H5CHO) is an organic compound consisting of a benzene ring with a formyl substituent. It is among the simplest aromatic aldehydes and one of the most industrially useful. It is a colorless liquid with a characteristic almond-li ...

and acetophenone. : This reaction, which can be carried out without any solvent, is so reliable that it is often given as an example of

green chemistry Green chemistry, similar to sustainable chemistry or circular chemistry, is an area of chemistry and chemical engineering focused on the design of products and processes that minimize or eliminate the use and generation of hazardous substances. Wh ...

in undergraduate education.

Potential pharmacology

Chalcones and their derivatives demonstrate a wide range of biological activities including anti-inflammation. Some 2′-amino chalcones have been studied as potential antitumor agents. Chalcones are of interest in

medicinal chemistry Medicinal or pharmaceutical chemistry is a scientific discipline at the intersection of chemistry and pharmacy involved with drug design, designing and developing pharmaceutical medication, drugs. Medicinal chemistry involves the identification, ...

and have been described as a privileged scaffold.

Uses

Medicinal uses

, chalcones have been used as: *

antioxidant Antioxidants are Chemical compound, compounds that inhibit Redox, oxidation, a chemical reaction that can produce Radical (chemistry), free radicals. Autoxidation leads to degradation of organic compounds, including living matter. Antioxidants ...

s * Anticancer agents *

antidiabetic drug Drugs used in diabetes treat types of diabetes mellitus by decreasing blood sugar level, glucose levels in the blood. With the exception of Insulin (medication), insulin, most GLP-1 receptor agonists (liraglutide, exenatide, and others), and pra ...

s *

antiviral drug Antiviral drugs are a class of medication used for treating viral infections. Most antivirals target specific viruses, while a broad-spectrum antiviral is effective against a wide range of viruses. Antiviral drugs are a class of antimicrobials ...

s * antimalarial drugs and more.

Industrial uses

In chemical industries, they are employed as: *

liquid crystal Liquid crystal (LC) is a state of matter whose properties are between those of conventional liquids and those of solid crystals. For example, a liquid crystal can flow like a liquid, but its molecules may be oriented in a common direction as i ...

s *

fluorescent Fluorescence is one of two kinds of photoluminescence, the emission of light by a substance that has absorbed light or other electromagnetic radiation. When exposed to ultraviolet radiation, many substances will glow (fluoresce) with color ...

chemical scaffolds * metal sensors *

corrosion inhibitor A corrosion inhibitor or anti-corrosive is a chemical compound added to a liquid or gas to decrease the corrosion rate of a metal that comes into contact with the fluid. The effectiveness of a corrosion inhibitor depends on fluid composition and ...

s *

plant hormone Plant hormones (or phytohormones) are signal molecules, produced within plants, that occur in extremely low concentrations. Plant hormones control all aspects of plant growth and development, including embryogenesis, the regulation of Organ (anat ...

Uses in organic chemistry

Chalcones have been used as intermediates in heterocyclic synthesis, especially in the synthesis of

pyrazole Pyrazole is an organic compound with the chemical formula, formula . It is a heterocycle characterized as an azole with a 5-membered ring of three carbon atoms and two adjacent nitrogen atoms, which are in Arene substitution pattern, ortho-substi ...

s and aurones.

References

External links

Chalcone on reference.md
{{Webarchive, url=https://web.archive.org/web/20200925011431/http://www.reference.md/files/D047/mD047188.html , date=2020-09-25 Chalconoids Phenyl compounds Enones