Aug. 04, 2021
Cinnamic acid is a central intermediate in the biosynthesis of a myriad of natural products including signals (precursors to lignin and lignocellulose), flavonoids, isoflavonoids, coumarins, aurones, stilbenes, catechin, and phenylpropanoids. Its biosynthesis involves the action of the enzyme phenylalanine ammonia-lyase (PAL) on phenylalanine.
It is obtained from oil of cinnamon, or from balsams such as storax. It is also found in shea butter. Cinnamic acid(CAS No.: 140-10-3) has a honey-like odor; it and its more volatile ethyl ester (ethyl cinnamate) are flavor components in the essential oil of cinnamon, which is related to cinnamaldehyde is the major constituent.
Cinnamic acid was first synthesized by the base-catalyzed condensation of acetyl chloride and benzaldehyde, followed by hydrolysis of the acid chloride product. In 1890, Rainer Ludwig Claisen described the synthesis of ethyl cinnamate via the reaction of ethyl acetate with benzaldehyde in the presence of sodium as a base. Another way of preparing cinnamic acid is by the Knoevenagel condensation reaction. The reactants for this are benzaldehyde and malonic acid in the presence of a weak base, followed by acid-catalyzed decarboxylation. It can also be prepared by oxidation of cinnamaldehyde, condensation of benzal chloride and sodium acetate (followed by acid hydrolysis), and the Perkin reaction.
Cinnamic acid has many uses in medicine, perfumery, polymers, cosmetics, and agriculture.
Cinnamic acid is present in most green plants and has low toxicity. It is used in fragrances and in the manufacture of methyl, ethyl, and benzyl esters used in the perfume industry. It is also the precursor of the sweetener aspartame. Cinnamic acid has been reported to have antioxidant and antibacterial activities. This acid and its hydroxylated derivatives have been reported to have antifungal activity, preventing fungal spore germination and anti-tyrosinase activity with potential whitening activity. You can learn more by checking out a recent article we wrote: Cinnamic Acid Uses.
Use of Cinnamic Acid
Like other phenolic acids, such as gallic acid, cinnamic acid has been reported to have anticancer activity. It induces cell arrest and reverses the malignant properties of human tumor cells in vitro; it is a differentiation inducer of melanoma cells disrupting the cytoskeleton and inducing apoptosis and proliferation of nasopharyngeal carcinoma cells and leukemia cells in vitro. Hydroxylated cinnamic acid derivatives have antioxidant properties against coumaric acid and are believed to reduce the risk of gastric cancer by reducing the formation of carcinogenic nitrosamines. In addition, p-coumaric acid found in honey has in vitro anti-inflammatory activity.
Cinnamic acids form a relatively large family of organic acids that appear to have antibacterial, antifungal, and antiparasitic activities. They are also used in macromolecular synthesis and have attractive properties as very important structural units for various types of polymers, especially for their high photoreactivity due to the presence of cinnamic acyl groups (well known light-responsive units) in the main or side chains. Polymers containing the cinnamoyl fraction are widely used in emerging fields such as advanced microelectronics, photolithography, nonlinear optical materials, integrated circuit technology, and photocurable coatings.
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